Home Vacation Rentals By Owner In Fairfield, CT

Showing 20 Of 83 Vacation Rentals
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Exceptional(27)

$486.4

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Private Vacation Home

Cozy Cottage with Fire Pit, near Beach

Fairfield, Connecticut, United States

Summary:brbrEscape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities for an unforgettable stay.brbrbrbrThe Space:brbrWelcome to our sun-drenched and stylish cottage, thoughtfully curated for connection and relaxation. The home features central air conditioning and fast wireless internet throughout.brbrbrbrLiving & Dining:brbr Open-concept living area with ample natural light and a cozy wood-burning fireplace.brbr Adjacent dining room with seating for eight, stylish décor, and its own fireplace.brbrbrbrKitchen:brbr Fully equipped kitchen with charming mint green cabinets, stocked with pots, pans, glassware and dishes.brbr Dedicated coffee and tea bar featuring a Keurig with a selection of coffee pods, teas, creamers, and sweeteners.brbrbrbrBedrooms & Workspace:brbrAll bedrooms feature Green Tea memory foam mattresses, hotel-quality linens, blackout shades, and Roku-enabled smart TVs.brbr Bedroom 1 (First Floor): One king-sized bed.brbr Bedroom 2 (Second Floor): One queen-sized bed.brbr Bedroom 3 (Second Floor): Two double beds.brbr brbrA dedicated workspace is available for those needing to stay connected.brbrbrbrBathrooms:brbrTwo luxurious bathrooms are stocked with plush towels and complimentary shampoo, conditioner, and body wash.brbr Bathroom 1 (First Floor): Features a deep soaking tub and a rain head shower system.brbr Bathroom 2: (First Floor): Offers a modern walk-in shower with a 10 rain head.brbrbrbrOutdoor Space:brbr Private patio with an eight-person dining table. BBQ grill for outdoor cooking.brbr Comfortable seating around a gas fire pit.brbr Outdoor games provided, including Giant Jenga, and horseshoes.brbrbrbrFamily-Friendly Amenities:brbr Pack 'n Playbrbr Booster chair with tray tablebrbr Baby bath brbr Children's books and toysbrbr Safety gatesbrbr Fireplace guardsbrbrbrbrConveniences:brbr High-end washer and dryer available for guest use.brbrbrbrBeach Essentials: Plan a perfect beach day with essentials ready and waiting. We provide beach towels, six beach chairs, and an umbrella. Spend less time packing and more time swimming, strolling, and soaking up the sun.brbrbrbrGuest Access:brbrGuests will have private and exclusive access to the entire home, including the private patio and all listed amenities. Please make yourself at home!brbrbrbrThe Neighborhood:brbrFairfield is a charming coastal town located in Fairfield County, Connecticut. The town is situated on Long Island Sound, offering beautiful views of the water and easy access to beaches and parks. Fairfield is a family-friendly community with a lively downtown area, and plenty of recreational opportunities.brbrbrbrDowntown Fairfield is a hub of activity, with a variety of shops, restaurants, and entertainment options. The area is pedestrian-friendly and features historic buildings, tree-lined streets, and a bustling nightlife. The town also has several parks and open spaces, including Lake Mohegan, the Connecticut Audubon Society Birdcraft Museum and Sanctuary, and the Southport Beach and Harbor.brbrbrbrThe town has a strong sense of community, with many events and activities throughout the year, including the Fairfield County Irish Festival, the Fairfield Sidewalk Sale and Street Fair, and the Fairfield Christmas Tree Festival.brbrbrbrOverall, Fairfield is a welcoming and vibrant town with a strong sense of community, beautiful natural surroundings, and plenty of amenities and attractions for residents and visitors alike.brbrbrbrGetting Around:brbrThere are several ways to get around the area. Here are some transportation options you might find helpful:brbrbrbr1. Car rental: Many visitors to Fairfield opt to rent a car to get around town and explore the surrounding areas. There are several car rental companies in the area, including Enterprise, Hertz, and Avis.brbrbrbr2. Taxi and ride-sharing services: Taxis and ride-sharing services like Uber and Lyft are also available in Fairfield. Guests can easily request a ride through the app and be picked up at their location.brbrbrbr3. Public transportation: Fairfield is served by the Greater Bridgeport Transit Authority (GBTA), which offers bus service throughout the town and to neighboring towns. The GBTA also operates a shuttle service that connects Fairfield's train stations to the town center.brbrbrbr4. Biking and walking: Fairfield is a pedestrian and bike-friendly town, with many sidewalks and bike lanes throughout the area. Guests may choose to explore the town on foot or by renting a bike.brbrbrbr5. Train: The Metro-North Railroad provides train service to Fairfield, with multiple stops in the area. Guests can take the train to nearby towns like Bridgeport, Stamford, and New York City.brbrbrbrOther Things to Note:brbrPlease be mindful that our home is located in a quiet, residential neighborhood. We have a wonderful relationship with our neighbors and kindly ask for your help in maintaining a peaceful environment for everyone. Your consideration is greatly appreciated.brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self-check-in process. While we will not be present during your stay, we are always available and happy to assist with any questions or recommendations.
Bed 3

