Vacation Rentals By Owner In Bokeelia, FL

Escape to your own slice of paradise in Bokeelia, where tropical charm meets spacious comfort and laid-back island living.brbrThis beautifully designed retreat features two expansive master suites—one offering two king-size beds and the other two queen-size beds—making it ideal for large families, couples traveling together, or group getaways. Everyone has room to spread out and relax in style.brbrInside, you'll find two separate living areas, each equipped with a sleeper sofa featuring two full-size beds, providing flexible sleeping arrangements for additional guests. Whether you're gathering for movie night or enjoying quiet downtime, the layout offers the perfect balance of togetherness and privacy.brbrStep outside into your private backyard oasis and take a dip in the heated pool, lounge under the Florida sunshine, or unwind after a day of exploring. Two complimentary bicycles are included so you can cruise the neighborhood and soak in the island atmosphere.brbrLocated just minutes from waterfront dining, world-class fishing, local marinas, and breathtaking Gulf Coast sunsets, this home puts you right in the heart of everything that makes Bokeelia so special.brbrPet-friendly with a $150 pet fee (up to two pets), so your four-legged family members can join the adventure too.brbrBook your stay today and experience the ultimate Florida island getaway!

Bokeelia Oasis! Heated Pool, Sleeps 12!

Bokeelia, Florida, United States

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Bath

Sleeps

$174.9

Amazing privacy, very quiet backyard pool area with gas grill. Excellent fishing and close to art studios and fine dining as well as pub fare and live music.brQuick boat ride to Boca Grand, Fort Myers Beach and Sanibel. E bikes , paddle board and 2 kayaks available for guest use. 3 queen beds, perfect for a group getaway. With amenities like AC, iron, and heating, guests can relax comfortably. Excellent high speed for remote workers and beautifulbrMorning sunrise to work in peace and quiet. Come see and hear the wildlife of Bokeelia. You’ll see many bird species, tons of quiet walking trails. Also Uno our resident dolphin loves to come to the marina, just 5 minutes drive away.

Beautiful sunrise 3-bedroom pool home

Bokeelia, Florida, United States

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Bath

Sleeps

$709.29

Welcome to your private waterfront retreat in beautiful Bokeelia—where coastal luxury meets effortless island living. Perfectly situated with direct Gulf access, this stunning home is your gateway to some of Southwest Florida's most sought-after destinations, including Cayo Costa, Boca Grande, Sanibel, and Captiva.brbrDesigned with both relaxation and adventure in mind, this spacious property offers everything you need for an unforgettable stay. Bring your boat and tie up right at the dock (please note: no boat lift available), with plenty of room for your trailer and access to a neighborhood boat ramp for easy launching. Enjoy days on the water, then return home to clean your fresh catch at the on-site fish cleaning station. For those who prefer to explore at a slower pace, two kayaks are available, along with convenient dock space to launch them.brbrThe outdoor living space is truly exceptional. Take a dip in the heated pool and spa, unwind around the fire pit, or gather with friends and family in the outdoor living room. The fully equipped outdoor kitchen, complete with an outdoor bar and seating for four, makes alfresco dining and entertaining a breeze—all while soaking in serene waterfront views.brbrInside, the home showcases a beautifully updated coastal-modern design with thoughtful touches throughout. The main level features three bedrooms, including a luxurious primary suite with a king-size bed, spa-like bathroom complete with a soaking tub and rainfall shower, and a peaceful retreat to recharge. Two additional guest bedrooms each offer queen-size beds and share a well-appointed bathroom. A full laundry room adds convenience for longer stays.brbrUpstairs, start your mornings at the dedicated coffee and espresso bar before heading out for the day's adventures.brbrDownstairs, a private suite provides additional space and flexibility—ideal for extended family or guests. This level includes a king-size bed, full bathroom, comfortable living area, kitchenette, and its own laundry room. For a fun touch, you'll also find a frozen margarita machine and a full-size ice maker—perfect for cooling off after a day in the sun.brbrWhether you're boating to nearby islands, lounging poolside, or enjoying sunset cocktails by the water, this Bokeelia escape offers the perfect blend of luxury, comfort, and coastal charm.

