Vacation Rentals By Owner In Siesta Key, FL

Summary:brbrQuaint 1 bedroom bungalow with Murphy bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, French doors open to a private brick patio. 2 Smart TVs (43-inch in living room and 32-nch in bedroom). Kitchen offers a mini convection oven w/ burners above oven, microwave and toaster. Additional hot plate burners in cupboard for total of 4 burners. High speed internet. Located in Village 1 block from restaurants and shops. Small dog allowed$300brbrbrbrOther Things to Note:brbrMust be 25 years old or older to book.

5239 Avenida Navarra in Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$384.52

Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo br2 bedrooms / 2 bathroomsbrNinth Floor Condo with balcony overlooks North-Western Siesta Key- Gulf Views!brFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- 4 Chairs, Umbrella, Beach CartbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbrbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Gorgeous 2bd condo near the beach (AN1079)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$388.36

Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo on Siesta Key br2 Bedrooms / 2 BathroomsbrEighth Floor Condo with Balcony overlooking North-Western Siesta KeybrFully equipped Kitchen with Seating for 4 at the Dining TablebrBeach Supplies include - 4 Beach Chairs, Beach Towels, Beach Umbrella, Cooler & Beach CartbrCommunity Pool- Largest pool on the Key!brGated Community and Parking includedbrSiesta Key Trolley- Free pickup in front of the Resort entrancebrPrivate Beach access to Crescent Beach across the street!brbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Lovely 2bd condo close to the beach (AN1145)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$486.5

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrWelcome to Lulu's Key House Leatherback!brbrThe condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away.brNew furnishing!brbrLOCATION HIGHLIGHTS:br- Just a couple of blocks to Siesta Key Beach and Gulf watersbr- Steps to restaurants, shops, coffee houses, and nightlifebr- No car needed to enjoy the village and beachbrbrPROPERTY FEATURES:br- 2 bedroom/ 2 bathroom ground floor unit (851 sq ft)br- Crown molding, solid stone counters, stainless kitchen appliances, porcelain wide plank tiles, plantation shuttersbr- Shared stackable washers/dryers in buildingbr- Heated communal pool on-site with loungers and umbrella, outdoor showerbr- Front porch with swingbrbrLIVING ROOM:br- Large Smart TV with cable and Frontier servicebr- Free WiFi and USB charging portbr- Spacious seating area for family and guestsbrbrKITCHEN AND DINING:br- Modern kitchen with quartz countertops and tiled floorsbr- New stainless steel appliances including dishwasher and microwavebr- Fully stocked with dishes, utensils, and small appliancesbr- Dining table seats 6brbrBEDROOMS AND BATHROOMS:br- Master bedroom: king bed with memory foam mattresses, flat screen and closet spacebr- Master ensuite bathroom: vanity and walk-in showerbr- Guest bedroom: king bed with TV and cablebr- Guest bathroom: vanity, tub/shower combobrbrEXTRA PERKS:br- Complimentary beach items provided: beach chairs, beach cart, umbrella, and beach towelsbrbrLOCAL FAVORITES:br- Steps to Siesta Key Village for shopping, dining, bars, and coffee shopsbr- Short walk to Siesta Key Beach and Gulf watersbr- Perfect location for a car-free vacationbrbrIMPORTANT INFO:br- Two assigned parking spots marked “Leatherback”br- Option to rent multiple units or the entire 4-plex for private group staybr- Confirm approval for special vehicles including boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized/commercial vehiclesbr- Flexible dates of staybrbrDON'T WAIT - MAKE THIS TRIP YOURS!brWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

$185 Free Activities Daily, LuLu's Leatherback Near Beach/Village, Heated Pool, Beach Gear Included

