58,368 properties available

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 the t

Located in Bokeelia, Florida, United States. Southwest Florida Home Pool Fishing Biking Hiking Sun & Fun Discover the beauty and charm of Pine Island, Florida, with our spacious three-bedroom vacation rental, complete with a large screen lanai and heated pool, golf cart, and bikes. This is the ultimate escape for those seeking a peaceful and serene getaway surrounded by all the outdoor activities and quaintness that Pine Island has to offer. Take a kayak out on the calm waters surrounding the island, guided sportfishing or fishing off the docks, or explore the lush mangrove forests on a nature hike. Whether you're seeking adventure or simply want to relax, there's something for everyone here.This rental is located just minutes from the historic Tarpon Lodge and Safe Harbor Marina, home to some of the best Gulf Coast fishing. Cast a line and try your hand at snook, spotted sea trout, redfish, and tarpon, or simply enjoy the breathtaking views of the water. The nearby marina also offers boat rental options, allowing you to explore

Located in Bokeelia, Florida, United States. Bokellia Tarpon Retreat Island life Begins here. Waterfront canal. Take Your boat to Cabbage Key Boca grande Caya costa. Tarpon Capital of the World within 15 minutes! Room for boat trailer. Two blocks from ramp. Bring boat! Has 10,000Lb Boat Lift!!!!

Located in Matlacha, Florida, United States. 2 Person Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo! Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, it's the perfect retreat for couples or business. 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. 4 Person 1 Bedroom Condo with Waterview Balcony Fisherman Cabin - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony! 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 Bokeelia, Florida, United States. Island Getaway - Monthly Rental - 3 Queen Beds Enjoy island life in this spacious and serene space. Gulf access and restaurants are in walking distance as well as boat excursions to beaches. Home’s backyard boasts a scenic palm tree farm you can enjoy while sitting by the gas fire pit. Also, 4 bicycles along with 2 kayaks are on premises. Home renovated to include new flooring along with a new kitchen with granite countertops and new appliances. Public golf courses and pool and tennis nearbyThe spaceThis home is in a 55 and over community. At least one person has to be 55 or older to rentOther things to notePlease note our home has a separate private area with its own entrance off the back of the house. This will not be utilized during your stay.The outside of the home has a security feature (ring doorbell)

Located in Bokeelia, Florida, United States. Studio Condo, just minutes from Charlotte Harbor and great island shopping! Captains Cove waterfront end unit-Studio condo, 1 Bath, second floor, with parking under unit. Queen size Murphy bed and Queen sleeper sofa. Screened patio. Kitchen has everything you need to prepare meals-4 burner stove with oven, microwave, toaster and coffee pot (12 cup). Bathroom has tiled stall shower. Fully equipped kitchen and bath with all linens. Central heat/air. Washer/Dryer under unit. Unit is 401 sq. feet.Includes the use of the community swimming pool (heated), boat docks, tennis court, and ice machine. Bring your boat and launch at the Captain's Cove HOA Boat ramp, community slips available and parking for trailer underneath unit. Just minutes to Charlotte Harbor via Jug Creek. Easy access to Sanibel, Captiva, Cayo Costa and Boca Grande by boat or Ferry. Four Winds Marina next door where you can rent a boat to explore in or fish from, buy bait, gas, and supplies. Quiet neighborhood, great

Located in Bokeelia, Florida, United States. Blue Crab Key Condo! Two Bedroom Two Bathroom! This beautiful 2 bedroom, 2.5 bath condo has everything you need to enjoy the island to the fullest!Blue Crab Key is a beautiful resort style condo complex located in serene Bokeelia. It is in one of Pine Island's finest condo communities with two heated swimming pools and Jacuzzis, two tennis courts and a nice Clubhouse. It also features free boat dockage that is available on a first come first serve basis in this community, which offers direct access to Matlacha! There is plenty of space below the condo for you to store your trailer while you are out enjoying our beautiful water ways. There is a boat ramp on site to make your boating experience even easier. Pine Island and its surrounding waterways are known for the world class fishing that you will be hard pressed to find anywhere else. If you need a place to escape the hustle and bustle of everyday life, this is it. Once you cross the bridge you enter "Island Time" and after you get a

