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Bokeelia Vacation Rentals

We Have 76 Vacation Rental Offers Available In Bokeelia. Average Price Per Night Is $196.57. Find Your Vacation Home Today.

Showing 20 Of 76 Vacation Rentals
  • Property-1 Image 1
    Beautiful waterfront Key West style home with a pool
    Private Vacation Home $306 / Nightly
    • (4) Exceptional
    • 3 Bed
    • 4 Baths
    Bokeelia, Florida, United States

    Private, spacious Key West style home located on a canal with quick access to the pine Island sound. 3 bedroom 3 full bath living space with an open kitchen that flows into the living room. The kitchen has everything a home chef could ever need for creating any meal or entertaining family and friends brbrBeautiful hardwood floors throughout and live edge wood island bar top add a coziness to this island gem. Windows throughout the house that allow plenty of Florida sunshine in to brighten any room or day for that matter. brbrBeautiful rod iron railing follows the staircase to the upstairs loft which is complete with a queen bed and a full bath. It also offers wonderful views of the waterway behind the house.brbrWalk out of the back door and there's a screened- in balcony to lounge in...exit that and there is a spiral staircase that takes you down to the patio area complete with an outdoor sectional for entertaining or just spending time with family and friends including the four legged ones. Yes we are dog friendly here. Only ask that the dog(s) are house broken and friendly.brbrNext to that is the heated pool... The perfect place to hang out and catch some sun. brbrBeyond that is the yard that leads you to the dock. It's on a canal that is a quick boat ride out to the big water of the pine Island sound. There are pilings next to the dock so keeping a boat behind the house is not a problem, the canal is very calm. You are minutes away from Matlacha and about a 10 minute ride to The pine Island sound which gives you access to other islands such as North Captiva , Cayo Costa and Boca Grande to name a few. You can fish off the dock or just sit and enjoy the beauty of the water.brbrThere is a gate that separates the front and back yards, and a outdoor shower next to the pool at the rear of the house. There is a private boat launch which guests will have access to less than two blocks away from the house. Also the Pine Island Marina less than 10 minutes away for launching larger boats or keeping them there. There is also the Monroe Canal Marina 14 mins from the house. They offer lots of goods and bait for purchase as well as boat rentals.brbrFeel like visiting other islands but don't feel like renting a boat to do it, you can always use the Island Girl Charters to ferry you over to North Captiva and adjacent islands, or book your own private charter to explore the area. It's located less than 10mins from the house.brbrMinutes away from a newly built Publix for all your grocery needs. Also minutes away from various shops and restaurants on matlacha. Less than 15 minutes to St. James City on the south end of the island. With numerous delicious restaurants and bars along the way.brbrPine Island offers alot of amenities ... Everything from amazing breakfast spots and local art...to goat yoga and beautiful walking trails, and Pine Island is very dog friendly. Dogs are allowed at most places with an outside patio...some restaurants even have a separate menu for your four legged family member. brbrIf fishing is your game .. well look no further. The water around Pine Island is a great place to reel in your next trophy catch. Some of the local restaurants will even cook it for you. There's plenty of great charter outfits to choose from on the island as well.brbrA short drive from the house. There is The Alden Pines Country Club That is an 18-hole golf course and open to the public.brbrThere is fine dining on the north end of the island at The Tarpon Inn. Fantastic breakfast at The Perfect Cup, great food from Phuzzy's Boat Shack , Miceli's and many more, and lots of the restaurants have live music and are perfect spots to sit by the water and hang out.brbrMatlacha is home to some adorable boutique shops and art galleries for some local shopping. brbrThere is a reason why when people move to Pine Island or visit they fall in love with it. The people are friendly, the island is beautiful and it has a relaxing no worries feel to it. It's also surrounded by other islands and the mainland making it very protected from bad weather. brbrThis beautiful home is named after my mother Shirley who was a firm believer that if you do good things in life then good things will come to you and you'll be surely blessed in your life. With how peaceful and beautiful the house is and the memories that will be made here with family and friends.... One could say you'll be Shirley Blessed. brbrFrom Punta Gorda airport it's about a 35 minute drive... And if you're flying in to Fort Myers airport it's roughly a 45-minute drive to the house. Read More