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$420.91

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrWelcome to Lulu's Key House Kemp Ridley!brbrThis oasis on Siesta Key is just paradise. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and night life are steps away. The beach and the crystal clear waters of the Gulf of Mexico is also about a 5 minute walk. You don't need a car. Your vacation destination is here!brbrLOCATION HIGHLIGHTS:br- Ground-level unit in Siesta Key Village – Steps to dining, shops, coffee houses, and nightlifebr- Just a 5-minute walk to Siesta Key Beach and the Gulf of Mexicobr- No car needed to enjoy restaurants, beach, and village attractionsbr- Quiet back location within 4-unit complexbrbrPROPERTY FEATURES:br- 1 bedroom/ 1 bathroom ground floor condo (640 sq ft)br- Heated communal pool, 5 ft at deepest with outdoor showerbr- Crown molding, quartz counters, stainless kitchen appliances, porcelain plank tile, plantation shuttersbr- Shared stackable washers/dryers on-site at no chargebrbrLIVING ROOM:br- Large Smart TV with cable and Frontier TV servicebr- Free WiFi and USB charging portbr- Queen sofa sleeper for extra guestsbrbrKITCHEN AND DINING:br- Fully stocked modern kitchen with stainless steel appliances, dishes, utensils, and cookwarebr- Quartz countertops and tiled floorsbr- Dining area for 4brbrBEDROOMS AND BATHROOMS:br- King bed with comfortable mattressbr- Wall-mounted TV with cable in bedroombr- Bathroom with walk-in shower and glass doorsbrbrEXTRA PERKS:br- Complimentary beach items provided: beach chairs, umbrella, cart, and beach towelsbrbrLOCAL FAVORITES:br- Steps to Siesta Key Village for shopping, restaurants, bars, and coffee shopsbr- Short walk to Siesta Key Beach and Gulf watersbrbrIMPORTANT INFO:br- 1 assigned parking space labeled “Kemp Ridley”br- No smoking or pets allowedbr- Option to rent multiple units or the entire 4-plex for a private group staybr- Confirm approval for special vehicles including boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized/commercial vehiclesbr- Flexible dates of staybrbrYOUR VACATION STARTS THE MOMENT YOU BOOK AT LULU'S KEY HOUSE!brWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$327.8

Plan the perfect beach vacation at this Florida vacation rental just steps away from the ocean. This 1-bathroom studio in Siesta Key, Florida, is surrounded by lush landscaping and palm trees to make you feel like you’re in paradise as soon as you arrive. Enjoy a fully equipped interior, shared pool, and provided beach gear so you can pack up and head to the beach whenever you want. Sunshine-loving families and friends can spend the day on the shore followed by an evening in Siesta Key Village!brbr-- THE PROPERTY --brbrBeach Cooler & Towels | Private Balcony | 0.3 Mi to Public BeachbrbrStudio: Queen Bed, Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play brbrOUTDOOR LIVING: (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsbrSTUDIO LIVING: Smart TV, beachy interior, 4-person dining tablebrKITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, dishware & flatware, ice maker, microwave, toaster, blenderbrGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, central air conditioning, shared laundry machines, hair dryer, iron/board, trash bags & paper towelsbrFAQ: 1 exterior security camera (facing out), stairs required for access brPARKING: Shared parking lot (1 vehicle) brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, both with separate nightly rates: a 2-bedroom for 6 guests and a studio for 3 guests. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrLOCAL BEACHES: Sarasota Beach (0.3 miles), Crescent Beach (2 miles), Bayfront Park (6 miles)brSTATE PARKS: Oscar Scherer State Park (11 miles), Myakka River State Park (17 miles)brEXPLORE THE AREA: Siesta Key Village (0.1 miles), Marie Selby Botanical Gardens (5 miles), Sarasota Jungle Gardens (9 miles), Mote Marine Laboratory & Aquarium (10 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (10 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are other bookable rentals on-site; other travelers may be present and share the driveway and some outdoor amenitiesbr- NOTE: Your safety matters. This property features 1 exterior security camera. This camera is located on the front entrance of the main house and faces the parking area. It actively records video and audio and will be turned on during your staybr- NOTE: This property is located on the second floor and requires stairs to access

Siesta Key Dream Inn Rental - Close to Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$305.18