Located in Matlacha, Florida, United States. 3/3 Home in Matlacha with Downstairs Suite! Incredible Views! Check out this 3/2 in the heart of Matlacha! Two bedrooms upstairs with deck overlooking open water and 1 bedroom suite downstairs that includes a kitchenette. Fish right off the deck and catch the freshest fish you will find in SWFL. This property sits on the main road that leads to popular shops and restaurants of Matlacha, including Miceli's, Blue Dog, The Perfect Cup and the Fudge Factory. Bring your boat! Plenty of space to tie up your boat, minutes to Matlacha pass and so much space to park your boat trailer.

Located in Matlacha, Florida, United States. Matlacha Fishing cottage This newly renovated 1940's Fishing Cottage is certain to catch your eye. Matlacha is a quiet village just on the way to beautiful Pine Island. With ample off street parking for your vehicle and your boat trailer you are to sure to find a comfortable space here on Pine Street. The community boat launch is across the street at Matlacha Park. It is a short cruise at idle speed under the Matlacha draw bridge to the 4000 lb boat lift situated in the deep water canal right at the cottage. Pine Island Sound is known its perfect areas for kayaks and canoes alike. Launching from the seawall with just a turn around the corner makes this area the perfect place for fishing and nature lovers alike. Heading due north you will also find Charlotte Harbor a nearby boat trip. Matlacha offers the Perfect Cup restaurant for a early morning breakfast before starting your day. The Blue Dog is known for their tasty seafood meals and authentic Matlacha flair. Of course, no

Located in Bokeelia, Florida, United States. Island Escape 2 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.

Located in Bokeelia, Florida, United States. Bokeelia Charming Island House Welcome to your getaway home- a newly remodeled spacious 3 beds 2 bath house, the left side unit of a duplex. Quiet and relaxing 2.7 acre property, enjoy sunset evenings on the front porch watching the palm trees swaying on the front yard. Visit Alden Pines Country Club down the road for a day on the golf course or catch the ferry from Pineland marina for a beach daytrip to famous nearby islands of Cayo Costa, Captiva and Useppa Islands. Perfect town for outdoor activities like biking, boating, fishing, sightseeing; or drive over to Matlacha for waterfront dining and shopping. Come visit one of the most natural reserved island of southwest Florida.

Located in Bokeelia, Florida, United States. Beautiful "Old Florida" Pine Island Golf Course & Marina Home This is a lovely, updated 4/3 stilt home located directly on the Alden Pines Golf Course and only 1/2 block from the Pineland Marina. The main living area (second level) is a beautifully remodeled 3 bedroom, 2 bathroom home featuring a large living room with Brazilian solid hardwood flooring, vaulted ceilings and a cut coral wood burning fireplace. A large fully stocked and appointed kitchen with breakfast bar and dining area, featuring a full size SS refrigerator, range, dishwasher and microwave. The home has three large bedrooms including a king master bedroom with a loft and large private bathroom, queen size guest bedroom and a third bedroom with two twin beds. There is a separate laundry room with washer and dryer. The kitchen and living room open up to a large screened and covered porch that looks directly down the 18th fairway of the only golf course on Pine Island. You can view the abundance of nature from your d

Located in Matlacha, Florida, United States. 8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo! Welcome to our newly renovated two-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the ability to sleep eight 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 Cape Coral, Florida, United States. Serenity Bay Studio 4 On the same property as Serenity Bay Cottages, Big House, is a 4 plex, with four studio apartments. Each about 250 sq. ft. Two face the water and two face the street. Studio #4 is water facing, it has a queen sized bed, kitchen with large convection oven, two burner cook-top, microwave, toaster and 9 cu. ft. fridge. Relax on your deck, which is steps away from the sea wall and fire pit, wait for the dolphins to come out and play while enjoying the gorgeous sunset. Room is stocked with dishes, glassware, utensils, pots and pans, as well as linens and towels. Included are the use of kayaks, as well as laundry facilities, WiFi, smart tv's offer commercial free Hulu Plus, an antennae provides for CBS, NBC, ABC, ect. No cable is offered in the 4-plex.

