58,368 properties available

Located in Bokeelia, Florida, United States. Bokeelia Cottage w/ Private Pool & Tiki Bar! Find a tropical paradise in your own backyard at this 2-bedroom, 2-bathroom Bokeelia vacation rental cottage! With all of the amenities of home, this mini-oasis provides guests with luxury in the form of a private swimming pool, lanai patio, and a convenient location close to beach activities such as snorkeling and kayaking along Matlacha Pass and Pine Island Sound! Set on the beautiful Pine Island, this home allows you to enjoy Old Florida charm during your rejuvenating stay.-- THE PROPERTY --< 3 Mi to Beach | Washer & Dryer | Pet Friendly w/ FeeBedroom 1: King Bed | Bedroom 2: Queen Bed | Living Room: Sleeper SofaKITCHEN: Refrigerator, stove/oven, microwave, dishwasher, drip coffee maker, dishware & flatware, spices, cooking basicsINDOOR LIVING: Smart TV, dining table, ceiling fans, board games, booksOUTDOOR LIVING: Private pool, screened-in lanai, gas grillGENERAL: Free WiFi, laundry detergent, towels, linens, central air conditioning/hea

Located in Matlacha, Florida, United States. Comfortable and relaxing house located on a deep water canal. Cute little house located on a deep water canal in the heart of Matlacha. The primary bedroom has a king-sized bed and the second bedroom has a trundle bed opening into two single beds. The couch in the living room opens to a queen-sized bed. There is Xfinity cable in the living room and wifi. There is a complete kitchen and a washer and a dryer located in the garage. The back lanai has an electric grill, a large table, comfortable seating for 6, and 2 lounges. There is a dock where you can tie up your boat. Pets are allowed and you are expected to pick up after your dog.

Located in Bokeelia, Florida, United States. Soak up Paradise as you Relax in Pool/Spa Home surrounded by Happy Wildlife New in 2021 Heated Salt Water Pool and Spa on Marble Lanai, with screened enclosure. This side-by-side home is 7 years young, and 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! 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, 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 Isla

Located in Matlacha, Florida, United States. Studio#1-Back Bay Sunsets in Matlacha Take it easy at this unique and tranquil open water getaway - perfect for the solo traveler or a couple. Oversized closet space for longer stays. Brand new custom tiled shower and separate bathtub in this beautiful master suite with private entrance. Efficiency kitchenette provided with a microwave, refrigerator, coffee maker, and toaster. Stay a day or stay a month! You are welcome here! Private entrance attached to the mini villa.Brand new king bed studio for 2! Separate shower and bathtub, spacious closet, and kitchenette in comfy quarters with million dollars sunset views!You are staying at the Matlacha cottages. There are 3 other units who share the beautiful backyard space which share the beautiful wildlife and sunset views.Pine Island Community Pool is $3 for adults! It’s close and amazing!

Located in Bokeelia, Florida, United States. Sophisticated home with private pool & fast WiFi - walk & ferry to attractions Eagles NestOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Decorated with beachy touches throughout, this home is ready to be your fun vacation retreat! The private saltwater pool with lanai is perfect for a dip or two. Or, grab your favorite book and relax on the lounge chairs or hammock for added leisure. Enjoy cooking in the full kitchen, equipped with luxuries like a French door refrigerator and kitchen island, then store your wine and snacks in the outdoor kitchen for easy-to-grab refreshments. Cooking on the private gas grill is always an option, of course. Central air-conditioning and a ceiling fan in every bedroom will keep every guest comfortable. There's also a TV in every bedroom so everyone can wind down with their favorite shows. If someone has remote work or homework to finish, there's a workspace in the mai

Located in Bokeelia, Florida, United States. Prettiest Sunset View Pine Island, Waterfront Home on Water Welcome This is the fishermans delight. In addition to staying in the house with the prettiest sunset views on Pine Island, you are right across the street from the best spot on Pine Island to launch either kayaks or simply wade out for fishing. You are also walking distance from the Pineland marina. The home is also on the old Calusa Indian's canal right behind the Calusa Indian mounds, there is a state park established in the last 5 years that has a fun walking trail, there are several plackards that explain the history of the people that lived here 500 years ago. The nature walk wanders for about a half mile 50 yards behind the home. When you walk around the grounds you will feel that you went back in time. Again you are also in the house that sits front row to prettiest sunsets on Pine Island. The double kayak and old windsurfing rig come with the rental of the house, jus

