Vacation Condo Rentals By Owner In Key West, FL

OLD TOWN PARADISE....brParadise awaits in a cozy Truman Annex retreat. Set on a cozy lane that is off the beaten path but close enough to walk or ride your bicycle to restaurants, this unique gem offers your much needed tropical R&R!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter this sparkling, cozy abode through the front gate where a small porch with seating invites you for morning java and sultry island breezes. As you enter, a fully-equipped kitchen greets you which includes an electric stove, microwave, refrigerator, coffee maker, toaster oven, and kitchen bar area. Gather, drink and dine around the dining table for 4, then settle in the adjacent living room on your cozy sofa (pulls out as a sleeper) or cushioned chair and enjoy movies on a large flat-screen tv. Two sets of french doors welcome in the warmth and sunshine of tropical living and open to your private patio with grill and outdoor seating for 4. A convenient powder room is also located in the living area.brbrSLEEPING ARRANGEMENTS...brTravel up the stairs to two en-suite guest rooms when you're ready to rest and refresh for the next day's adventures. The primary bedroom features a king bed with dresser, small flat screen tv, a large closet for storage and hanging clothes and also includes a make-up vanity, ironing board, and iron. The private bathroom is equipped with a glass-door shower and sink cabinet with storage drawers. Open your french door to your own enchanting small terrace with two chairs and a table for quiet conversation or a date with your favorite novel. Walk down the upstairs hallway to the second bedroom which features a queen bed, flat screen tv, storage closet for hanging clothes and an additional dresser inside. The private bathroom offers a shower/tub combination and sink cabinet with storage drawers. The washer/dryer closet sits between the two bedrooms in the upstairs hallway.brbrOUTDOOR LIVING...brWalk through the living area french doors to your private outdoor area with seating for 4 and a gas grill, which is the perfect cocktail spot or for dining under the twinkling stars. Take a stroll through this attractive community which is just right around the corner from Fort Zachary Taylor State Park, Harry Truman’s Little White House and Truman Annex’s Waterfront Park. Swimming in the heated community pool is a great way to wash off the day and it's just around the corner from the unit. There is a cabana with restrooms in the pool area and plenty of lounging chairs for your sunbathing pleasure.brbrPARKING...brThis home does offer covered parking for one vehicle. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$1078.21

Elegance. Sophistication. Perfection.brbrWelcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Key West. Located on the picturesque and coveted William Street, this extraordinary residence embodies timeless charm, architectural grace, and modern luxury — a rare gem that truly stands apart.brbrBuilt in 1866, this iconic conch-style home was originally owned by the youngest son of prominent Bahamian settlers. With each ownership, the property has been meticulously restored and thoughtfully enhanced, preserving its historic footprint while seamlessly blending in tasteful, contemporary upgrades.brbrRecognized with architectural awards and revered as one of the most exquisite homes in the Key West Historic District, the Gideon Lowe House invites guests into a world where heritage meets comfort in the most elegant fashion.brbrPROPERTY HIGHLIGHTS:brbr- 3 Bedrooms | 3.5 Bathroomsbrbr- Award-Winning Historic Homebrbr- Original Dade County Pine Throughoutbrbr- Private Pool with Waterfall & Sun Deckbrbr- Off-Street Parking (1 space)brbr- Fully Fenced Front & Rear Yardbrbr- Prime Old Town Location – 4 Blocks from Duval St.brbrINDOOR FEATURESbrbrMain Floor:brbr- Expansive sitting porch & welcoming foyerbrbr- King guest suite with walk-in closet, flat-screen TV, and luxurious en-suite bath (tub & shower)brbr- Stylish powder roombrbr- Chef’s kitchen with premium finishesbrbr- Formal dining room ideal for entertainingbrbr- Spacious living room & back entertainment loungebrbr- Lush outdoor sitting area, private pool with waterfall, sun deck & loungersbrbrSecond Floor:brbr- Dedicated laundry room & office/landing areabrbr- Lavish primary suite with king bed, flat-screen TV, oversized walk-in closetbrbr- Spa-inspired bathroom with soaking tub & walk-in showerbrbr- Private balcony with cozy seatingbrbrThird Floor:brbr- Charming third bedroom with two twin bedsbrbr- Full bathroom with walk-in showerbrbr- Generous closet spacebrbrLOCATION, LOCATION, LOCATION: brbrNestled in the desirable Historic Seaport District, this home is just steps away from the very best of Key West — world-class dining, galleries, shops, and entertainment. Only four blocks from Duval Street, yet tucked away in a quiet residential enclave, the Gideon Lowe House offers unmatched convenience with serene privacy.brbrYOUR STAY:brbrWhether you're seeking a tranquil escape or a stylish base for island adventures, this remarkable residence delivers beyond expectations. From its storied past to its curated interiors and luxurious amenities, every detail has been designed with your comfort and experience in mind.brbrDon’t miss your chance to stay in one of the most captivating homes in Key West — where history, elegance, and tropical splendor come together in perfect harmony.