Bokeelia Daydreamin' Incredible 4 bedroom with Pool!

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(33)

$193.9

Come enjoy a beautiful gulf access condo in Bocilla Island Club, at the northern tip of Pine Island. Enjoy your morning coffee, watching the sunrise with a view of the dolphins swimming in the canal and Jug Creek, from both the master bedroom and living room lanais. The main floor has a fully equipped kitchen, half bath, large living/dining area. The master suite has a king-sized bed with your own attached bathroom with double sinks and a walk-in shower. The second bedroom has a queen-sized bed, a twin sized cot, and a tub/shower combo. Every room has a HDTV with cable television and internet access available. There is also a washer and dryer. br If fishing is what you're looking for Some of the best fishing in SWFL can be found on the private 400-foot pier on Charlotte Harbor. You might even see some the manatees swim by the pier. Community amenities include two swimming pools, two tennis courts, two clubhouses, an on-site marina with boat launch. Lush, tropical foliage compliments this resort. There are two amazing restaurants that are minutes away from the condo. Staying on Pine Island will provide you with warm tropical weather, endless water views, an abundance of varieties of birds, dolphin playing, mullet jumping, and gorgeous sunsets ~ not to mention some of the best fishing in the world.

Condo

Paradise awaits you at the Bocilla Island Club on Pine Island Florida.

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(1)

$120.79

This is my personal dream getaway I’m newly sharing with avid travelers looking to escape their hectic lives and live in what feels like home away from home. Relax on the front porch or watch the sunset off the back porch or grab a drink and walk over to the dock where everyone gathers to chat and watch the most amazing sunsets. Kayak in the bay or rent a boat and head to the neighboring islands or catch your fresh fish for dinner.

Private Hideaway in Pine Island community Pool and Marina a few steps away.

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(11)

$261.6

Summary:brbrMermaid Haven at BocillabrbrbrbrThe Space:brbrBeautiful sunrises and sunsets over Jug Creek await you at this charming townhouse. You'll be able to enjoy them from one of two private, screened-in balconies that allow for boat watching and occasional dolphin sighting! Comfort comes easy at this townhouse, with each upstairs bedroom featuring an en suite bathroom to guarantee privacy. If someone needs to complete remote work or research fishing spots, one bedroom features a desk workspace with a creek view. The full kitchen features everything you need to cook up your catch of the day, or you can head down to the shared charcoal grill for an extra char. Feel free to toss your creek clothes into the private washer/dryer right when you get in. In addition to being just a short distance to open water, guests will also have access to a shared outdoor pool, tennis court, and shuffleboard during their stay. Central air conditioning will keep everyone cool inside, and you can close the room-darkening shades for a restful nap whenever you need one. Watch sunsets from the private association pier and throw a line in the water too!brbr brbrbrbr bTHINGS TO KNOW/bbrbr • The living room sofabed provides an extra sleeping spacebrbr • This condo does not have a boat slip, but there is a pay for use boat launch and trailer parking just down the road. brbr • World-class tarpon fishing is available in the area, as well as flats fishing for Redfish and Snook. Local fishing guides can be hired if you don’t have your own boat.brbr • There is a community dock where guests can fish and watch sunsets.brbr • Step aboard the nearby water taxi for a trip to the famous Cabbage Key and North Captiva.brbr • Rent a kayak to paddle round the bay and local islands.brbr • Visit the locally renowned Jug Creek Marina for live music.brbr • Snowbird-friendly. Contact us for details.