Located in Matlacha, Florida, United States. Key West Style Home w/ Hot Tub and Boat Lift in the Heart of Matlacha! Two-story Key West style stilted home in the heart of Matlacha! You will have the home to yourself! The first floor is is perfect for entertaining with screened in porch and hot tub. Second floor is private and tranquil with screened in balcony overlooking the water and treetops! Home is a 2 bedroom, 2 bathroom, with additional bonus space with trundle bed. Home is perfect for fishing or kayaking with boat lift and cleaning station. There is a double driveway that is perfect for boaters bringing a trailer. Visit all there is offer - walking distance to Blue Dog, Perfect Cup, and take a boat ride to Cabbage Key, Cayo Costa, or Boca Grande!

Located in Bokeelia, Florida, United States. Luxurious and Comfortable Waterfront Home with Gulf Access. Beautifully appointed two bedrooms with 2 baths. Wonderful screened pool. Full kitchen, laundry room, separate dining room. Hang by the pool, go to a local restaurant, go fishing or boating. This home has it all.

Located in Bokeelia, Florida, United States. Florida Island Paradise Home, Bokeelia Canal, Pine Island, w/Pool & Boat Lift Welcome to Island Time Inn! This 3 BR, 3 bath private home is located in Bokeelia Isles, Pine Island, Florida. Welcome to your vacation paradise, complete with a boat lift that can accommodate up to a 26' boat and is supported by a wide and deep canal. This home features an upper level with 2 large bedrooms with queen sized beds, 2 full baths, plenty of luxurious living area and a fully equipped kitchen. TVs in every bedroom, 55" screen in the living room and kitchenette. Full sized washer/dryer too. The lower level suite with private entrance has a queen bed, TV and bathroom and opens to the lower level kitchenette complete with a full sized refrigerator, microwave, coffee maker, blender, TV, sink, and counter. Beautiful mature palm trees and tropical landscaping offer privacy. Relax and unwind while listening to the gentle sounds of the waterfall in the beautifully landscaped pool. Pine Island i

Located in Bokeelia, Florida, United States. Has all of the modern comforts-hidden in the palm and mango groves. Perfect for those seeking a peaceful retreat or just to get away for some time alone. This original Florida cracker-style house consists of the main great room, kitchen and dining areas, one bathroom and one bedroom with a queen bed. We do have a pull-out bed in the living room. It is a really cool and relaxing house. It is wired with WIFI, Local and streaming TV. There is a music collection that you have full use of. CD's, Cassettes, LP Records and Radio. The home has central air, RO Water Filtration for drinking water and ice. Your dog is welcome. Two minutes to local ramp for fishermen. Bring your boat or kayaks. Close to marinas, boat ramps and restaurants. Take the local ferry to the out-island like Cayo-Costa, Captiva and Cabbage Key for lunch. This is a secluded location, so don't be surprised if you get a visit from our local peacocks. Old Tropical Florida at it's finest. NOTE: The months of January, February

Located in Bokeelia, Florida, United States. Paradise at Serenity Cove Nestled away in a quiet community on Pine Island’s NE side, this home is an angler’s or kayaker’s paradise! The home is centrally located on the island, so you will be close to everything Pine Island has to offer - from Bokeelia, to St James City, to Matlache. Located on a private waterway, you will have endless kayaking and fishing spots at your disposal. If boating isn’t your thing, you can catch fish right off the dock, where huge snook have been known to hang out.