The Gideon Lowe House - Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$631.73

Living room, Dining room and kitchen all enjoy stunning views of the Atlantic Ocean. Master bedroom and Master bath also enjoy the same view. Additionally this end unit also has 3 windows on its east side letting in plenty of natural light and offering a larger feel to the unit than interior units. If the marina and yachts intrigue you simply walk downstairs through the gate to enter the marina. Sportfish yachts and large center consoles with multiple outboards will have you fantasizing or planning your next day on the water. Walk 100 yards North to Yellowfin Bar and Grill for a sit down meal overlooking Oceanside Marina. Or better yet go out on a fishing charter and have them cook your catch ! The property also offers kayaking, wet slip rentals, jet ski tours, boat rentals and much more. Large covered balcony with room to lounge in front of Ocean, enjoy a meal, or read a book in peace. 5 additional restaurants within 2 minutes Italian, Mexican, Cuban, & American cuisine. Condo comes with 2 assigned/covered parking spots. Drive 10 minutes to old town/Duval Street for a taste of the famous Key West night life and return to our peaceful slice of paradise. My name is Zach Bentley and I am happy to assist.

3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina

Key West, Florida, United States

Bed

Bath

Sleeps

$1406.93

Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay at this Island Chic property is filled with luxury and personalized touches. A home designed by a local and prestigious architect, amenities here offer a fully bountiful experience of extravagance that will make any visitor feel like a Key West celebrity.brTake a small flight of stairs up to the main floor to find stylish slate floors, professional Viking stainless steel appliances, and a bright and light sitting area. Wood cabinets meet with light furniture to provide an artistic contrast in the room only a designer can produce. A spacious, elevated dining room table completes the open concept look, along with a meticulously made wet bar, wine chiller and separate beverage fridge included. What makes this room unlike any other, however, is the view from the sitting area. Visitors of Island Chic, get their own piece of Garrison Bight, a protected body of water which accommodates the local charter fishing fleet alongside recreational pleasure boaters. This aquatic sight is accompanied by a bustling marina, peaceful highway, and a glimpse into the skyline from the main island. Take in the, offering the daily excitement that Key West provides without ever having to leave your home away from home.brThis diverse view can be seen throughout the entire house, from the living room, to the bedrooms, to the outdoor entertainment area. Make a cocktail at the wet bar, take a step outside on to the balcony with rustic patio furniture, and take a few steps down to find the outdoor living area on the ground floor. Fully equipped with wooden countertops and an outdoor bathroom, this area allows visitors to soak up the sun in their own private oasis. A vibrant and inviting suspended bench is the perfect spot for sipping away and planning a day out on the Island. To top it all off, a quaint pool directly facing Garrison Bight offers a Key West style elevated pool. Ponder about the daily adventures Garrison Bight offers to island natives. Enjoy the tranquility of this view at night, sprinkled with city lights and bright stars. Back inside the home, take the stairs decorated with local artwork up one floor to find two spacious en-suite bedrooms and the laundry room. King size beds with luxury sheets invite deep sleep and sweet dreams. Enjoy the professionally designed showers which make visitors feel like noblemen themselves. Long balconies with lounging furniture, Key West botanicals, and diverse views offer a daily lens into the island life. When the balcony experience has ended, close the blinds for a visitor’s choice of a dark or bright wake up. brWhat completes Island Chic, is the fully elegant and spacious top floor master suite, which is convertible into 4 twin beds. A firm and comfortable king bed, multiple windows, and two built-in closets offer a total superstar stay. A reading nook is tucked into the bay side of the master, with a cozy day bed and natural light that will accompany hours of lounging. The day bed accommodated a trundle, which provide for the optional twin beds. A dignified dressing room, with a large mirror and multiple built-in cabinets, leads the visitor to a fully-equipped en-suite bathroom. With a water closet, bidet, walk in shower built for two, and his and hers vanities, it is certainly the bathroom in the home that evokes jealously. To top off this room, are views of Key West native plants and the Garrison Bight, views just as diverse and enticing as the others, but from a higher perspective. Take a peak on what the day might be like on the Island, with just a flick of a plantation shutters from suite’s view.brIsland Chic offers a customizable luxury that can make any Key West vacation feel more elegant and over the top. With a modern theme that is intricately decorated with traditional finishes, located steps from island history, the glamour of a stay here is challenging not to enjoy.brDOG FRIENDLY. Please contact us to confirm specific pet policies.

Luxury 3-Bedroom Waterfront Home with Pool AND Dock!