  • Property-2 Image 1
    Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal
    Private Vacation Home $130 / Nightly
    • (3) Exceptional
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    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!brbrOur 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. brbrThere are several community boat ramps just minutes away and we have plenty of driveway parking area for storing a trailer. brbrEnjoy 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. brbrEnjoy Cable TV, wify internet, 2 bicycles, two Kayaks, a gas grill, ample parking and lower level covered patio. brbrYou are only minutes from the Philips community park with its pool and tennis courts.brbrPine Island is encircled by world-class fishing waters, the beaches of Ft. Myers, Sanibel Island and Captiva, all within a quick drive or quicker boat ride. brbrExplore Pine Island, nearby Matlacha, and St. James City, with their many shops and restaurants.brbrTake a water taxi from Pine Island to Cabbage Key and Cayo Costa beaches to avoid the crowds and enjoy some of the best shelling there is. It’s also easy to rent boats and arrange fishing charters nearby.brbrWe have an exterior ring camera only in operation when no guests are on the premises, so doorbell will not be operational during your stay. br Read More

  • Property-3 Image 1
    Florida Island Paradise Home, Bokeelia Canal, Pine Island, w/Pool & Boat Lift
    Private Vacation Home $275 / Nightly
    • (9) Exceptional
    • 3 Bed
    • 3 Baths
    Bokeelia, Florida, United States

    We are very happy to report that we were not impacted by Hurricane Ian! This beautiful 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, dishes, cups and silverware, 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. brbrPine Island is world renown for fishing, boating and kayaking. Tarpon, Grouper, Reds, all here! Cayo Costa, Captiva, Boca Grande, Charlotte Harbor, Shell Pass, and Pine Island Sound are only minutes away by boat. brbrEnjoy a delicious meal and at one of the many waterfront restaurants. Shop the charming boutiques and galleries in Matlacha. Take a bike ride on the designated bike path that extends the 17 mile length of Pine Island. br Explore The Great Calusa Blueway Paddling Trail (check out www.paddleflorida.net), a 190-mile marked canoe and kayak trail that meanders through the coastal waters and inland tributaries of Lee County. Lavender's Landing Boat Ramp is a block away, easy kayak launch and access to The Paddling Trail. brVisit the many protected wildlife preserves on Pine Island, to see the native pines, bald eagles and tropical groves. Guide yourself through the 3/4 mile Calusa Heritage trail, take a trip to The Museum of The Islands. Acres of mango tree farms, indulge in a fresh delicious mango smoothie or homemade mango jam.brbrJug Creek Marina and Fish House, The Lazy Flamingo 3 Restaurant and Marina and the pier at Captain Capt'n Con's Fish House are nearby, enjoy dining, fishing, and gorgeous sunrises and sunsets. The casual Lazy Flamingo Restaurant, overlooking the harbor at Four Winds Marina is a favorite spot to relax and have fun whether you are just off your boat, or out for a night on the town. Bring your fresh catch and have the chef prepare it your favorite way. Wave hello to "Uno", the resident dolphin who loves to pose for pictures! brbrPlaces nearby to visit include Cape Coral, Fort Meyers, Punta Gorda, Sanibel, and Naples for theater, concerts, art, and dining. Welcome to Bokeelia and Pine Island Paradise! Please note cameras are placed at the front and back yards and dock area. Read More

  • Property-4 Image 1
    First-Floor, Snowbird-Friendly Townhouse w/ Shared Pool, WiFi, Central AC, & W/D
    Private Vacation Home $158 / Nightly
    • (4)
    • 2 Bed
    • 3 Baths
    Bokeelia, Florida, United States

    Mermaid Haven at BocillabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'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! 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 and tennis court 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.brbrThings to KnowbrFree WiFibrFull kitchen with a dishwasherbrThe living room sofabed provides an extra sleeping spacebr*This condo does not have a boat slip. There is a community dock where guests can fishbrWorld class tarpon fishing is available in the area, as well as flats fishing for Redfish and SnookbrJug Creek is home to an abundance of wildlife, including birds, turtles, manatees, dolphin, and fishbrSnowbird-friendlybrbrParking notes: All condos come with one (marked) parking space directly under the condo. There are shared visitor spaces, which are first come, first served. A maximum of two vehicles are allowed by any single condo. Overhead clearance for parking under buildings G and H is approximately six-and-a-half feet.brbrThis rental is located on floor 1.brbrDock details: This condo does not have a boat slip. There is a community dock where guests can fish. · Boat launch, boat and trailer parking and wet storage is available within 0.5 miles (Bokeelia Fishing Pier and Boat Ramp (next to Capt’n Cons). Boat launch and parking is also available at Pineland (4 miles). brBoat rental is available at Four Winds Marina (1.0 miles). Boat charters located on site, and within a few miles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page. Read More