Located in Matlacha, Florida, United States. Reopened in November 2023 Studio "Redfish Room" in a house with 4 apartments, open water - cozy atmosphere in an open living-sleeping area with fully equipped kitchen - private bathroom with shower - the highlight: the "closed veranda" overlooking the waterEnjoy a dream holiday in a place on this earth, which offers you every evening the most beautiful sunset in the world!Our "Fishermen's Paradise" is located directly on the water. In just a few minutes you can reach the Gulf of Mexico. The view from the boat dock is towards the west - the evenings you will not want to spend anywhere else!The building complex is typical of this region - it captivates with the customary colorful colors of the south. The complex consists of 4 small, cute studios that provide everything you need for a holiday - a place to sleep and relax, a well-equipped kitchen and a private bathroom with shower. A communal laundry room offers the possibility to wash and dry laundry if necessary.However, more important a

Located in Matlacha, Florida, United States. A little piece of paradise Indulge yourself in beautiful sunsets and the peaceful island life in this one bedroom, one bathroom mobile home just minutes away from Pine Island, Cape Coral, and Fort Myers Watch the sunset and sunrise right out of your window while you sit back and unwind.

Located in Matlacha, Florida, United States. Turtle House in matlacha on the water with spectacular sunsets This peacefull yet centrally located property has all the comforts you will need for the perfect getaway or extended stay. Experience breathtaking sunsets while sitting out relaxing by the water. Walk to all shops, galleries and restaurants that Matlacha has to offer. This professionally decorated home has been completely remodeled since Hurricane and has ample space and everything you need.

Located in Bokeelia, Florida, United States. 2/2 Home in Bokeelia, Boat Lift Included! This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pine Island! This property has beautiful tropical decor to get you settled into the island lifestyle. You can relax and enjoy the views and wildlife on the back patio or grill the day's catch. This canal has incredilble Gulf access and you will be out to the intra-coastal in minutes for some of the best fishing in not just the country, but the world. Bring your boat! Boat lift included with trailer parking available in the lot next door.

Located in Bokeelia, Florida, United States. Breakaway in Bokeelia! Forget your worries in this spacious, serene home. Enjoy family, friend or alone time in this well thought out floor plan. Enter the front door into the open living/TV/kitchen/dining space. Well equipped newly remodeled galley kitchen with plenty of room for both the chef and the sous chef to comfortably prepare meals! The kitchen is open to the main living space along with a bonus room just off the dining/kitchen area that can also be closed off. Three spacious bedrooms; master has an ensuite bath and a separate sitting area. Pull out bed in the bonus room that leads to the outside patio area. New washer/dryer in the designated laundry room. The 1/3 of an acre allows for plenty of room to take in the laid back island vibe. Jug Creek marina and Lavender's Landing public boat ramp just minutes away.

Located in Bokeelia, Florida, United States. The Barrancas Barnacle! A Private Canal-Front Island Oasis w/ Dock, Sleeps 10 A one-of-a-kind Private Water-Front Bokeelia Property! Enjoy over an acre of gulf-access island living with this rare retreat. Completely updated, Ground-Level 3/3.5 Home w/ Den and plenty of room for parking, boat trailers, and more. Whether your looking for world-class fishing, shelling, beautiful beaches, amazing sunsets or just a cruise on the water, our home is perfectly positioned for easy boat-access to Charlotte Harbor, Pine Island Sound, World-Famous Boca Grande Pass, and the white sand beaches of Cayo Costa, Upper Captiva, Captiva & Sanibel. Mix up your favorite cocktail & enjoy our amazing private screened pool & patio, gaze at Sunset Skylines, stare at the stars at night, fish on the Bokeelia Fishing Pier just a bike-ride away, visit an Art Gallery, and eat at some amazing eateries on the Island! The home is perfectly set up for two couples or families to have their own private space. Guest

Located in Matlacha, Florida, United States. Yellow Fin Cabin of Matlacha Famous Matlacha island with tourism and fishing. Many restaurants and bars at walking distance. The best fishing off a bridge and off the properties back yard. Beautiful home with 3 Bedrooms and 2 Bath.