Key West, Florida, United States

Bed

Bath

Sleeps

$304.43

Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West!brbrLocated in the charming Shipyard Condominium Complex at Truman Annex, this quaint and well-appointed first-floor condo offers the perfect blend of comfort and convenience. Featuring two bedrooms and one bathroom, it’s ideal for families or friends looking to explore Key West’s best attractions just steps away!brbrInside Your Home Away From Home:brbrSpacious Living Area: Relax on new full-size sofa (sleeper included), two comfy chairs, and enjoy your favorite shows on the 50” flat screen TV.brbrDining Room: Full-size table with seating for four—perfect for meals or game nights.brbrFully Equipped Kitchen: Includes refrigerator, dishwasher, oven, coffee maker, blender, toaster, and all the essentials you need.brbrGuest Bedroom: Two twin beds that can convert into a king on request, a closet, dresser, full-length mirror, and a flat screen Firestick TV.brbrMaster Bedroom: Queen bed, 50” flat screen TV, closet, dresser, and full-length mirror.brbrBathroom: Full-size shower/tub combo, vanity, and toilet.brbrLaundry Closet: Washer, dryer, and cleaning supplies for your convenience.brbrStep Outside:brbrEnjoy a huge back deck with seating, a table, umbrella, and two cruiser bikes to explore the island. Lush, mature landscaping surrounds the condo, creating a serene environment with walking paths and easy pedestrian access through Truman Annex.brbrCommunity Perks:brbrAssigned parking spot right in front of your unit.brbrSecure gated community with code entry.brbrPool area with loungers, towels, and restroom access.brbrAccess to Truman Annex pedestrian gates via foot gate keys.brbrPrime Location:brbrWalk or bike less than 2 blocks to Truman’s Little Whitehouse and the iconic Green Parrot. Less than 1 mile from Fort Zachary Taylor Beach, Mallory Square, Duval Street, the Southernmost Point, Hemingway House, and more!brbrLeave your car behind and enjoy Key West at your own pace. Whether it’s your first visit or a beloved return, Keys to Paradise offers the ideal home base for your unforgettable island getaway.

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Key West, Florida, United States

Bed

Bath

Sleeps

$632.79

Welcome to The Secret Grotto — Your Luxurious Tropical Escape!brbrStep into this stunning 3,220-square-foot sanctuary nestled on nearly 5,000 square feet of lush, private paradise. This spacious Key West retreat boasts 3 oversized bedrooms, 4 full bathrooms, and an entertainer’s dream layout designed for unforgettable moments with family and friends.brbrInside, be wowed by the chef’s kitchen—gleaming with top-of-the-line Viking appliances including a 48-inch gas range, built-in steamer, wine cooler, and rich Cherry cabinetry—perfect for crafting gourmet meals or casual island snacks. The open-concept living and entertainment area flows effortlessly, ideal for relaxing or hosting lively gatherings.brbrStep outside through two grand sliding doors to your own tropical oasis. Lounge by the expansive lagoon-style pool complete with a mesmerizing grotto waterfall, or unwind on sun-kissed loungers and dine alfresco with seating for eight under the open sky. Private, fully fenced, and inviting—this backyard paradise is your personal slice of island heaven.brbrUpstairs, discover three sumptuous en-suite bedrooms designed for ultimate comfort and privacy. The primary suite pampers you with a king-size bed, cozy sitting area, smart TV, a private balcony overlooking the pool, and a spa-inspired bathroom featuring a jacuzzi tub, dual vanities, and a spacious walk-in closet.brbrTwo additional guest suites offer king and queen beds, elegant sitting areas, smart TVs, and luxurious bathrooms with walk-in closets, ensuring every guest feels right at home.brbrAdditional amenities include a two-zone HVAC system for perfect climate control, impact windows and sliding doors for tranquility and safety, plus secured off-street parking for two vehicles.brbrLocation is everything: Situated in vibrant Mid-Town Key West, you’re just minutes from pristine beaches, iconic landmarks like the Southernmost Point, Mallory Square, the buzzing 200 Block of Duval Street, and a variety of top-notch dining and nightlife options. Whether you prefer a vehicle or golf cart, everything you want is within easy reach.brbrBonus: Heat your private pool during cooler months (November 15 - May 1) for just $20 per day—perfect for year-round luxury.brbrThe Secret Grotto is more than a vacation home — it’s your personal island retreat, combining spacious elegance, upscale finishes, and unbeatable location to create a getaway you’ll want to return to again and again.