  • Property-5 Image 1
    The Bokeelia Boathouse, waterfront, Boat Dock, Pine Island, Florida
    Villa $292 / Nightly
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Paradise awaits you at our recently renovated island get away home.brbrLocated on the water in Bokeelia on Pine Island we are a world away from the everyday with Fort Myers and Cape Coral within easy reach when you need them.brbrKnown as a fisherman's paradise Bokeelia offers some of the best fishing waters around.brbrOur two bedroom home offers two king size beds and a sofa, sleeping a maximum of 6 people.brbrOur home is designed with your comfort in mind while the spacious floor plan and screened in porch area allow you to enjoy the breathtaking views of the water.brbrDock your boat at the house with plenty of parking area for storing your trailer, a community boat ramp is right around the corner.brbrIsland style living, plantation shutters, ceiling fans, casual comfort, we invite you to come and recharge at our home away from home.brbrWe will be happy to assist you with the planning of your vacation. Whether it be a fishing charter, shelling or sightseeing tour, sunset cruise, dinner reservations, chef to cater for you and your friends or just where to buy the best book for doing nothing at allbr Read More

  • Property-6 Image 1
    2/2 IN BOKEELIA WITH AMAZING GULF ACCESS! BOAT LIFT INCLUDED!
    Private Vacation Home $286 / Nightly
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    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.br brbrProperty Features:br • Boat lift, 10,000 lbbr • Great dock for fishingbr • All towels and linens are providedbr • Smoke-free br • Complimentary high speed wireless internetbr • Fully equipped kitchenbr • Parking for Boat Trailer br • Queen blow up mattress Read More

  • Property-7 Image 1
    Bokeelia Retreat - Fishing Docks & Canals Nearby!
    Private Vacation Home $305 / Nightly
    • (14)
    • 3 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Prepare for rest and relaxation when you book a stay at this 3-bedroom, 2-bathroom vacation rental home in Bokeelia! Located near fishing docks, canals, and a boat ramp, this home boasts a fully equipped kitchen, a bonus room perfect for game nights, and a spacious backyard. Bring your kayaks or boat along and enjoy days of exploration on the canals or head into Cape Coral for a beach day. Return to your home-away-from-home for a freshly cooked meal and to watch the sunset with your loved ones!brbr-- THE PROPERTY --brbr1,375 Sq Ft | Large & Spacious Yard | Bonus Room w/ Foosball Table | Boat Ramp NearbybrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full BedbrbrHOME FEATURES: 2 flat-screen TVs, washer & dryer, dining table, breakfast bar w/ seating, board games, beach towels & chairsbrKITCHEN: Dishwasher, cooking basics & spices, drip coffee maker, coffee grinder, Crockpot, toaster, knife set, dishware & flatwarebrGENERAL: Free WiFi, central A/C, complimentary toiletries, linens & towels, trash bags & paper towels, hair dryer, hangers, self check-inbrFAQ: Step-free accessbrPARKING: Garage (2 vehicles), driveway (2 vehicles), boat parkingbrbr-- THE LOCATION --brbrON THE WATER: Lavenders Landing Boat Ramp (0.2 miles), Bokeelia Fishing Pier (1.5 miles), Matlacha Pass Bridge (9.9 miles), Pine Island Sound Aquatic Preserve (10.0 miles), Matlacha Pass Aquatic Preserve (10.5 miles), Yacht Club Public Beach (23.3 miles)brIN NATURE: Pine Island Flatwoods Preserve (10.9 miles), Galt Preserve (13.9 miles), Four Mile Cove Ecological Reserve (21.8 miles), Charlotte Harbor Preserve State Park (28.2 miles)brTOUR THE AREA: Pine Island Boat Tours (0.6 miles), Tropic Star of Pine Island (2.5 miles), Tarpoons Tours (6.1 miles)brAIRPORT: Southwest Florida International Airport (38.1 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The clothesline is not available for guest use Read More