First-floor, snowbird-friendly townhouse w/ shared pool, WiFi, central AC, & W/D

Bokeelia, Florida, United States

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Bath

Sleeps

$446.12

Summary:brbrSalty SalutationsbrbrbrbrThe Space:brbrWelcome to your serene getaway in Bokeelia, FL! This charming single-level home offers the perfect blend of comfort and convenience for both families and adventure seekers. Featuring a spacious layout with a king bed and a queen bed, it comfortably accommodates your group. Modern amenities include central AC, high-speed internet, and a fully equipped kitchen with a fridge, stove, oven, and dishwasher—making meal prep a breeze.brbr brbrbrbr Step outside to take in the bay view, fire up the gas grill for an outdoor cookout, or lounge in the provided beach chairs. The property’s peaceful setting is just moments from the ocean, offering easy access to kayaking, fishing, and beachcombing. At the end of the street, guests can enjoy a private dock with boat access to all the barrier islands and nearby marinas such as Four Winds and Jug Creek. While exploring the area, be sure to enjoy local arts and crafts in Matlacha and browse the fresh, vibrant fruit markets on Pine Island.brbr brbrbrbr Families will appreciate thoughtful extras like a high chair, Pack-N-Play, and a collection of books and games for indoor fun. After a day of adventure, gather in the cozy living room to watch Netflix or share stories around the dining table. Additional amenities include adult bikes, beach towels, and plenty of kitchen essentials to make your stay comfortable.brbr brbrbrbr Whether your goal is to unwind or explore, this Bokeelia retreat is the perfect home base for your Florida vacation. Book your stay today and experience the very best of island living!

Charming home near the ocean with gas grill, AC & Wifi

Bokeelia, Florida, United States

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Bath

Sleeps

$416.04

Summary:brbrBowline OasisbrbrbrbrThe Space:brbrEscape to paradise at this stunning new waterfront pool home located in one of the most desirable locations in Bokeelia. Situated on a deep canal with quick access to Charlotte Harbor and a boat launch across the street, this home is a haven for fishing enthusiasts, boaters, and beach lovers alike. Step inside to discover a beautifully appointed interior featuring 18' tile flooring, a gourmet kitchen with stainless steel appliances, granite countertops, and solid wood cabinetry.brbr brbrbrbr Relax and unwind in the screened lanai with a salt-water chlorinated pool and paver deck. With hurricane impact windows, 10' ceilings, and 8' doors throughout, this home offers both luxury and peace of mind. The home also offers a boat ramp located across the street.brbr brbrbrbr Enjoy a range of amenities including a hot tub, dog-friendly accommodations, central AC, internet access, and a gas grill for outdoor cooking. The spacious deck and patio furniture provide the perfect setting for al fresco dining and lounging under the Florida sun.brbr brbrbrbr Explore the charming town of Bokeelia, with its waterfront restaurants and scenic marinas, or venture out to nearby attractions such as the Pine Island Zoo, botanical gardens, and pristine beaches. Whether you're seeking adventure or relaxation, this waterfront retreat offers the perfect blend of luxury and comfort for your next vacation. Book your stay today and experience the best of island living in Bokeelia!

Spacious, dog friendly home with pool, on waterway within minutes to the Gulf

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(48)

$492.19

Summary:brbrBocilla BreezebrbrbrbrThe Space:brbrGet a feel of old Florida when you choose this stilted, canal-front house at your home base. Ideally situated on Pine Island's north end, this home features vaulted ceilings, French doors, beautifully burnished floors, and Tommy Bahama décor throughout. Kick back for movie nights on the flatscreen TV in the open-concept living room. The pristine kitchen is equipped with stainless steel appliances, including a French-door refrigerator and a breakfast bar with seating for four. Enjoy the coastal breeze with alfresco meals on the deck, appointed with a gas grill and canal views. Read a book in the hammock.brbr brbrbrbr At Bocilla Breeze, you'll be just steps away from one of two shared pools, and the dock is only 35 feet from the house. When it's time to wrap up an evening, find two well-furnished bedrooms, adult-grade bunk beds, and a queen trundle bed in the loft. A side balcony faces the marina and is accessible from each bedroom. When it's time to head to the water, you'll have beach chairs and towels to bring along, and there are complimentary bikes and kayaks to use as well. Added amenities include a desk, free WiFi, a private washer/dryer, and access to shared tennis courts. Boca Grande Pass is just a short boat ride away.brbr brbrbrbr bTHINGS TO KNOW/b