The Secret Grotto

Key West, Florida, United States

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Bath

Sleeps

$1863.73

When you enter the gate next to the painted 1306 sign, you’ll find yourself immersed in this one-of-a-kind tropical wonderland. Welcome to the Flower Power House, where Key West’s free spirit lives on in every colorful corner. Built in 1938 and reinvented over decades by its owner-artists, this isn’t your average vacation rental—it’s an ever-evolving, artful hideaway with handmade details and a playful maze-like layout that invites discovery. Each door leads somewhere fun: a cozy sleeping porch, a pastel pink seashell carriage house, or a sunlit loft tucked under open-beam ceilings. Forget hotel perfection; here, charm comes from bespoke creativity and the joy of offbeat island treasures.brbrInside, you’ll find six bedrooms spread across three interconnected spaces. French doors open nearly every room to breezy porches, and no two rooms are alike—think tropical colors, original art, funky shapes and textures, and vintage finds that harken back to the “good ol‘ days” of quite a “hippy” Key West. Play games in the spacious living area under soaring cathedral ceilings, cook together in two kitchens plus a kitchenette, or sneak off to a private nook with a book to unwind. The vibe is eclectic, colorful, and quirky—perfect for guests who appreciate artful character over a predictable, commercialized feel. brbrOutside, you’ll waltz through the thriving foliage crafted by the owner’s own hands—an enchanting backyard full of winding walkways, darting lizards, and layers of tropical plants that feel part garden, part storybook. Covered porches wrap around the home on both levels, inviting long conversations and slow mornings. Just beyond, a massive 40’ swimming pool glimmers in the sun ready for splashing and cooling off. Please note the pool is shared with only the two neighboring townhomes. If you are interested in renting one of the townhomes as well, please inquire about renting our Family Reunion Compound property! This includes both Flower Power House and the Coco’s Poolside Retreat townhome for hosting even more friends and family!brbrThe Flower Power House is truly unique. Tucked in the heart of the White Street Gallery District, you’re a short walk or bike ride to local cafés, art galleries, the beach. Coming back to the Flower Power House after a night out adventuring on Duval Street and beyond is a blast. If you love places that are soulful, creative, and a little askew, the Flower Power House is your perfect home base for making awesome vacation Key West vacation memories!brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

The Flower Power House - Boho Beautiful

Key West, Florida, United States

Bed

Bath

Sleeps

$816.49

Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key West. Designed as a creative complement to its neighbor, the Flower Power House, this laid-back retreat is situated in a tropical wonderland of a yard and walks right out to a huge, sparkling 40’ swimming pool shared with only two other homes—making it feel both social yet private. With porches on the first and second floors looking right out over the gardens, there’s always a sunny spot to sip morning coffee or evening cocktails after exploring the best of Key West.brbrInside, bright island colors, handmade art, and whimsical details create a fun, welcoming vibe across all three levels. The main floor’s open living area is nice for gathering, with a fully equipped kitchen and half bath. Upstairs, the second floor has a queen bedroom and a separate sitting room with a queen sleeper sofa, both opening onto a wide porch with views of the pool and yard. The top floor has two more bedrooms—one with a king bed and another with two twins (convertible to a king)—plus a Jack and Jill bathroom, making it easy for families or friends to spread out.brbrCoco’s Poolside Retreat feels like a perfect hideaway set off the street and hidden behind the big white gate and lush trees, yet you’re right in the White Street Gallery District. Most of your neighbors are local, full time residents making for a peaceful vibe, but a short walk or quick bike ride gets you to the beaches, art galleries, cafés, and local favorites like Salute on the Beach. It’s a perfect home base for guests who love a tropical, local feel, a bit of whimsy and a great pool. Book Coco’s Poolside Retreat to soak up Key West’s colorful, laid-back spirit, and look into booking the Flower Power House as well, for the complete Family Reunion Compound if the whole crew is coming along!brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Coco's Poolside Retreat

Key West, Florida, United States

Bed

Bath

8

Sleeps

$204.96

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOZY VALUE IN TRUMAN ANNEX…brThis 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This small but sensational gem is an upstairs unit with all of the creature comforts you will need in paradise! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEasy breezy comfort greets you as you enter this charming home. Travel up the carpeted stairs to a bright and cheerful open living room and kitchen/dining space. Unwind on the plush furnishings as cheerful sunlight floods the living room and creates a happy and carefree environment. A smart TV offers a wide array of programming for your viewing indulgence. The dining/kitchen area is adjacent to the living room, with a dining table nearby. The kitchen is fully equipped with a dishwasher, stove, microwave, refrigerator and both a Keurig and drip coffee maker. The cabinets are stocked with every kitchen tool you will need to craft delicious meals. brbrSLEEPING ARRANGEMENTS…brUnwind from your day of island fun in the king bedroom. A wall-mounted smart tv is available for lazy days when it just feels right to linger in your cozy bedding and binge on your favorite shows. The storage closet houses a fold-up twin bed and extra bath linens for your enjoyment. The bathroom is next door with a glass-door shower and a washer/dryer closet is adjacent to it for your convenience.brbrOUTDOOR LIVING…brThe Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door to the roomy private terrace, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for 2 where you can have your morning coffee or enjoy a cocktail after a long day of exploring. There are also 2 more cushioned wicker chairs for lounging outdoors.brbrPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet feebrbrBOOKING DATES... brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCOME STAY A WHILE...