  • Property-8 Image 1
    NEW!! The “WATERSIDE” COTTAGE~With dockage
    Private Vacation Home $255 / Nightly
    • (34) Exceptional
    • 1 Bed
    • 1 Baths
    Bokeelia, Florida, United States

    World class tarpon fishing, superb flats fishing for reds, & Snook in the mangroves, Trout in the grass, giant Sharks in the pass, Mackerel in the harbor, Grouper on the wrecks. You can catch Sheephead and Mangrove snapper right off the sea wall out behind this cottage. This cottage has quick access to Shell Pass, Pine Island sound, Charlotte Harbor. There are beautiful sunrises and sunsets, and great kayaking in the area. brbrThe golf carts/kayaks/boats/bikes are available to rent through a local resources! Golf cart approved areas make it a fun addition to the trip! Bike ride the entire island and stop for lunch or views! Kayaking this area is voted as one of the top spots and boating and fishing, what can I say.. both amazing off this island! brbrWait till you see this freshly done cottage! Ready for your stay, bring your boat or rent one near by to dock here. Or, simply enjoy sitting by the water with a cup of coffee. New mini split a/c just installed to keep you comfortable on even the hottest of days! Lots of history on this beautiful island with fishing you'll be amazed with! Tarpon capital of the world and Charlotte Harbor moments away from the dock! Boca Grande, Cayo Costa, Useppa, North Captive, Sanibel and Cabbage Key, etc. a short boat ride away! The dock is a shared dock. Occasionally, I have guests from other cottages that may need dockage. These guests are asked to load and unload only. brbrI have several properties all located next to one another for family or friends to vacation together yet have their own space.brbrAll properties have WIFI, locals channels and ROKU.brbrOther properties:brbrThe Lookout Cottage Property ID# 7371979 Bokeelia brbrThe Quarterdeck Cottage Property ID# 4539791 Bokeelia brbrThe Dockside Cottage Property ID# 9462163 St James CitybrbrPlease check all four properties! All unique and beautifully decorated! Read More

  • Property-9 Image 1
    House located in Alden Pines on Pine Island
    Private Vacation Home $199 / Nightly
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Charming two-bedroom home on Alden Pines Golf Course. This home has a fireplace, a spacious back porch, two bedrooms, and two baths. It is located on the 16th hole and has a freshwater lake in the backyard. It sits on a nicely landscaped large lot. Renters have access to the Alden Pines Country Club golf course for a reasonable fee and the pool at The Tarpon Lodge. Boat lovers can also discuss boat slip availability at an extra nightly charge with the office staff of the Tarpon Lodge. Read More

  • Property-10 Image 1
    Unique Charlotte Harbor experience on a comfortable Schucker 436 trawler.
    House Boat $220 / Nightly
    • 2 Bed
    • 1 Baths
    Bokeelia, Florida, United States

    Boaters Only at this time. I want to welcome boaters to an experience of a lifetime! You must have a boat that you can bring in order to access "Namaste" and to travel to and from your car at the dock.brFor the past year, I have restored this classic Schucker 438 Trawler and prepared her for cruising in the Caribbean. The main sleeping berth is in the open main salon with a pull out bed in the upper cabin. It is comfortable and roomy with the best 360 degree nature view that you are likely to ever find. This experience is only available to boaters at this time. If you are experienced with single kayaks, I have two that can be used for your transportation to and from the boat. That option is a poor substitute for bringing your own boat as a support vessel for transportation. brThis is not your typical rental room. It is an actual boat that is anchored approximately 100 yards off shore and not at a marina. You should provide your own boat to get to Namaste and to return to shore where your car and trailer may be stored on a nightly basis at Knights Marina. ($10 per car plus $5 per trailer. ) This boating experience requires that you receive instructions to insure your safety and enjoyment. We hope that you will experience the peaceful feeling of sleeping on the boat, and immerse yourself in the natural beauty of Charlotte Harbor. Read More