Stunning canal-front home with pools, AC, W/D & hammock

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(1)

$460.34

This is our personal vacation home in paradise, and is only available as a rental a few times a year. Take advantage of this amazing opportunity to escape to island living! brOur beautiful Seagull Bay 3-bedroom, 2-bath waterfront pool home on Bokeelia Island, is located on Pine Island in SW Florida. With space for up to 6 adults and a child, this property blends luxurious comfort and Old Florida coastal charm with all the amenities you need for a memorable getaway. This peaceful retreat offers all the comforts of home including a fully stocked kitchen. Enjoy mornings watching dolphins and manatees in the bay from the screened lanai, take a dip in the pool, and enjoy the sunset while grilling or enjoying a cocktail at the outdoor, poolside bar. The community also has a private beach with seating for residents and guests on the gulf side.

Angler's Luxury Waterfront in Bokeelia - Infinity Pool, Bar & Dock for Fishing

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(7)

$334.5

Private Pool Retreat in Bokeelia | Pine Island’s Hidden Gembrbr-3BR/2BA beautifully remodeled home with private heated pool + screened lanaibrbr-Located in Bokeelia, Pine Island – 45 min from RSW (Fort Myers)brbr-Kayaking | World-class Fishing | Island Hopping | Stunning SunsetsbrbrbrbrWhy Guests Love This Home:brbrPrivate Heated Pool & New Screen Enclosure – swim year-round, bug-free, in your own tropical oasis.brbrSpacious Open Layout – modern kitchen + airy living space perfect for families or groups.brbrPeaceful Location – tucked away on Pine Island, a quiet Gulf Coast escape with no high-rises or traffic lights.brbrClose to Adventure – kayak mangroves, hop on a water taxi to Cabbage Key, or fish some of Florida’s best waters.brbrLocal Charm – enjoy Tarpon Lodge sunsets, Miceli’s live music, and The Blue Dog’s famous seafood.brbrbrbrThe Space:brbrYour one-level getaway features:brbr-3 Bedrooms / 2 Bathrooms – comfortably sleeps 6br-Fully Stocked Kitchen– modern appliances + dining areabr-Bright & Airy Living Room – open floor plan, stylish coastal décorbr-Private Heated Pool – with brand-new pool cage and walk-out accessbr-Outdoor Dining & Lounging – perfect for morning coffee or sunset cocktailsbrbrExplore Pine Island:brbrPine Island is a laid-back island paradise known for its small-town feel, natural beauty, and adventure:brbrFishing Charters– tarpon, snook, redfish & morebrbrKayaking & Paddleboarding – explore serene mangrove tunnelsbrbrIsland Hopping – day trips to Sanibel, Captiva, Cayo Costa & Boca GrandebrbrLocal Culture– visit art galleries, the Calusa Heritage Trail, and outdoor island marketsbrbrNature & Sunsets – quiet piers, birdwatching, and breathtaking evening skiesbrbrbrbrDining Nearby:brbrOn Pine Island: Tarpon Lodge (fine dining + sunsets), Miceli’s (Italian + live music), The Blue Dog Bar & Grill (local seafood + craft beer)brbrIn Cape Coral (15–20 min): Rumrunners (upscale waterfront), Lobster Lady (lobster specialties), Ford’s Garage (American classic), The Boathouse Tiki Bar & Grill (casual waterfront).brbrbrbrGetting Here:brbr* Fly into RSW Airport (Fort Myers, FL)brbr* Scenic 45-minute drive to Pine Island – no bridges or tolls beyond Matlacha’s colorful art villagebrbrbrPerfect For:brbr-Families looking for a pool home near beaches & activitiesbr-Couples seeking a peaceful, romantic Gulf Coast retreatbr-Snowbirds wanting a long-term Florida escapebr-Fishing & boating enthusiastsbrbrbrWe’d love to host you. Book now and start your Pine Island Getaway adventure!