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

Key West, Florida, United States

Bed

Bath

Sleeps

$406.83

28 DAY MINIMUM RENTAL! brRENTALS START ON 1ST DAY OF MONTH!brbrHistoric unit - RENTALS START ON THE 1ST DAY OF MONTH!brHistoric Caribbean Cottage is an Historic Bahamian house that has been completely renovated December, 2018. Located on a 2 block long lane situated between Duval Street and Simonton Streets, just off U.S. 1 (Truman Avenue).brbrSit on the front porch with 2 rocking chairs and a porch swing and watch people strolling down the street and listen to the soothing sounds of the blue water fountain in the front garden. There is a bicycle lock up in the front, too. brbrWalk inside the living room and be greeted with “Caribbean” blue walls with a custom made sleeper sofa (5” memory foam mattress) with an under water critter motif. Relax in the blue swivel bucket chair with foot stool while watching the 56” Smart TV to watch sports or your favorite channels. Bring your Sling, Netflix and Prime passwords to watch TV/movies on our newly provided 5G fiber optic WiFi. A small chest with pull out shelf for computer work is also provided as well as office chair. Local art completes the “relaxed” attitude of this living space.brbrThe front bedroom off the hall features a king deluxe memory foam bed, Pottery Barn furniture with pull out baskets under the bed for extra storage. Custom sea glass art by Robin Renee Hix adorns the walls and another 56” Smart TV is on the wall facing the bed. There is a makeup vanity/desk, Pottery Barn closet and storage for your convenience. USB ports are on the bedside lamps and wall. brbrWalk down the hall to the colorful bathroom on the right. Tiled in a rainbow of muted colors, a 17” high toilet for your comfort, shower with magnetic shower head to wash your furry friends if you bring them, Tommy Bahamian body wash, shampoo, conditioner and body lotion is also provided for your total comfort. Beach towels, bath towels in a lovely shade of blue complete this bath.brbrThe custom kitchen with beautiful quartz counter tops will dazzle you! Appliances included are refrigerator/ice maker, garbage disposal, glass top stove and microwave. Everything needed to cook/bake a gourmet meal are provided including blender, food processor, Vita Mix, pots, pans, drink glasses, sharp knives, cutting boards, drip coffee maker, toaster, etc. Sit at the custom 2 person bar for coffee with swivel bar stools and charge phones/pads in the USB ports. There is a Bluetooth speaker there if you want to listen to news or a podcast while enjoying waking up.brbrThe second bedroom/bath is at the rear of the cottage. Walk out the kitchen door under awnings and you will find the second king bedroom which is built over the historic cistern used for water collection in the past. More Pottery Barn furniture features a king deluxe memory foam mattress, bedside tables with USB connections and a large walk-in closet with a barn door covering the opening. On the wall facing the bed is another 56” Smart TV. The bathroom here also has a 17” high toilet with unique turquoise and navy blue glass on the floor. Ever taken an outdoor shower Well here you can in our tropical paradise! Totally private with hot/cold water and Tommy Bahama toiletries, enjoy watching the clouds float by or look at the nighttime stars! The shower also has another door that opens to the pool for your convenience.brbrIn the rear, tropical plants, including many different types of orchids, surround the heated pool which is private for your use from 5pm till 9am. From 9a-5p the Adults only pool is shared with my other guests and the gate is open for their use during this time. A locked gate at the side of the cottage provides privacy in the evenings. There is a second heated pool across the street for your use as well. On the rear deck is a table/6 chairs with a large rectangular umbrella to enjoy a meal outside as well as two outdoor lounge sofas to enjoy drinks and conversations. Washer/dryers are for your use, as well. A gas BBQ grill is on the deck outside the kitchen. brbrOther extras provided are free WiFi, Amazon Alexa’s in each room, central AC/heat, ceiling fans throughout, Dyson cordless vacuum and all cleaning/soap supplies. brbrBook this unit today to insure you have the best location to spend your month of vacation time on the perfect tropical Island getaway. Don’t forget Key West has bus transportation all around Old Town that runs every 15 minutes and we have a stop just a block away!brbrWe look forward to hosting you and making your vacation PERFECT!brbrTwo heated pools, the pool behind Caribbean Cottage is shared with my other guests daily from 9-5p. Your pool is private for your use from 5p-9a. The 4 washers/dryers are for your use. Weber Gas Grill. Bike lockup. The entire home is yours to enjoy.brbrI am always available by text and there are staff available 24/7 to assist you in any way.brbrIn the heart of Historic Old Town, yet quiet and secluded, there is a bike/moped rental at the corner of Center and Truman, a CVS, Drs. Office, Subway and dry cleaners across Truman at the entrance to Center Street. There are multiple restaurants, bars and attractions all around us. The sandy beach on the Atlantic side of the island is a short 5 block walk away with a restaurant/bar on the beach.brbrBike, moped, electric car or FREE bus will get you wherever you might want to go in Old Town plus we are within walking distance of most places you might want to visit.brbrFree wi-fi through out the property!brRental MUST begin on first day of month during Season (Jan-May) for a minimum of 28 days. During other times if the year checkin can be other times of the month.

Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools

Key West, Florida, United States

Bed

Bath

Sleeps

$1230.38

Summary:brbrExperience the heart of Key West from this charming Front Street retreatbrbrbrbrThe Space:brbrStay just steps from the action in this beautifully updated 1 bedroom, 1 bath apartment located above iconic Front Street in Old Town Key West. Perfect for up to four guests, this tropical escape blends modern comfort with unbeatable walkability to the island’s most exciting attractions.brbrbrbrWake up to warm island breezes on your balcony before stepping out to explore everything Key West has to offer — no car needed. Just one block from Mallory Square, you’re immersed in the island’s vibrant cultural hub. Enjoy world-famous sunsets with street performers, dine at local favorites like A&B Lobster House and Conch Republic, or sip cocktails at legendary bars including Captain Tony’s and Sloppy Joe’s.brbrbrbrSpend your days visiting the Key West Aquarium, Shipwreck Museum, and Audubon House, all just a short stroll away. Browse local art galleries, hop on a sunset cruise, or join snorkeling and fishing excursions departing from the marina right down the street.brbrbrbrInside, unwind in the comfortable king bedroom, prepare meals in the fully equipped kitchen, and relax in the bright, open living area with a sleeper sofa, flat-screen TV, and complimentary Wi-Fi. A private washer and dryer make extended stays easy and convenient.brbrbrbrOne free off-site parking space is available approximately three blocks away, and everything you need is within walking distance.brbrbrbr Small dog welcome with manager approval and a $250 non-refundable pet fee.brbrbrbr✨ A Note About the LocationbrbrThis apartment is located in a lively Old Town area near bars and live music — some evening and late-night noise may be heard, which is part of the authentic Key West experience. This home is best suited for guests who enjoy being close to the island’s energy and nightlife.brbrWhether you’re here for the sights, the history, or simply to soak up the island vibe, this Front Street retreat puts the very best of Key West right outside your door.

Apartment

Coral Reef Suite | 1 bed near Duval & waterfront

Key West, Florida, United States

Bed

Bath

Sleeps

$650.21

Summary:brbrTwo 1 - bedroom Suites close to beachesbrbrbrbrThe Space:brbrTwo- one bedroom private suites close to beaches

Atlantis House Suites

Key West, Florida, United States

Bed

Bath

Sleeps

$307.08

Take a break and unwind at this peaceful oasis. Full house rental on Big Coppitt Key, only 6 miles from Key West. Live the laid-back Keys lifestyle, or drive 15 minutes to be in the thick of the Key West action. Located in a quiet neighborhood, our fully appointed house will serve you well as your home-away-from-home. Open the back doors to fully enjoy the lush and private backyard with a waterfall, hot tub and pond.brbrDue to County regulations, we are NOT a nightly rental.brbrWe are situated in a quiet, older established neighborhood. Most of our neighbors have lived here for 20+ years. The house is surrounded by some of the best people on the planet. There are mature date palms, frangipani, hibiscus, a very large Strangler Fig, and several coconut palms. The large Tiare bushes in the front will provide you a beautiful fragrance when blooming as well as the large jasmine bush right off the patio in the back.brbrThere are two quiet bedrooms, both with queen sized beds. The primary bedroom in the back of the house, and has an en suite bath with a shower and glass block wall for loads of natural light. There's a walk-in closet with plenty of hangers and shelves, as well as a dresser in the bedroom. Open the french doors to capture our tropical breezes and listen to the sound of the waterfall.brbrThe front bedroom has its own dresser and a large closet with mirrored doors and plenty of hangers. There's a hall bath steps away with a tiled tub/shower unit.brbrThe living room is bright and sunny with comfy slip-covered furniture, a smart TV and Amazon Firestick, and library shelves with plenty of books for reading and relaxing.brbrThe sunny kitchen is well appointed for all your cooking needs. There's a gas range, side-by-side fridge with icemaker and dishwasher. Fully loaded with pots/pans, dishes and utensils, toaster, drip coffeemaker and blender.brbrHave your meals right outside the french doors of the dining room, or if weather doesn't permit, there's a dining table for four just inside. There's a charcoal grill available for cooking up your fresh catch or some nice juicy steaks.brbrIf you must work while you're here, there's a dedicated office space in the mudroom. The laundry room has a front load washer and dryer, and extra shelves for storage. There is off-street parking for two or three vehicles.