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Bath 2

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Sleep 8

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Exceptional(23)

$1744.17

/ Nightly
Private Vacation Home

Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Fairfield, Connecticut, United States

Location, Location, Location. *Completely renovated Spring 2023*brbrCovered in ivy, this beautiful 6 bedroom/5 bath English Tudor on the historic Old Post Road is only 1 block to downtown Fairfield with great restaurants, theatre, concerts, shopping and a Metro North station (1 hour to NYC). Or walk 4 blocks the other way to Fairfield's private Penfield Beach with pavilion, lockers/showers and concessions.brbrProminently sited on Fairfield's premiere street of stately homes with estate grounds of lush lawns, perennial gardens and specimen trees showcasing a very private heated pool with lovely chaise lounges, umbrellas, gas fire table with recliners and bar dining table . br brThe property also features a story book Guest Cottage with kitchenette (refrigerator, freezer, dishwasher, convection microwave, Keurig), huge leather sectional, 65 TV, Queen bedroom, washer/dryer and full bath. Enjoy both indoor and outdoor dining for all in this beautiful setting.br brHighlights of the Main House include a designer Kitchen with marble counters, seating island, stainless steel appliances. A classic formal Living Room with new Chesterfield leather couches, piano and wood burning fireplace. Comfortable Family Room with new reclining sofas. Elegant, large Dining Room. Upstairs Library with office. Two King Ensuite bedrooms and three additional bedrooms (2 queen/1 king). Large 3rd floor bunk room with twin beds and futon. 2nd floor Laundry Room. All TVs feature premium cable with Apple TV units and Amazon Fire Sticks. Optimum Fiber (1G) for Wifi/streaming service.
Bed 6

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Bath 4

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Sleep 14

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Exceptional(2)

$356.25

/ Nightly
Apartment

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Fairfield, Connecticut, United States