Your next vacation awaits in Siesta Key, Florida! This beachy 1-bath studio is the ideal Florida vacation rental for you and your significant other. Spend your days soaking up the sun on the beach nearby, hanging out by the pool area with a cold drink, or visiting Siesta Key Village where you’ll find shopping, dining, and bars. There’s also plenty to do nearby when you’ve had enough sun, including museums and botanical gardens! You’ll never be bored when you visit this Siesta Key beach rental.brbr-- THE PROPERTY --brbrSarasota VR Certification: CND6804981 | Beach Cooler & Towels | Shared Heated Pool | 1 Block to Siesta Key Village brbrStudio: Queen Bed, Twin Sleeper Sofa brbrOUTDOOR LIVING (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsbrSTUDIO LIVING: Smart TV, beachy interior, 2-person dining table, patio w/ outdoor seating brKITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, dishware & flatware, ice maker, microwave, toaster, blenderbrGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, central heating & air conditioning, shared laundry machines, hair dryer, iron/board, trash bags & paper towelsbrFAQ: 1 exterior security camera (facing out), step-free access brPARKING: Shared parking lot (1 vehicle) brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, both with separate nightly rates: a 2-bedroom for 6 guests and a studio for 4 guests. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrLOCAL BEACHES: Sarasota Beach (0.3 miles), Crescent Beach (2 miles), Bayfront Park (6 miles)brSTATE PARKS: Oscar Scherer State Park (11 miles), Myakka River State Park (17 miles)brEXPLORE THE AREA: Siesta Key Village (0.1 miles), Marie Selby Botanical Gardens (5 miles), Sarasota Jungle Gardens (9 miles), Mote Marine Laboratory & Aquarium (10 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (10 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are other bookable rentals on-site; other travelers may be present and share the driveway and some outdoor amenitiesbr- NOTE: Your safety matters. This property features 1 exterior security camera. This camera is located on the front entrance of the main house and faces the parking area. It actively records video and audio and will be turned on during your stay

Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$271.46

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo - Corner Unitbr2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Southern and Western Siesta KeybrThird Floor Condo overlooks the canal and Gulf of MexicobrFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- Chairs, Umbrella, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbr25-year minimum age to rent restrictionbrbrBEDROOMS (Third Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) / Balcony AccessbrBedroom 2: Two Double Beds (Attached Bathroom) / Balcony AccessbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 3rd Floor 2 Bedroom Condo South/West Balconies

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$1367.75

Summary:brbrThis stunning six-bedroom, four-bath home on Siesta Key is an absolute must-see! Perfectly situated just steps from Siesta Key Village, you’ll have the island’s best shopping, dining, and entertainment right at your doorstep. Plus, it’s only minutes away from the powdery white sands of world-famous Siesta Key Beach—making this the ultimate coastal retreat for relaxation and fun in the sun.Kick back and relax in this calm, stylish space.brbrbrbrThe Space:brbr☀️ Southern Exposure | 2 Homes from Beach • Heated Pool ️brbr 91 Avenida Veneccia, Siesta KeybrbrbrbrWelcome to Southern Exposure, your coastal escape just two homes from the beach and steps from vibrant Siesta Key Village ️ With six bedrooms, four bathrooms, and a private heated pool, this bright and stylish retreat is perfect for families, friends, and sun-seekers looking to experience the best of island living.brbrbrbrSpend your mornings strolling to the beach for powder-soft white sand and turquoise Gulf waters . Walk to the Village for coffee, boutique shopping, fresh seafood, and live music—then come home to your private backyard paradise.brbrbrbrInside, the open-concept layout is filled with natural light and crisp coastal charm. The airy white interior, cozy living room with a white brick faux fireplace, and thoughtfully updated finishes create a warm and welcoming space. The kitchen features granite countertops, stainless steel appliances, and bar seating—perfect for gathering after beach days ️✨brbrbrbrStep outside to your private oasis where you’ll find a sparkling heated pool with in-water sun shelf, lush turf yard, lounge chairs, and an outdoor dining area with grill—ideal for soaking up the Florida sunshine and enjoying laid-back BBQ evenings ☀️brbrbrbrPet-friendly (dogs with approval & fee), so your furry family members can enjoy island life too brbrbrbr✨ Highlightsbrbr• ️ Only 2 homes from the beachbrbr• Steps to Siesta Key Villagebrbr• Private heated pool with sun shelfbrbr• Tropical backyard with turf yardbrbr• Outdoor dining area & BBQ grillbrbr• Dog-friendly (approval & fee required)brbr• ️ 6 Bedrooms / 4 Bathroomsbrbr• ☀️ Bright open-concept coastal designbrbrbrbr ️ BedroomsbrbrMain Level:brbr• Bedroom 1 – Twin over Full bunk bedbrbr• Bedroom 2 – Queen bedbrbr• Bedroom 3 – King bedbrbrbrbrUpper Level:brbr• Bedroom 4 – King bedbrbr• Bedroom 5 – King bedbrbr• Bedroom 6 – Two Full bedsbrbrbrbrPerfect layout for multiple families or large groups traveling together.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