2BR 2 BA Big Coppitt Key

Key West, Florida, United States

Bed

Bath

4

Sleeps

$509.04

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSOUTHERN STAR is a modern Key West home nestled in the quiet Meadows neighborhood of Old Town that combines the island way and the sweet life of the South. With wide porches, a breezy interior, cathedral ceilings, and an apparent southern charm, it's easy to see where this home gets its name. In addition to its distinct southern features, this home also offers the best of modern amenities, including a beautifully renovated kitchen, a bonus loft, and a private pool and jacuzzi spa. SOUTHERN STAR combined with Last Key Realty's Five-Star Guest Services is sure to make your stay in Key West exceptional.brbrTHE LOCATION...brbrThe Meadows is a residential district of Old Town Key West. This quiet neighborhood with primarily residential homes and noiseless streets is perfect for peaceful evening strolls, but also within walking distance of the commercial area of White Street with restaurants, shops, and Fausto's grocery store. This home is located less than a mile from Duval Street, an easy bike ride or walk any day. Although you won't need a vehicle to get around from this ideal location, there's off-street parking in the driveway.brbrTHE LIVING AREAS & KITCHEN...brbrSOUTHERN STAR has plenty of space for your group to spread out or come together. The spacious living area has a large flat screen TV, which can be viewed from the plush sectional sofa or from the kitchen/bar area thanks to the open layout of the first floor. On the second floor, you'll find a bonus loft with comfy furniture, perfect for slipping away and getting lost in a good book. brbrThe state-of-the-art kitchen is absolutely stunning, with custom cabinetry and commercial grade appliances including a gas range. You'll find all of the tools and equipment needed to create a gourmet meal from home. The indoor dining area provides seating for four and there's additional seating at the kitchen bar for a casual bite. A powder room is conveniently located in the hall.brbrTHE PORCHES & POOL AREA...brbrThe unique front porch of SOUTHERN STAR is a shady place to people watch, with rockers that make you feel right at home in the South. The back yard is surrounded by a tall fence and lush tropical landscaping, which creates a completely private outdoor setting for your group. Splash around in the private heated pool or take a soak in the jacuzzi. On the side of the house is a real Key West treat: an outdoor shower, perfect for rinsing off after a swim or a day at the beach. There is also a propane BBQ grill and two outdoor dining sets for poolside meals.br brTHE ACCOMMODATIONS...brbrAll bedrooms in this home include flat screen SMART TVs, ceilings fans, and ample storage.brbr** Master Suite: Located on the First Floor with King bed and en suite bathroom.brbr** Second Bedroom: Located on the First Floor with a Queen bed and access to the half bathroom across the hall.brbr** Third Bedroom: Located on the Second Floor with a Queen bed and access to the full bathroom is in the hallway.brbr** Fourth Bedroom: Located on the Second Floor with a King bed and en suite bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen SMART TVs in Living Room & All Bedroomsbr** Gourmet Kitchen with Luxury Appliancesbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbrbrIn addition, this fully stocked home includes, but is not limited to, the amenities on this list:brbr** Gated Backyard with Private Heated Pool & Jacuzzi Spabr** Outdoor Showerbr** Propane BBQ grillbr** Kuerig Coffee Makerbr** Off Street ParkingbrbrOther Notes:brbr** In person welcome when possible, after hours check in availablebr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 8 adultsbr** Small Dogs allowed - Max of 2 dogs allowed and an additional fee of $200 per pet will apply

**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$752.89

Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap around porch, private hot tub along with the shared amenities of Palm Gardens. The condo sits in the back of the building next to the pool. As you enter through the french doors from the wraparound porch, you are welcomed into the living area, with its warm wood walls and furnished with a teal colored sofa (sleeper) to bring in the Caribbean touches Key West is known for.brbrA full kitchen with its granite counters will allow you to cook up a feast or simply make your morning first cup of coffee. The galley style kitchen is complete with refrigerator, stove, microwave and dishwasher for your convenience.brbrThe principal bedroom has a king bed. The adjacent bath has shower stall and stacked washer/dryer.brbrPalm Garden is a small 5 unit compound in two buildings, with a seasonally heated pool and common BBQ area to make the most of your Key West getaway. Located just six blocks from Duval St or the Historic Seaport, you can be in the heart of the action in just minutes by strolling or riding bicycles to get there even faster. Parking is on street parking in the neighborhood, should you be arriving by car in spaces not marked as residential parking.brbrPoolside Hide-Away's location on White Street is close proximity to Sandy's Cafe for your Cuban cheese toast and bucci, just two blocks away. You have to pass Key West Cupcakes to get your Cuban coffee! Fausto's Food palace grocery is just kitty corner from Sandy's to grab anything you need.

Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations

Key West, Florida, United States

Bed

Bath

Sleeps

$637.52

Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. There is a little something for everyone from adventure seekers, to people who just want to get away and enjoy island life, wildlife, sunsets and water activities. From under the boat at any given time you might see many types of fish, stingrays, various crabs, starfish, octopus, lobsters, nurse sharks and even manatee from time to time! From above; view gorgeous sunsets, various sea birds catching their meals and even a military jet formation on occasion. Many great areas to kayak/paddleboard all starting from right off the boat. There are several miles of mangrove trails to view wildlife and fish or just simply get lost in nature. Kayak or paddle board up to Cow Key Marina restaurant as well as Hurricane Hole’s restaurant and grab some lunch.brbrThis houseboat is a 1 bed, 1 - bath with full kitchen/bar hi in appliances including a induction cooktop. and spacious relaxing livingroom. You can also bring your work here and work in peace in this very spacious home office. Also Off the front you have a covered patio with a ceiling fan and the spacious roof top deck with a complete bar top with great views of the bay.brbrThe master bedroom has a king size bed. brbrThe kitchen is A full size with standard size appliances you have the usual comforts of home.brbrThis unit also includes a washer and dryer.brbrNOTE # The houseboat is NOT to be moved from its slip. brIt is a stationary floating cottage.