About this spacebrWelcome to Cherish Suites! Newly renovated 3-bedroom apartment complete with two plush king-size beds and one plush queen bed. A cozy space perfect for families or small events to enjoy in the large yard equipped with a picnic table for lunch and two fire pits perfect for s'mores.brbrThe spacebrNeeding some time with family or just looking for some relaxation Either way, share the moments in our newly renovated 3-bedroom apartment equipped with everything to make your stay pleasant and memorable. The house includes modern amenities such as high-speed Wi-Fi and smart TVs, allowing you to log into your streaming accounts to enjoy all your favorite TV shows and movies.brbrThis apartment is one step away from you calling it your very own home away from home.brbrHigh-Speed Wi-Fi: Stay connected with fast internet.brSmart TVs: Log into your streaming accounts to enjoy all your favorite TV shows and movies.brThree Bedrooms: Comfortable and spacious.brBathroom: Modern and clean.brLiving Room: Relax and unwind.brFully Equipped Kitchen: All the essentials for cooking.brBonus Room (Additional fee)brbrGame Room: Pool table, darts, basketball arcade game, and foosball table.brHome Theater Setup: Couch with a queen pullout foam mattress and four black leather stadium-style seats with a massage feature.brNearby Attractions & ActivitiesbrbrConnecticut's Beardsley Zoo: With over 90 years of history, this zoo is a haven for endangered animals. Enjoy educational exhibits and learn about conservation efforts while having a wild adventure with family and friends.brThe Adventure Park at The Discovery Museum: Explore five acres of thrilling ropes courses and ziplines. Perfect for adventurers of all ages (5+), this park offers a day full of excitement and teamwork.brFairfield Museum and History Center: Dive into the rich history of Fairfield at this engaging museum and library. Established by the Fairfield Historical Society, it's a fantastic place to learn about the past and its impact on the community.brSightseeingbrbrFayerweather Island Light: Enjoy a scenic walk to this historic lighthouse. Explore unique rock carvings and soak in the breathtaking views.brSteel Point: Experience the vibrant mixed-use development at Steelpointe Harbor. With stunning waterfront views, green spaces, and a variety of dining options like Boca Oyster Bar and Uncle Buck’s Fishbowl and Grill, it’s a perfect spot to relax and enjoy the scenery.brLake Mohegan Dog Park: Explore 170.4 acres of open space with hiking trails and a popular swimming area. This fresh water lake is perfect for a summer swim, and the sandy beach is a hit with families.brJennings Beach: With a gentle curve and calm, shallow waters, this beach is ideal for families. Enjoy a picnic and catch a movie screening or a family dance on summer nights.brTop RestaurantsbrbrCraft 260: Relish elevated pub fare and craft draft beer in a stylish, modern-rustic space with a cozy covered patio.brBarcelona Wine Bar: Indulge in a tapas bar inspired by Spain, offering seasonal ingredients and a stellar selection of wines. A must-visit for food and wine enthusiasts.brFrank Pepe Pizzeria Napoletana: Delight in coal-fired pizzas at this iconic local chain. Perfect for a casual, delicious meal.brVeracious Brewing Company: Just 15 minutes away, enjoy a variety of brews in a convivial taproom. From American stout to Belgian-style pale ale, there’s something for every beer lover. Don’t miss the food trucks and live music!brPantanal: Savor a variety of meats at this Brazilian buffet restaurant. A paradise for meat lovers!brGeronimo Tequila Bar and Southwest Grill: Experience chic Southwestern dining with an extensive tequila selection and Mexican-inspired dishes.brEnjoy your stay and make the most of all the wonderful experiences around town!brbrGuest accessbrThis multifamily home offers you full private access to the first floor, making it the perfect choice for your getaway. Whether you're visiting for business or seeking a romantic retreat, this space is tailored to meet your needs.brbrThe whole first-floor apartment and the shared massive yard.brbrAugust Lock System: Secure and private entry.brOutside Lounge: Relax in comfort.brFire Pits: For cozy nights (guests must provide their own supplies).brPicnic Table: Ideal for outdoor meals.brEntertainment System: For your leisure.brAlexa: Smart home convenience.brDesks: For working from home.brSeparate Entrances: For added privacy.brbrOther things to notebrBookings must be made by persons over 21 years of age. Any booking by persons younger will be automatically rejected. If discovered during your event, you agree to be immediately removed from the premises.brParking: All guests must park on Fairchild Ave. to avoid tickets.brFor stays over 14 days, an additional cleaning fee is required.brQuiet Hours: Weekdays 10pm-8am and weekends 11pm-8am. There is a nuisance fee for breaking this rule to ensure all guests have a quiet, comfortable stay.brSecurity Cameras: There are security cameras around the property for your safety.brbrCome ready to have an amazing time!
Bed 3