Southern Exposure~2 Homes from Beach! Heated Pool!

Siesta Key, Florida, United States

5

Bed

Bath

13

Sleeps

$267.89

Aloha Kai #43brbrTime for Some Beach Time!br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #43. This charming beach villa is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Fresh and inviting with colorful coastal comfort, Aloha Kai #43 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: br1 Bedroom: brMaster Suite: King-size bed and Smart TV brAdditional Sleep: Queen-size sleep sofa in the living areabrTop Features: brSleeps 4 brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation. brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort. brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun. brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #43 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this villa offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #43 today and create memories that will last a lifetime! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brbrDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Sun, Sand, and Relaxation! - Aloha Kai #43 - Roelens

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$667.73

Aloha Kai #34 & #55 (Combined Villas) br(Across the street from each other) br brA Siesta Key Beachside Bliss Awaits! br brStep into the tropical embrace of Aloha Kai #34 & #55, where the rhythmic charm of Siesta Key and a short stroll to Crescent Beach create a perfect escape. This combined villa duo transforms two homes into a seamless paradise, blending sunlit serenity with island adventure. Aloha Kai #34 & #55 invites you to shed your worries, sip coffee on your private patios, and dive into a world of relaxation—book your island haven today! Here's what makes this home so special:brbrBedding Arrangement: brbrAloha Kai #34: br1 Bedroom: brMaster Suite: Queen-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brAloha Kai #55: br1 Bedroom: brMaster Suite: King-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brTop Features: brSleeps 8 brLargest Pools on Siesta Key: Plunge into the expansive, sparkling pools surrounded by large lounging decks with plenty of lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access Points: Just a short walk to the powdery white sands of Crescent Beach, rated #1 in the U.S., with shaded pavilions and lounge chairs for your comfort. brFront Patio/Sunroom: Sip morning coffee or unwind with a book in the bright, enclosed sunroom. brCommunity Amenity Sets: Enjoy shuffleboard, ping pong, and poolside community rooms, plus complimentary beach toys and floats for endless seaside fun. brPerfect Home Base Location: Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for island exploration, with activities for all ages and nature lovers. brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #34 & #55 offers easy access to Crescent Beach, famed for its dazzling quartz sand and emerald waters. Whether you're strolling the 3-mile shoreline, lounging under a shaded pavilion, or savoring breathtaking Gulf sunsets, this villa pair delivers tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be effortless and unforgettable. Book your Siesta Key escape at Aloha Kai #34 & #55 today! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brbrDISCLAIMERS: br10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits. brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property. Every Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens

Siesta Key, Florida, United States

Bed

Bath

8

Sleeps

$376.91

Leona Breeze by Tropical Sands Accommodationsbr369 Avenida Leona, Siesta Key, FloridabrbrWelcome to Leona Breeze, the perfect home for long-term renters seeking a relaxed, comfortable stay on Siesta Key. Designed for extended stays, this two-story residence offers four bedrooms and two and a half bathrooms, providing the ideal backdrop for families, professionals, or groups looking to settle into a peaceful, Florida retreat. Located at the end of a quiet cul-de-sac, the home offers privacy and stunning canal-front views, just five minutes from Siesta Key Village’s shopping and dining, and a 13-minute walk to the renowned #1 beach in America.brbrHighlightsbr• 30-night minimum staybr• Dog friendly with approval and additional feebr• 13-minute walk to the beachbr• Canal frontbr• Large kitchenbr• Snowbird friendlybr• Water viewsbr• Two living areasbr• Laundry roombr• BBQ grillbrbrOutside, enjoy the tranquil, private backyard, perfect for unwinding or hosting friends. Sip morning coffee beside the canal or gather in the evening around the pool, your personal tropical oasis. Fish from your own backyard or simply relax in your serene surroundings.brbrInside, terrazzo floors and water views create a welcoming, serene atmosphere. The open-concept kitchen features stainless steel appliances and a large island, perfect for meal prep or casual entertaining. With two living areas, everyone has space to relax and unwind.brbrThe four bedrooms are thoughtfully furnished for comfort. The primary suite includes a queen bed and an ensuite bathroom with a walk-in shower. The other three bedrooms include three queen beds and a full bed, sharing a spacious hallway bathroom with a shower/tub combo, and a half bath rounds out the first floor.brbrRoom Detailsbr-Primary Bedroom, 2nd floor: Queen bed and ensuite bathroom with walk-in showerbr-Second Bedroom, 2nd floor: Queen bedbr-Third Bedroom, 2nd floor: Queen bedbr-Fourth Bedroom, 2nd floor: Full bedbrbrIf you’re searching for a laid-back, long-term Florida escape, Leona Breeze offers the comfort, privacy, and slice of paradise you’ve been dreaming of. Book now and settle into your ultimate Siesta Key retreat!brbr-brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Tropical Sands Accommodations Rental Policies for full details.brbrbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Leona Breeze: Long Term Perfection!

Siesta Key, Florida, United States

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Sleeps

$698.64

pbr/pbrbrpRelax & Recharge at Siesta Key Beach/pbrbrp(2 beach cruiser bikesadditional $35 each per stay)/pbrbrbrbrpPoolside studio villa with a full kitchen, solid surface countertops & stainless steel appliances. Queen size Murphy bed and queen-size sofa bed./pbrbrpRecently updated kitchen, bathroom, and a complete living area./pbrbrpIt overlooks 1 of 3 pools/pbrbrpEnjoy the morning sun with your coffee on the patio/pbrbrpDirect private beach access with complimentary lounge chairs located on the beach./pbrbrpoutdoor showers by the beach access/pbrbrpAll kitchen items to cook and community bbq located by the beach access./pbrbrpLaundry Facilities on Property covered designated Parking/pbrbrp Shuffleboard /pbrbrbrbrbrbrp3 Community Heated Pools Fully Equipped Kitchen Internet Access Heat and Air Conditioning /pbrbrpNo Pets Allowed /pbrbrpNo Smoking Outdoor Patio Carport /pbrbrpOcean Nearby /pbrbrpBeach Access/pbrbrpOnsite coin laundry./pbrbrpCommunity pool/pbrbrpI will be available by air bnb messenger and have a local contact if needed./pbrbrpThis will be a self check in and check out with a key in lockbox./pbrbrpAMERICAS #1 BEACH enjoy white quartz sand and warm Gulf of Mexico water./pbrbrpOpen/pbrbrpAir trolley -runs every 20 minutes to the village area/pbrbrpSecurity cameras on exterior of unit/p

[Beach Elements] pool view withprivate beach access

Siesta Key, Florida, United States

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Bath

Sleeps

$418.44

Welcome to Crescent Arms Villa 17brTHIS UNIT HAS BEED COMPLETLY REMODELED !!!!!!!! IT is a must see unit. This open-concept, stand-alone villa is continuously updated by active owners. All rooms have lots of natural light and are furnished with beach style furniture and decor to add to your vacation experience. Villa 17 offers 2 King Suite bedrooms, is located next to the pool and is about 100 steps to the beach; the best of both worlds! We are just a 1/4 mile walk to grocery, restaurants, and bars. We are about a 1 mile walk to the public beach (Siesta Beach) and a 1/4 mile walk to Point of Rocks.brThe unit features:br3 flat screen TV's (55in the living room) and has an outdoor patio set and private grill. The kitchen has stainless steel appliances and the attached garage offers a washer and dryer. Come enjoy and start making lasting memories with your family and friends. Your vacation can't get any easier. Book early so you don't miss this opportunity and don't forget to rebook if you enjoyed your stay.brFeatures/Amenities:brPrivate Beach (Crescent) Heated Community Pool Beach Towels Lounge Chairs at pool Beach Chairs at beach Floats and sand/pool toys Air Conditioning Cable TVs ( 3 ) Wireless Internet in unit Ceiling Fans Community Gas Grills Plus a Private LP (propane) Grill Private outdoor table & chairs Fully Equipped Kitchen Coffee Maker Toaster Dishwasher Refrigerator Electric Stove Microwave Attached Garage Washer & Dryer in Unit Hair Dryers Iron/Ironing Board Designated Parking No Smoking No Pets brCrescent Arms features: Easy access on and off the Island! Fully Furnished, Gated Condominiums 2 Bedrooms/2 Baths Private Wireless Internet in Unit Private Beach Access with Chairs Steps to the beach 1-Week, Saturday to Saturday, Minimum Required Stay