Private Heated Pool Home - Pine Island Getaway - One-Level, 3-bedroom, 2-bath

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(33)

$267.31

Bring the boat, kayaks, bikes and water toys. This high and dry Pine Island home on a canal has withstood all the storms with no water damage. The house is on stilts so it remains safe from storm surge. A short trip down the canal with your boat takes you to Jug Creek, into Charlotte Harbor and out to the Gulf of Mexico in 15 minutes, where the best fishing in the world happens. brGo up the stairs to the living space where you will feel like you are in a treehouse. There are 2 bedrooms and 1 bathroom, a fully stocked kitchen with all new Fridgidaire appliances, living room, dining room, and screened in deck overlooking the canal and fruit trees.brThe main bedroom has a king size bed with storage as well as a large dresser and huge closet. The 2nd bedroom has 2 twin beds, dresser and big closet. The living room has a queen sleeper sofa. We supply all the comforts of home for short or extended stays. We have added a newer air conditioner, hardwood floors and new roof in 2022.brPlenty of seating options for the whole family. brDownstairs there is a laundry room for guest use with a washer, dryer, folding table and a freezer to store your ice, bait and the day's catch. A rolling rod rack rack is there to store your rods safely. There is a locking dock box for your use to safely store your fishing gear. We also provide a gas grill, kayak rack, and bike rack. Relax and enjoy your fresh catch and a cocktail under the carport while watching the fish jump in the canal.brThe dock has electric, fresh water, fenders and cleats to tie up your boat up to 26 ft. long. Sorry, the boat lift is not for guest use. The boat launch ramp is 3 streets away and there is ample parking for your trailer and vehicles.brbrThe 3rd bedroom, downstairs, is the Captain's Quarters. It has a queen storage bed, full bathroom and mini kitchen. It is not rented to a separate party. Maximum guests is 8 persons in the house. No exceptions.brbr***** As of Nov 21, 2025 Lavender's Landing boat ramp is open for launching. It is closed at night until the rest of the renovations are complete. For more info go to leegov.com for updates.brbrThanks for checking us out. Come see us. WE ARE AVAILABLE.

Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.

Bokeelia, Florida, United States

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Bath

Sleeps

Exceptional(2)

$308.86

Discover this whole top floor penthouse unit in a beach lodge on a small private beach in Bokeelia. Guests enjoy view of the gulf from the bedroom and the living room. Bring your own kayaks to enjoy the serene waters of the gulf and use the dock to fish. Enjoy the small private beach to relax. Bedroom has a king bed The awesome living room offers a sofa bed and a murphy bed, perfect for extra guests or relaxing evenings.. Whether you’re unwinding after a day of exploring or enjoying quiet moments inside, this penthouse provides a welcoming retreat. We think our place will help you experience everything Bokeelia has to offer.

Whole top floor penthouse unit in a beach lodge in Bokeelia on a small beach

Bokeelia, Florida, United States

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Bath

Sleeps

$256.04

Discover the beauty of Bokeelia from Snook suite a Wonderful 1-bedroom suite in a beach lodge in charming Bokeelia with expansive views of the gulf from the living room . This charming space features a 2 queen beds and a full bathroom with a full kitchen and a living room. Guests can enjoy a comfortable stay with small private beach just for the guests of the beach house lodge. Bring your own kayaks to experience the warm waters of the gulf or use the dock to fish the waters of the gulf. Whether you’re unwinding after a day of exploring or starting your morning with a fresh breeze, this adorable suite offers a welcoming retreat. Feel free to reach out to us during your stay – we’re happy to suggest local spots to check out.