  • Property-11 Image 1
    The Shell Shack 2/2 in Bokeelia with Boat Lift & Boat Ramp on Site with
    Private Vacation Home $345 / Nightly
    • (1) Exceptional
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Slip away to a quiet place located north on Pine Island. Bokeelia, Florida is home to some of the worlds best fishing grounds, and it's all at your fingertips when you stay in this immaculate 2 bedroom 2 bath waterfront. This property has two separate spaces. 1 bedroom, 1 bath located on the ground floor and the other 1/1 on the second floor. Two amazing spaces to enjoy some relaxtion. The lower level lanai offers a screened in outside living area. The porch upstairs is great to enjoy your morning coffee or watch the boats stroll in. You will sure feel like your on "Island Time" with the island decor. Bring your boat! Boat ramp is conveniently located on property for easy boat or kayak drop in.  WATER LOCATION LOCATION LOCATION! This property is located on a canal with incredible Gulf access. You are mere moments from Charlotte Harbor, Pine Island Sound, and Matlacha Pass.  Trout, Snook, Redfish, Grouper, and Tarpon are just some of the fish you will find nibbling at your line.  It is less than 5 miles to world renowned Boca Grande Pass, home to some of the worlds most active tarpon fishing tournaments.  brbr*BOAT LIFT IS NOW AVAILABLE! br**PROPERTY IS FOR SALE, A 24 HOUR SHOWING NOTICE MAY BE REQUIRED. br  Read More

  • Property-12 Image 1
    Well Equipped Pet/Smoke Free Family Home - bring your boat!
    Private Vacation Home $346 / Nightly
    • (13) Exceptional
    • 2 Bed
    • 3 Baths
    Bokeelia, Florida, United States

    WE DON'T LIVE IN A SQUARE WORLD, WHY VACATION IN A SQUARE HOUSE?brCome and experience the unique feel of a round house designed and built by world renowned Deltec Home, Inc., of Asheville, NC. This 2 story home, built on pilings, comfortably sleeps 6 with 2 bedrooms and 3 full baths, washer/dryer and a queen sleeper sofa all located on the first floor. The second floor contains a fully equipped kitchen, dining room and a full bathroom. Smart TV in the Living Room, streaming available also in the bedrooms (no cable). From the 2nd story deck you will enjoy beautiful sunsets and see for miles with views of Charlotte Harbour in the distance. A large secured storage area is provided below the home for your convenience. From the hardwood floors, flat screen TV's, granite countertops to the ceiling fans, you will find this home to have a classy yet very comfortable feel.brThis Bokeelia home, located on 1.3 acres, is within walking distance to Four Winds Marina, where you can rent or store your boat while you're here. There is NO DOCKAGE available at our home.brYou can also grab lunch or dinner at The Lazy Flamingo. A public boat ramp and fishing pier are less than a mile from the property. Bokeelia is a quiet, relaxed and tranquil spot which will remind you of what island life in Florida once was. The waters surrounding Bokeelia offer some of the best fishing in the country. You can stay in the back bays and fish for snook, redfish or snapper or head to the flats for trout and mackerel or try your hand at tarpon fishing in the famous Boca Grande Pass. Visit up close with the dolphins from the canoe. For land lovers, the island offers fine and casual dining, golf, swimming, tennis, biking, and shopping. it is just a short 30 minute ride off the island to enjoy historical landmarks (The Edison Home), a family water park (SunSplash), catch a show at the Broadway Palm Dinner Theater or shop at one of several malls in Fort Myers.brWe have bikes, tennis racquets, volleyball, golf clubs, a canoe, and much more to help make your stay enjoyable. Please note...NO pets are allowed! Read More