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Bath 1

Bath

Sleep 7

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Exceptional(4)

$521.61

/ Nightly
Cottage

Charming Coastal Retreat with Salt Marsh Sunset Views

Fairfield, Connecticut, United States

Welcome to your perfect coastal getaway! This charming expanded Cape Cod-style home is nestled in Fairfield, Connecticut, offering a serene retreat with picturesque views of the backyard salt marsh. Designed to accommodate up to 8 guests, it’s an ideal spot for families or groups seeking both comfort and adventure.brbrKey Features:br • Spacious Bedrooms: Enjoy restful nights in four cozy bedrooms, each thoughtfully furnished to provide a peaceful sanctuary.br • Modern Bathrooms: Two full bathrooms are available, ensuring convenience and privacy for all guests.br • Inviting Eat-in Kitchen: Gather around the large kitchen table or relax by the fireplace in this warm, open space.br • Private Deck with Stunning Views: Step through the sliding doors onto a spacious deck overlooking the salt marsh—perfect for morning coffee or evening sunsets.br • Comfortable Living Spaces: The main level features hardwood floors throughout, creating a welcoming atmosphere for relaxation and socializing.brbrAdditional Amenities:br • Central Air Conditioning: Stay cool and comfortable during warmer months.br • Laundry Facilities: A washer and dryer are available on the premises for your convenience.br • Secure Entry: Wireless key entry ensures easy and secure access to the home.br • Parking: Ample on-and-off street parking is available for all guests.brbrExplore Fairfield:brbrFairfield is a vibrant coastal town offering a variety of activities and attractions:br • Beaches: Relax at Jennings Beach or Sasco Beach, both offering sun, sand, and sea. br • Outdoor Adventures: Explore the Lake Mohegan Recreation Area, perfect for hiking, picnicking, and enjoying nature. br • Cultural Experiences: Visit the Fairfield Museum and History Center to delve into the town’s rich heritage. br • Dining and Shopping: Discover a variety of restaurants and boutiques in Fairfield’s charming downtown area. br • Proximity to Major Cities: Fairfield’s location offers easy access to New York City (about an hour by train) and New Haven (25 minutes), making it a convenient base for exploring the region. Whether you’re seeking a peaceful retreat or an active adventure, this coastal home in Fairfield provides the perfect setting for your next getaway. Book your stay today and experience the best of coastal living! Welcome to Your Home Away From Home!brbrWe’re delighted to have you as our guests. To ensure a comfortable and enjoyable stay for everyone, please take a moment to review our house guidelines:brbrGeneral Guidelines:br • No Shoes Indoors: Please remove your shoes upon entering to help us maintain a clean and welcoming environment.br • Report Damages: If you notice any property damage upon arrival, kindly inform us immediately so we can address it promptly.br • Respect the Space: Please leave the premises in the same condition as you found it.br • Conserve Water: Be mindful of water usage during your stay to help us preserve this valuable resource.br • Toilet Use: Only toilet paper should be flushed; please avoid flushing other items to prevent plumbing issues.br • Clean Clothing: Refrain from sitting on furniture and beds with wet or dirty clothing to keep our home comfortable for all guests.br • Smoke-Free and Substance-Free Environment: To ensure a healthy atmosphere, our home is both smoke-free and drug-free. This includes tobacco, cannabis, e-cigarettes, and all other substances. We kindly ask all guests to refrain from using any such substances on the premises. Smoking inside the unit will result in an excessive cleaning fee of $1,000.brbrTrash and Cleaning:br • Waste Disposal: At the end of your stay, please place trash and recycling in the appropriate bins next to the garage. Use the green bin for regular trash and the blue bin for recycling.br • Adherence to Guidelines: Proper sorting is essential; failure to comply may result in a $50 fine.brbrSpecial Considerations:br • No Parties or Events: To maintain a peaceful environment, parties and events are not permitted on the property.br • Guest Age Requirements: The primary guest making the booking should be at least 25 years old. Guests under 25 are welcome when accompanied by an adult.br • Unauthorized Activities: Engaging in illegal activities or hosting unauthorized gatherings will result in immediate eviction without refund.br • Registered Guests Only: Only the specified number of guests approved at the time of booking are allowed on the premises. Any changes must be approved by the host before your arrival.br • Overstay Fees: Unauthorized late check-outs will incur a fee of $100 per hour for up to 2 hours, after which a $1,000 daily fee will apply.br • Forgotten Items: Items left behind and requiring mailing will incur a $50 handling fee plus shipping costs.br • Quiet Hours: Please observe quiet hours beginning at 10:00 PM. Excessive noise may result in eviction without refund.br • ID Verification: The host may request IDs from all guests. If this is requested, you will be required to provide them before arrival, or you will not be allowed to stay without a refund.br • Yard Maintenance: Guests are responsible for cleaning up any garbage in the yard each night to avoid excessive cleanup fees.br • Thermostat Settings: Thermostats are set between 68-72°F (20-22°C). Please plan accordingly and dress comfortably.br • Restricted Areas: The garage and attic are off-limits to guests due to safety concerns and storage of equipment.br • Pet Policy: To maintain an allergen-free environment, pets are not permitted on the property. Undisclosed pets will result in a $500 fine.br • Agreement with Rules: If you have concerns about these rules, please consider whether our home is the right fit for you. We appreciate your understanding and cooperation.brbrThank you for choosing our home for your stay. We hope you have a wonderful time and enjoy all that our area has to offer!
Bed 4