Snook suite a Wonderful 1-bedroom suite in a beach lodge in charming Bokeelia

Bokeelia, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$200.94

Snapper suite is a 1-bedroom full unit in a private beach lodge is a perfect escape for you in Bokeelia Pine island , Guests will enjoy a welcoming space featuring a king bed and a cozy living room with a futon for extra comfort and can straight onto a small private beach in Pine island . The unit has a full Kitchen and a bathroom, The unit is comfortable no matter the season. Whether you’re here for a quick getaway or a longer stay, this charming spot offers a peaceful retreat. We look forward to hosting you at our place. Bring your own kayaks to enjoy kayaking straight off the property or fish off the dock.

Snapper 1 bedroom ground unit in a beach lodge in charming Bokeelia pine island

Bokeelia, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$89.66

This is a two bedroom, one bathroom, 950 sq. ft. apartment, located on the first floor of a duplex. It is situated on a quiet, dead-end road, with no traffic, and within walking distance to Pine Island center, the Pine Island Pool, Library, tennis courts and playground. This apartment has a large full kitchen, with a double oven, it is an open floor plan for the living, dining and kitchen area. Down the hall you will find the master bedroom, with a queen bed, a very roomy bathroom with a tub shower, and a 2nd, smaller bedroom with a twin bed. Both bedrooms have ample closet space, there are also two hall closets. It has a covered patio outside for you to sit and relax. This apartment has been recently remodeled with new luxury vinyl flooring, new light fixtures, ceiling fans, sink fixtures and paint, as well as a new air conditioner system.

Cozy retreat walking distance to restaurants and attractions. Pet friendly.

Bokeelia, Florida, United States

Bed

Bath

Sleeps

Exceptional(47)

$255.53

Heated Salt Water Pool and Spa on Marble Lanai, with large screened enclosure. This side-by-side home is fully equipped with appliances, linens, 2 kayaks, 2 bikes - just pack your bags for this vacation rental! Don't forget to BYOB... Boat* that is! (*contact Host for more information) Free use of ramp and slip, with shallow canal access to Matlacha Pass and Charlotte Harbor/Cayo Costa/North Captiva islands. Bokeelia is truly a forgotten paradise... once you drive over the bridge through Matlacha, you'll feel the vibe... fishing village, festive shops, variety of dining options, parks, sunsets, canals... you'll be surrounded by happy wildlife... dolphins, manatees, eagles, osprey, egrets, ibis, herons... even 2+ resident Gopher Tortoises on our property (look but DON'T touch or feed!) Even the Palm Trees love it here (Pine Island is the palm tree growing capital of the region!) Be aware there are no public beaches on Pine Island, which is surrounded by Gulf waters and bordered with mangroves. Ferries available to the barrier islands, one hour drive to Ft Myers beach. brHosts (retired, 60-ish couple) occupy the other unit of this duplex and are very respectful of their guests' privacy. brThe large pool/spa/lanai area is shared, with each unit having its own full set of loungers, chairs, firepit, and private outdoor dining area.

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

Bokeelia, Florida, United States

Bed

Bath

Sleeps

Exceptional(10)

$322.41

Welcome to Sonny Palms. This Direct Gulf Access Home has been completely remodeled in fall of 2021. This home offers: 3 bedrooms, 2 bathrooms, custom kitchen, den, spacious family room and a screen patio area that you will never want to leave. Home features a dock so bring your boat. Outside shower is perfect when coming off the water after a long day of boating, swimming and fishing. Bring your RV too, because this home has an RV Pad with 50 AMP service. Home is GORGEOUS inside and boasts an extra large outdoor paved area. Located in Charlotte Shores Community - Bokeelia, on Pine Island with access to Open water and 45 minutes to Cayo Costa, Cabbage Key- Boaters Paradise! Pool added winter of 2024. New Dock with fishing brstation 2025. ***** PLEASE NOTE DOGS ARE EXTRA AND MUST BE APPROVED BY THE OWNER .......... WE ARE VERY DOG FRIENDLY BUT YOU MUST LET US KNOW!!!!

Welcome to our piece of Paradise! Great location for everything Pine Island

Bokeelia, Florida, United States

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Bath

Sleeps

$177.24