  • Property-13 Image 1
    Puffy’s Palace
    Private Vacation Home Select Dates for Price
    • 3 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Our three-bedroom, 2 bath, completely updated home is in Alden Pines Golf & Country Club. Alden Pines is an 18-hole golf course in a natural setting. Pine Island has abundant wildlife at most anytime you can look up and see, osprey, bald eagles, blue herons, snowy-white egrets, and wood storks.brbrPine Island does NOT have a beach, you can take a water taxi to one of the beaches or drive off the Island but there is plenty of fishing. Fish off the Matlacha Drawbridge, the MOST fished bridge in South West Florida. Hire a fishing guide or bring your boat and put in at the Pineland Marina. Almost all the restaurants on Pine Island will cook your fish anyway you request. Take a water taxi, cruise/tour boats to the islands of Cabbage Key, & Cayo Costa. Stop for lunch at the islands of Cabbage Key, Captiva, Sanibel or Upper Captiva.brbrIt’s a kayak lovers paradise, Pine Island is the largest island (17 miles long and 2 miles wide) on the west coast of Florida, just 20 minutes from Cape Coral, 30 mins from Fort Myers and one hour from Fort Myers Airport. FLORIDA’S BEST KEPT SECRET, untouched southern Florida is quaint, quiet, fringed with mangroves rather than white sandy beaches. Enjoy kayaking in the sheltered waters of Matlacha Pass and the Pine Island Sound Aquatic Preserve. brbrBring your bikes there is a bike trail from one end of the island to the other. Tennis and pool at the community center, is a short bike ride, only 5 miles and play on 4 new courts. You can play at night. There is a round robin every Monday, Wednesday, and Friday from 9 - 11 that anyone can jump in. All are welcome! There is a league that plays Tuesdays and Thursdays, but they don’t use all the courts and they are done by 11am. Recently added is pickleball.brbrOn Pine Island, check out the local shops in Matlacha, dine and relax at the many waterfront restaurants, specializing in fresh seafood, served up with a casual, low-key, island atmosphere.brbrMy most favorite thing to do is pack up the golf cart, bring a camera, cheese & crackers, beer-wine-or martinis, and go to the Pine Island Marina and watch the sun set. Do this every night you will not be disappointed. Read More

  • Property-14 Image 1
    Brand new Romantic ground floor waterfront getaway
    Private Vacation Home $200 / Nightly
    • (9)
    • 1 Bed
    • 1 Baths
    Bokeelia, Florida, United States

    BRAND NEW - Amazing, 1 bedroom waterfront suite. This suite is on par with a first-class hotel room in a major city.brWalkout to the backyard, which is ready for your boat at the backyard doc. Kayak is onsite.brThis unit can be paired up with a 2 bedroom if you need additional space. Read More

  • Property-15 Image 1
    Bokeelia Charming Island House
    Private Vacation Home $150 / Nightly
    • (8) Exceptional
    • 3 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    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. Read More

  • Property-16 Image 1
    Waterfront condo located in the waterfront paradise of Bokeelia
    Condo $245 / Nightly
    • (5) Exceptional
    • 2 Bed
    • 3 Baths
    Bokeelia, Florida, United States

    Incredible waterfront views in this fully stocked Bocilla Island Club condominium. This is an end unit which gives a panoramic view of the harbor. The development includes two heated pools, tennis courts, a small marina, a private pier on Charlotte Harbor, and lots of privacy. The condo is of stilt construction with the first floor being under building parking, the second floor being the kitchen and living area, and the third floor being the two bedrooms and two full baths along with the laundry room. If you love the water and a lazy island atmosphere, 'Lazy Harbor' is the place for you. The condo also comes with two kayaks to explore Jug Creek and Charlotte Harbor. We have made lots of upgrades including new flooring throughout, new mattresses, new shiplap wall, new paint throughout, and a 65" smart TV + TV's in each bedroom. Fully painted in June 2022 (not all pictures reflect new paint). As a bonus, there is a "pet" dolphin that makes daily visits in the harbor and in the canal! A boat lift is available for a maximum 24' boat. NOTE: THERE IS NO TRAILER PARKING ALLOWED IN THE DEVELOPMENT. RENTER IS RESPONSIBLE FOR FINDING A PLACE TO STORE YOUR TRAILER. REACH OUT TO BOKEELIA PIER AND BOAT RAMP FOR POTENTIAL OPTIONS. Most repairs have been made to the development following Hurricane Ian with the exception of the pier on Charlotte Harbor. Read More

  • Property-17 Image 1
    Island Paradise Get-Away
    Private Vacation Home $124 / Nightly
    • 2 Bed
    • 1 Baths
    Bokeelia, Florida, United States