Villa

Crescent Arms Vacation Rentals Villa 17 Siesta Key Florida

Siesta Key, Florida, United States

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Sleeps

$351.73

FULL BAY VIEWS FROM THIS 1ST FLOOR UNIT. brYOU CAN’T GET ANY CLOSER TO THE BAY THAN THIS. brbrSit on your screened in Lanai while you watch the boats and wildlife. The versatile layout boasts one spacious bedroom, and a smaller guest bedroom. Washer and dryer in unit. Newer Hurricane windows & sliding door. brbrIn addition to beautiful views & fabulous location the Amenities include a community fishing pier with great views up and down the inter-coastal waterway, picnic and grilling area, clubhouse, covered parking, tennis courts, heated pool. A short walk puts you on the sugar-fine quartz white sands of the World-Famous Siesta Key Beach or jump on the trolley to all the other attractions Siesta offers. brbrIt's time to create memories that will last a lifetime in your own little piece of paradise. brThis condo is Florida resort-style living at its finest!

Siesta Key Direct Water Views - A

Siesta Key, Florida, United States

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Sleeps

$726.43

This stunning property offers a waterfront oasis, a short stroll away from the village. With 3 bedrooms and 3 full bathrooms, including 2 master suites and a private deck, this home is designed for ultimate comfort and relaxation. The split plan layout provides guests with their own separate areas to unwind. You'll love the impressive patio area, which leads to an oversized saltwater pool surrounded by Travertine pavers - perfect for soaking up the sun and enjoying a peaceful afternoon.

Paradise Retreat

Siesta Key, Florida, United States

3

Bed

3

Bath

6

Sleeps

$160.62

Harbor Towers is known as a tropical Bayside community with the most stunning marina on Siesta Key. It's located directly on the Gulf Coast Intracoastal waterway with some of the most captivating landscapes on the island. Harbor Towers is secure full facilities complex with a relaxing seawall and seating area near the marina where you can fish, watch the sunrise, and see dolphins jumping.brHarbor Towers is located just a short distance from the Siesta Key Village where you can shop, visit bars/restaurants, listen to live music, and enjoy a fantastic night out. brHarbor Towers has three Har-Tru lighted clay tennis courts, a heated community pool, a separate baby pool, four grilling stations with tables and chairs, a state of art fitness facility equipped with treadmills, elliptical machines, weight machines, free weights, and two sauna rooms. A social room is also available upon reservation with a fully equipped kitchen, tables, and a wide-screen TV. The grilling stations are located on an expansive poolside patio area, with ample tables and seating to enjoy your meals. The complex is friendly and frequently hosts events for residents and guests. Take a stroll around the property and stop by the Island Gazebo near the seawall overlooking the bay. Relax in the shade and you may spot some dolphins or manatees.brThis unit (405) is located on the East corridor on the fourth floor, it faces east/south with plenty of sunlight throughout the year.brThere are two bedrooms in this unit, each located on the opposite sides of the living/dining room. Each bedroom has its own updated full bathrooms, King Size beds, and flat-screen TVs. You can view the water from both bedrooms so you can wake up to glimpses of sparkling water in the morning. The master bedroom features a dresser, a sitting area, and a walk-in closet. The second bedroom offers a workstation with spacious storage and a comfortable office chair. brThe living room is bright and sunny, with unobstructed views from the 4th floor. The room is decorated in cheerful and welcoming colors with a couch for relaxation, armchairs, and a flat-screen TV. You can enjoy coffee every morning or have a drink in the evening on the shady screened-in balcony with a beautiful Intracoastal view! The dining table can comfortably sit up to four or five.brThe completely renovated kitchen includes stainless appliances and granite countertops, new cabinetry, dishes, cookware, and stemware. The coffeemaker and air fryer will help you prepare your favorite foods easily.brThere is free WIFI throughout the unit. Four beach chairs, a beach umbrella, and fishing rods are available.brThis unit comes with a coveted parking spot (N30) to keep your car cool in the summer heat and is conveniently located close to the entrance to the building.