House Boat

Ocean views!
No regrets

Key West, Florida, United States

Bed

Bath

Sleeps

$166.13

Welcome to our newly remodeled studio apartment, a hidden gem just two blocks from the iconic Duval Street! Nestled within a private gated compound, this chic and cozy space offers the perfect blend of comfort and convenience for your Key West getaway.brbrStep inside and be greeted by a thoughtfully designed studio that seamlessly combines style and functionality. The fully equipped kitchen boasts modern appliances, including a full-sized refrigerator, icemaker, dishwasher, and stove. Prepare your favorite meals with ease, and enjoy them at the dining area or al fresco.brbrThe bathroom is brand new, featuring contemporary fixtures and a refreshing ambiance. A washer and dryer are conveniently tucked away in the unit, making longer stays a breeze. The walk-in closet provides ample storage space for your belongings, keeping the living area clutter-free.brbrFor a restful night's sleep, choose between the comfortable Murphy queen bed on the main floor or ascend to the queen loft bed for a cozy elevated retreat. The flexibility of these sleeping arrangements makes the studio perfect for solo travelers, couples, or hosting friends.brbrMurphy queen bed and loft queen bedbrFully equipped kitchenbrFull-sized refrigerator, icemaker, dishwasher, and stovebrNew bathroom with modern fixturesbrWasher and dryer in-unitbrWalk-in closetbrTwo TVs for entertainmentbrDedicated work spacebrHigh-speed internet includedbrbrWe know your furry friends are a part of the family, so feel free to bring them along! Our studio is pet-friendly, and we've created a welcoming environment for your four-legged companions.brbrSituated just two blocks from the vibrant Duval Street, you're in the heart of the action. Explore the lively atmosphere, world-class dining, and vibrant nightlife that Key West is renowned for. With a private gated compound, you can enjoy tranquility while being moments away from the city's energy.brbrBook your stay now and experience the best of Key West living in our recently remodeled studio – your home away from home!brbrOutdoor camera monitors walkway.

Apartment

Moongate, a Stylish Studio Retreat near Duval, Pet-Friendly, Gated and Private

Key West, Florida, United States

Bed

Bath

Sleeps

$742.5

Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrSet along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life.brbrThis ultra-spacious, ultra-plush two bedroom at Hyatt Windward Pointe features a master bedroom with a king bed and master bath outfitted with a walk-in shower and spa tub, and the guest bedroom with a queen bed. Enjoy the convenience of having a full kitchen, dining area, living room, TV, fully-furnished balcony and complimentary Wi-Fi access!brbrBask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, grab a snack at Abbey Road poolside sandwich and snack bar or get your blood pumping at the fitness center at site resort Hyatt Key West Resort & Spa.brbrComplimentary self-parking is available at the resort. No recreational vehicle parking is permitted. No valet parking is available. Tesla and electric car charging stations are available. Boat and trailer parking is available at $25 plus tax per night and must be booked in advance by calling the front desk.br brbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!

Key West, Florida, United States

Bed

Bath

Sleeps

$752.63

Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to Sunset Pier, explore local beaches, and unravel history at Key West Shipwreck Treasure Museum.brbrStylish, pet-friendly, and amazing decor is what awaits you. This boutique hotel offers you a great stay in the heart of the city, and a chance to unwind. You are welcome to enjoy our outdoor pool, serene cottages, and spacious unit with tropical garden views. Enjoy cozy Turkish robes, a complimentary breakfast, and afternoon tea. Close to Hemingway's home, sunset pier, and beaches, our location ensures a memorable and convenient stay.brbrPLEASE NOTE:brThis listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.brbr- The property requires a Damage Deposit of $50/night/unit on the credit/debit card provided. The deposit is required for each unit and is refunded in full upon check out upon successful inspection.brbr- Early check-in is subject to availability upon arrival.brbr- Following property rules, the minimum age required for check-in is 21 years old.brbr- Upon arrival, a mandatory resort fee of USD 45/night/unit plus tax will be collected, this is not included in the daily rate. brbrWe're delighted you're considering RoomPick’s curated selection of boutique hotels, condo hotels, and resorts worldwide. This room comes with:brbrTHE UNITbrbrThis 200 sq ft King Patio features:br- 1 King bedbr- Flat-screen HDTVbr- Patiobr- Daily housekeepingbr- All linens, towels, and bathroom essentials are provided.brbrTHE PROPERTYbrbrOur charming property provides the following on-site amenities:br- Front Desk (until 6pm) and Securitybr- Outdoor Poolbr- Complimentary Continental Breakfastbr- Concierge Servicesbr- Yoga Matsbr- Merlin's Afternoon Teabr- Complimentary WiFibrbrPARKING brLimited on-site parking is available for USD 30 per day. Advance reservation is required, as parking slots are subject to availability. brbrPET POLICY: Pets are welcome with an additional charge of USD 50.00 per night with no restrictions on size or breedbrbrPlease ensure you have a valid ID for check-in, as it is mandatory for entry.

Hotel

Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier

Key West, Florida, United States

1

Bed

1

Bath