Located in Bokeelia, Florida, United States. Florida Pine Island Paradise Get-Away in Bokeelia Welcome to your dream vacation destination! Escape to this cozy rental property nestled in sunny Florida. Whether you're seeking relaxation, adventure, or a bit of both, this property offers the perfect blend of comfort and convenience. This recently updated 2/1 duplex home in a peaceful, quiet neighborhood has all you need for a perfect vacation: Spacious furnished interior with tasteful decor.Fully equipped kitchen with modern appliances, cookware, and utensils.Two bedrooms, each with Queen beds with cozy linens and ample storage.Full sized washer/dryer High-speed Wi-Fi throughout the property.Smart TV with streaming services for your entertainment.Private outdoor patio area for soaking up the Florida sun.Backyard barbecue grill for delightful cookouts. Fenced in yard- yes, you can bring your pet on vacation with you! Bringing a boat? For an additional fee there is a private boat lift available for your use complete with electric

Located in Bokeelia, Florida, United States. No Rat Race here at the Royal Flush. Hidden oasis, Secluded 1 bedroom apartment set amongst the Royal Palms and Mango Trees. Private entrance. Plenty of room for your boat trailer with a boat ramp nearby for access to some of the best fishing in SW Florida.Bike path, Kayaking, Fishing pier close by. Public heated pool and tennis courts on the island. Pine Island is known for its tropical fruit farms and Palm Tree farms as well as the great fishing.Our Royal Flush gets it name because of the magnificent Royal palms on the property as well as our Mango Grove. Guests are welcome to enjoy the mangos while they are here.Fully equipped kitchen as well as a gas bbq so you can cook here or dine out in one of our local restaurants. We are close to the barrier islands and Ferry's who do day trips to Cayo Costa State Park and Cabbage Key, with beautiful beaches. We are happy to recommend Captains if you wish to go fishing.No red lights on the island, but we do have supermarkets, drug store, ban

Located in Bokeelia, Florida, United States. Summer Special! Gorgeous Four Winds Condo! Come enjoy this beautiful newly remodeled 2 bedroom 2 bath condo with an amazing marina view! Four Winds Marina has The Lazy Flamingo Restaurant is on site for your enjoyment, sample some of their great dishes or have them cook up your catch of the day! There is a pool on site for your use as well. Take a dip after your day of boating or sightseeing. Four Winds full service marina offers the convenience of boat rentals, fishing charters, guided sightseeing tours and the fully stocked Ships Store. All boat dockage needs must be made with the marina directly. 30 Day Minimum*

Located in Matlacha, Florida, United States. Waterfront cottage in Matlacha, FL -Unavailable at this time due to Hurr Ian.🌴 Our paradise cottage is in the cutest, artsiest, fishingest town, Matlacha FL, on Pine Island. Clean, updated and beautifully decorated 2 bedroom/2 bathroom, with laundry room. It’s truly turnkey accommodations! Sleeps 4; twin beds can be converted to a modified king bed upon request. Full-size kitchen, oversized comfy furniture, large lanai overlooking the canal and outdoor patio with a smoke chimney for those great evening nights around the fire. Dock furniture. Cable, internet access and wireless wi-fi. Includes dock, 10k covered boat lift and direct gulf access. Just 5 quick minutes to awesome red fish/snook/trout/ and more fishing. Walking distance to downtown Matlacha for great restaurants, shopping and the small fishing village experience. Kayak around on the water to see all kinds of wildlife like birds, fish, dolphins, and an occasional manatee. If you love to boat, fish, explore, take day trips