White Sand Beach Retreat. only 10 minutes walk to Siesta Kay Beach

Siesta Key, Florida, United States

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$358.65

Gulf-Front Corner Condo | Chic 2BR Retreat with Sunset Views & Beach AccessbrbrWelcome to Unit 201, your private beach retreat on beautiful Siesta Key! Perfectly positioned on the second floor with an exclusive corner location, this 2-bedroom, 2-bathroom condo offers 1,210 sq ft of bright, breezy luxury—just steps from the soft white sands of the Gulf of Mexico.brbrStart your mornings with coffee and end your evenings with a front-row seat to breathtaking sunsets, all from the comfort of your coastal-chic getaway. With extra windows that invite in natural light and sea air, this unit radiates a laid-back beach vibe with upscale touches throughout. Stylish, updated fixtures ensure your stay is as comfortable as it is elegant.brbrThe master bedroom features two plush queen beds, while the second bedroom offers a king-sized escape, perfect for recharging after a day in the sun. Enjoy your favorite shows on one of three flat-screen TVs, and make use of the fully stocked kitchen to whip up everything from quick snacks to full meals. This condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon.brbrStep outside to enjoy Crescent Royale’s amenities: a heated pool, shuffleboard courts, BBQ grills, and direct beach access just beyond your doorstep. Whether you're swimming, sunbathing, or simply strolling the shoreline, you'll feel like you've found paradise.brbrTake a short walk or hop on the free trolley to explore Siesta Key Village, where you’ll find lively restaurants, boutique shops, and entertainment. Plus, an onsite management team is always available to help make your stay seamless.brbrUnit 201 is more than a vacation rental—it’s a front-row seat to Gulf Coast beauty. Book now and start making your Siesta Key memories today!

Siesta Key Beach 2BR 2 BA Corner Condo XL Lanai and Ocean Views

Siesta Key, Florida, United States

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Bath

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$382.38

Prepare to feel regal as you step into our luxurious silver-rated condo, situated in the heart of Florida's tropical paradise. Imagine waking up to the serene sound of waves crashing onto the shore, sipping coffee while admiring the picturesque blue ocean from your window. Our condo is the perfect place to live out your dream beach vacation.brbrWith two bedrooms, two full baths, and a spacious 1220 square feet of living space, you'll have ample room to relax and unwind. The master bedroom features a plush king-sized bed, while the second bedroom offers two twin beds that can be combined to form a king bed. You won't need to worry about packing cumbersome beach gear as we've got you covered with all the essentials, including beach towels, linens, chairs, and even an umbrella!brbrThe fully equipped kitchen provides an ideal setting for preparing family meals or romantic dinners, while the screened lanai offers a picturesque location to enjoy your meal with breathtaking ocean views. After a day of soaking up the sun on the top-ranked US beach (just 100 steps away!), you can relax by the heated pool or fire up the gas grill for a cookout.brbrFor those who enjoy an active lifestyle, our resort-style complex features an exercise gym to help you stay in shape while on vacation. And when you're ready to explore, you're only a short walk away from the Village's restaurants and nightlife.brbrOur onsite management team is committed to providing excellent service to cater to your every need, ensuring your vacation is nothing short of paradise. So, pack your beach essentials and come immerse yourself in the ultimate beach vacation at our opulent Florida condo!

Gulf Views 2 Bed 2 Bath at Siesta Key Beach 100 Steps to the Sand

Siesta Key, Florida, United States

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