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Bath 2

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Sleep 8

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Exceptional(3)

$1979.12

/ Nightly
Agritourism

Designer Barn House • Hot Tub, Pool, Fire Pits & Entertainers Retreat

Fairfield, Connecticut, United States

A holiday-decorated barn home designed for families and groups! The big living room opens to a patio with a pro outdoor-kitchen, large pool, wood-burning jacuzzi, fire pit, and a huge open yard. Inside you’ll find a giant fireplace, huge TV, and extra-large couches everyone can pile onto. Walk to the beach, restaurants, shops & train. Just 1 hour from NYC. Add our duplex guesthouse for even more space.brbrEnter through a gated driveway to find ample parking, professional landscape lighting, and a huge yard perfect for running around with kids or hosting events.brOutdoor amenities include:brbrSeasonal heated pool + attached jacuzzibrYear-round wood-burning hot tub tucked into a cozy cornerbrFull outdoor kitchen: sink, grill, pizza oven (with manual), prep spacebrOutdoor shower (fenced & private)brDining terrace for large groupsbrAdirondack fire pit loungebrPool loungers + oversized egg chairs that each fit two comfortablybrbrThe entire property feels private, peaceful, and truly special—especially at night when the trees and grounds glow under the custom lighting.brbrThe Barn HousebrbrA striking architectural barn, full of character, comfort, and generous space for groups.brbrThe Great RoombrbrWalk in through double doors overlooking the pool and you’re greeted by a soaring barn interior with a dramatic spiral staircase and:br6-sofa conversation areabrGiant walk-in wood-burning fireplacebrExtra-large flat-screen TVbrBooks, board games, cozy blanketsbrPerfect for movie nights, game nights, or holiday gatherings.brbrDining & Entertainingbr12-person dining table (extra chairs provided)brAntique mirrors and stylish sitting areasbrLarge Alexa speakers to play your favorite musicbrbrChef’s KitchenbrA bright French country kitchen fully stocked and ready for serious cooking:br6-burner Wolf rangebrTwo ovensbrMicrowave, dishwasher, large refrigeratorbrKitchenAid mixer, blenderbrBoth Nespresso + Keurig machinesbrService for 20+ (plates, glassware, wine & cocktail glasses)brComplete grill & BBQ toolsbrIf you break a specialty glass, just let us know so we can replace it.brbrBedrooms in the Main HousebrPrimary Suite – Ground LevelbrKing bed with wireless chargersbrSunlit luxury bathroom: double sinks, large soaking tub, and steam showerbrbrWing 1 – UpstairsbrbrBedroom 1: King bed, skylight, closetbrBedroom 2: Two queen beds + sitting areabrBoth share a full bathbrbrWing 2 – Opposite Side of BarnbrbrLarge A-frame bedroom with star-gazing windowsbrPrivate workspace + sitting roombrSmaller A-frame bedroom brShared bath brbrAdditional half bath near the kitchenbrbrLaundry room available for your usebrbrFor additional space, a stunning 1-bedroom duplex guesthouse overlooking the pool and meadow is available to add to your stay for an extra fee. View it under our “Multi-Family” listing or reach out for details.brbrWhy Guests Love UsbrbrTons of indoor + outdoor spaces to spread outbrStylish, well-kept, thoughtfully designedbrGreat for children, families & multi-generational groupsbrWalkable locationbrOnly one hour from NYC, yet feels like a tranquil country escapebrCozy, elegant, festive, and perfect year-roundbrbrWe Can’t Wait to Welcome You!brbrWhether you’re relaxing by the pool, making pizzas in the outdoor kitchen, gathering around the fire, or unwinding in the hot tub, this home was designed to create cherished memories.brbrMessage us anytime with questions—we’re here to help you have an unforgettable stay!
Bed 5