Located in Matlacha, Florida, United States. Cottage with private deck in the heart of Matlacha This is a small cottage with an attached in-law unit, that has the option to rent the house as a 2-bed bath due to this attached in-law unit, which has its own bathroom and entrance. The master bedroom has a king-sized bed in the, there is a full kitchen with a dishwasher included. The living and dining area are an open floor plan, the wall facing the water is a large sliding door that opens out to a private deck. There is a sofa bed in the living room that opens out to a full bed.. The main bathroom has a newly tiled stall shower. The attached in-law unit has a twin daybed and a bathroom with a stall shower, a recliner, and a murphy desk. Prices are based on renting the main part of the house as a one-bedroom, one bathroom. Inquire for pricing and availability if you are interested in renting it as a two bed, two bath. There is also an added refundable security deposit for the attached in-law unit.

Located in Bokeelia, Florida, United States. Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal If you are looking to get away from it all and surround yourself in Florida's tropical nature then Pine Island is the place for you. Come enjoy Twin Palms on the water in Bokeelia, it's a fishing paradise!Our home is a lovely 2 bedroom 2 bath Key West style home. It's a place where you can enjoy yourself on the screened in porch while taking in the sights & sounds of nature that only a tropical Island can offer. There are several community boat ramps just minutes away and we have plenty of driveway parking area for storing a trailer. Enjoy the warm tropical island style interior, relax in a spacious living room with tall ceilings and abundant natural light. Lounge or dine on the screened porch overlooking a back yard area with fruit trees and waterway views. Enjoy Cable TV, wify internet, 2 bicycles, two Kayaks, a gas grill, ample parking and lower level covered patio. You are only minutes from the Philips co

Located in Tarpon Springs, Florida, United States. Snow Birds Welcome! Cozy Home close to Beaches and Sponge Docks. Adorable home on a quiet cul-de-sac less than a mile from the glistening sands of Sunset Beach. The kitchen is fully equipped for those who like to cook and the patio overlooks lush tropical landscaping for those romantic evenings outdoors. The living room has a large flat screen TV for your viewing pleasure and the house is WiFi ready so you can catch the latest on Netflix. Our Florida paradise will not disappoint as there are plenty of activities for everyone in this scenic locale.

Located in Tarpon Springs, Florida, United States. Beaches Sunset/Free Bicycles This is a SELF CHECK-IN cozy in- law apartment, it has its own private entrance, living room & bath room. Minutes to the beaches. * One block over to Sunset Beach. * 1 mile to Howard Park & Beach.* 2 miles to Historic Sponge Docks. * A 6 min to Gorgeous Innisbrook Golf Courses. The Copperhead Golf Course is the most recognizable of Innisbrook’s four golf courses and is the host course every March for the PGA TOUR’s Valspar Championship.* A 15 min to Honeymoon Island and the ferry to Caladesi Island voted consistently as one of the top 10 beaches in the US.* A 30 min to Clearwater Beach. Clearwater Beach dazzles with impeccable beaches and inviting waters. Trip Advisor named it the nation's #1 beach in 2018.There are lots of fun things in our area, there is a concert at Sunset Beach the first Thursday of each month. Sunset Beach Park is a local favorite with kite boarders, boaters, fishermen, and a perfect place to watch the Sunset. Howard Park with a beach,

Located in Tarpon Springs, Florida, United States. Waterfront Apartment Beautiful waterfront 1 bdrm/1 bath apartment, upstairs, over detached garage. Minutes from historic and colorful downtown, sponge docks, and beaches of Tarpon Springs, Fla. A hidden treasure, Tarpon Springs offers wonderful shopping and dining opportunities, fishing and boating activities, arts and craft shows and musical events without the congestion of other locales nearby. The bayous and waterways of Tarpon Sorings have earned it the nickname, “Venice of the South”. Fishing, kayaking, wind surfing, paddle boarding, and leisure boating abound. This property includes large back yard and private dock. It provides fully furnished kitchen, bath and bedroom, laundry, WIFI, cable tv, and AC. Small dog allowed. No cats (owner allergic).