Located in Matlacha, Florida, United States. Reopened in November 2023 !!! You will enjoy great days right here in one of the best places on earth!We guarantee the most beautiful sunset of Florida in shiny colors and with the best view, you will ever have.Our "Fishermen´s Paradise" is located just a few minutes away from the Gulf of Mexico. The house has direct access to the water with its own landing stage. The spectacular view to the west won´t let you spend your evenings somewhere else. The building complex is characteristic of Matlacha - a colorful and creatively decorated accommodation with a fresh touch and lovingly attached details.The "Fisherman´s Paradise" consists of 5 small and adorable studios. Each studio offers a queen-size bed, an eat-in kitchen, and an own shower bath. In the kitchen, you will find a mini oven with fryer and 2 induction hotplates.A community washing machine and dryer are also available as well as many different seating groups in the spacious outside area.Look forward to spending nice evenings on t

Located in Matlacha, Florida, United States. 4 Person 1 Bedroom Condo with Waterview Patio - Snapper - Welcome to our newly renovated one-bedroom condo! Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four guests, it's the perfect retreat for families or groups. Take a dip in the pool, grill out with a view, or dock your boat for easy water access. Our modern amenities and stunning location offer the ultimate in luxury and relaxation. Book now and experience the best of Matlacha in our newly updated condo!

Located in Matlacha, Florida, United States. Townhome with stunning view of Matlacha Pass Stunning Views….A unique town home community nestled on the island of Matlacha. This Matlacha location is literally minutes from the Gulf of Mexico. Within the waterfront setting of Porpoise Point our town-home has approximately 2,000 square feet of air-conditioned living space, three bedrooms, three and a half baths and three balconies overlooking the spectacular views of Matlacha Pass. The community’s Key West style buildings will evoke an Old Florida feeling with tin roofs and Hardie Board Siding, paired with the latest in building technology.Porpoise Point is surrounded by mangroves and aquatic preserves and, by boat is only minutes from world famous fishing spots areas such as Boca Grande Pass, regarded by fly fishermen and rod anglers alike as the world’s number one tarpon fishery.Our home offers truly spectacular views of Matlacha Pass and the views teem with natural wildlife – watch the ospreys fly by, pelicans dive and dolphins and

Located in Matlacha, Florida, United States. Florida Style Villa by the Water with heated Pool, Dock, Gulf access! You love the water... then this is your place to be!The villa has been completly renovated in 2024!Start kayaking or by boat exploring the beautiful beaches and Mangroves right from the dock, direct access (Lift is not available right now but small boats can be tied at the dock). Catch your fish and enjoy it for dinner....watch Dolphins pass by.... The private pool (heated) gives a nice refreshment after a day out and about.The spacePrivate heated pool, no sharing! Nestled between Cape Coral and Pine Island, Matlacha is a small, old Florida island known as the fishing capital of SWFL. It offers a one-of-a-kind coastal experience, where the local community's creativity and love for the sea shine through. Don't miss the opportunity to make this waterfront retreat your own and immerse yourself in the laid-back charm of Matlacha.Cape Coral and Fort Myers are just a few minutes away! Great white sandy beaches of nearby Sa

Located in Matlacha, Florida, United States. House on Matlacha Pass with pool, hot tub, kayak dock & 10k lb boat lift! Enjoy our spacious open concept home with a great outdoor living space that opens up fully to a lanai overlooking the Matlacha Aquatic Preserve. Wildlife abounds including a vast array of birds, fish and even the occasional dolphin! If you love to boat or fish, this is your place. The house is equipped with a 10,000 lb lift with Gem remote, floating kayak dock, ample dock space for fishing right off the dock and even a fish cleaning station. If that's not enough, hop in the heated salt water pool for a refreshing swim or for the cooler nights and mornings take a relaxing dip in the hot tub. This home is truly an Island Oasis and only a 10 minute walk to downtown Matlacha where you can take in the view at a number of great dockside dining establishments (including the famous Bert's Bar and Grill), visit the Matlacha Bridge (known as the World's Fishingest Bridge) or take a stroll and visit the many great down

Located in Matlacha, Florida, United States. 6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel Welcome to our newly renovated one-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the ability to sleep six guests, it's the perfect retreat for families or groups. Take a dip in the pool, grill out with a view, or dock your boat for easy water access. Our modern amenities and stunning location offer the ultimate in luxury and relaxation. Book now and experience the best of Matlacha in our newly updated condo!