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Bath 3

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Sleep 12

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Exceptional(33)

$694.55

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Cottage

Charming Fairfield Beach Cottage

Fairfield, Connecticut, United States

Escape to our newly renovated waterfront cottage in Fairfield, just steps from a private beach on the Long Island Sound. This charming retreat is perfect for families and couples, offering a modern kitchen, private deck, and high-speed WiFi. Unique perk: Enjoy complimentary 24/7 access to a beautiful co-working space just 3 miles away. A perfect blend of relaxation and productivity awaits!brbrThe SpacebrWelcome to your charming waterfront retreat, a newly renovated beach cottage designed for the perfect getaway. The open-concept living space is filled with natural light, blending rustic seaside charm with contemporary comfort.brbrKey Features & Amenities:br* Living Area: Comfortable seating, a large dining table, and a smart TV equipped with an Amazon Alexa and Fire Stick for effortless streaming.br* Kitchen: A modern, fully-equipped kitchen with stainless steel appliances, perfect for preparing home-cooked meals.br* Family-Friendly: We provide a high chair, Pack `n Play, children`s books, and toys to make traveling with little ones easier.br* Outdoor Living: Enjoy the private deck with a BBQ grill and dining set, or relax in the shady hammock.br* Recreation: Two bikes are available for a spin into town, and a kayak is provided to explore the coastline.br* Work & Connectivity: Stay connected with high-speed WiFi. Your stay includes complimentary 24/7 access to B@Work, a beautiful co-working space 3 miles away overlooking a lake and waterfall.brbrAccessbrGuests will have private and exclusive access to the entire cottage and its grounds. This includes all interior spaces, the outdoor deck, and the yard. Your stay also includes dedicated right-of-way access to the private beach located directly across the street.brbrDetails to Notebr* Beach Access Details: You have right-of-way access to the private beach across the street. Please use the designated path and avoid our neighbor’s driveway. Your beach access starts approximately 20 feet from the picket fence and extends to the high tide line.br* Respect for Neighbors: Please be respectful of our neighbors` property and follow all Town of Fairfield ordinances to ensure a peaceful experience for everyone.brThe most important House Rule is, respect our neighbors and community. Mystic is a quaint, coastal New England town. As hosts, and guests, we share in the responsibility of keeping Mystic a great place to visit, and to LIVE. Honor the noise ordinance. Be the guest that you would want staying in a vacation rental near your home.brbrWe provide detailed instructions for using our Right of Way, to access our Deeded Beach Rights across the street.
Bed 3

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Bath 2

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Sleep 7

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