Home Vacation Rentals By Owner In Bokeelia, FL

Showing 80 Of 137 Vacation Rentals
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Exceptional(4)

$248.4

/ Nightly
Private Vacation Home

Bokeelia Oasis! Heated Pool, Sleeps 12!

Bokeelia, Florida, United States

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!
Bed 2

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Bath 2

Bath

Sleep 10

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$709.29

/ Nightly
Private Vacation Home

Bokeelia Daydreamin' Incredible 4 bedroom with Pool!

Bokeelia, Florida, United States

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.
Bed 4

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Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(11)

$261.6

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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.
Bed 2

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Bath 2

Bath

Sleep 6

Sleeps

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$446.12

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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!
Bed 2

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Bath 2

Bath

Sleep 6

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$416.04

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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!
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(7)

$334.5

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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!
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(33)

$267.31

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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.
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(47)

$255.53

/ Nightly
Private Vacation Home

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

Bokeelia, Florida, United States

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.
Bed 3

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Bath 2

Bath

Sleep 5

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