    Welcome to your Pine Island get-away! This recently updated 2/1 home has all you need for a perfect relaxcation. Bedroom one has a queen bed and TV, bedroom 2 has two twin beds. Plenty of parking for your boat and trailer. Use of a boat lift on a nearby canal possibly available at the time of your reservation, ask for details. Close to fishing piers and marinas, (Jug Creek and Four Winds Marinas) you can enjoy world class fishing, boating, and kayaking. This family friendly Island has paved walking and biking paths, nature preserves, and beautiful palm and mango farms. The waterways of Matlacha Pass and the Pine Island Aquatic Preserve are excellent for kayaking and canoeing and are a haven for birdwatchers and nature lovers. Lots of boat charters are available for fishing and party cruises. Enjoy a beautiful sunset at one of many waterfront restaurants such as Tarpon Lodge, Cap'n Cons or Lazy Flamingo while sipping your favorite adult beverage. See why Pine Island is one of Florida's best-kept-secret destinations!brCayo Costa State Park is a quick trip by boat or ferry. Visit nearby Cape Coral and Fort Myers for even more sun worshipping and beach combing. We are pet friendly. br Read More

  • Property-18 Image 1
    Dog-Friendly, Canal-Front Home with Canal Access, Central AC, and WiFi
    Private Vacation Home $96 / Nightly
    • (1)
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Flamingo BungalowbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrOld Florida meets modern comfort and convenience in this charming Bokeelia home. There’s a homey feel from the moment you step through the front door into the first of two comfortable seating areas, each with beachy touches, plenty of seating and flatscreen TVs with streaming capabilities. The main living room and kitchen share an open living area, so the chef won’t feel left out while whipping up anything from a snack to a full meal in the well-appointed space. Outside, through your sliding glass doors, you’ll find a fully-enclosed sun room, a perfect space for reading a book or listening to music on the sound dock.Once you settle in, it's time to explore. Take a turn around charming Bokeelia on one of the two bikes available for your use, or hop on one of the home's paddleboards and take to the water. When you return, grab a tasty beverage and head out to your canal-front deck to watch the stars come out. brbrbrThings to Know:brDog-friendlybrSnowbird-friendlybrFree WiFibrStreaming available with guest's accountbrTrundle bed in the sitting area and another in the Florida roombrbrIf you are bringing a dog on your trip, the nightly pet fee is already included in your quote when selecting 'Yes' to pets. If you would like to add more dogs, please contact us. The $20 nightly fee will apply for each additional dog.brbrParking notes: Two cars can fit onto the driveway. Parking is not allowed on the street or gravel. brbrDock details: Boat lift is not for guest use. Guests can stand, sit, or fish on the dock. Due to multiple factors beyond Vacasa's control, we cannot guarantee a safe docking of any water crafts.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page. Read More

  • Property-19 Image 1
    Spectacular Waterfront! Minutes to Charlotte Harbor Bring Boat Free Kayak!????
    Private Vacation Home $220 / Nightly
    • (25)
    • 2 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    Spring Break Discounts!! Limited March & April 2023 vacancies left. Hurry! Booking quickly!! No hurricane damage. Beaches, marinas, gas stations, restaurants, & grocery stores are all open for business.brbrKayakers, fishing enthusiasts, bird watchers, & nature lovers...brbrWelcome to Docktales & Dreams!!! ?br2 person kayak & life jackets included! ?(use at your own risk)brTarpon Fishing Capital of the World!! ?brBrand new 60 ft dock! Bring your boat! ??brEasy run out to Charlotte Harbor, Boca Grande Pass, & Gasparilla Island. brbr Sit on the dock, close your eyes, & just listen.... The incredible sounds of nature will surround & captivate you. Now, open your eyes & take it all in. You will be transported back to a wonderful place in time where living life was more important than anything else! This is Docktales & Dreams! brFrom the moment you arrive, you will be captivated by the beauty, tranquility & serenity this lovely, very clean 2/2 direct gulf access home has to offer. Enjoy your cup of coffee or happy hour drink on the porch overlooking the wide natural canal & new dock! Take the kayak out & enjoy the sights & sounds of mullet jumping out of the water, see the playful dolphins & manatees swimming by, or spot the numerous ospreys, bald eagles, egrets, blue herons, ibis, spoonbills & woodpeckers flying overhead. Take your boat out the marked channel with no fixed bridges & enjoy the amazing fishing or explore all of what Pine Island & Southwest Florida have to offer, including Cayo Costa, Cabbage Key, Sanibel & Captiva Islands. When you return, feel free to tie it off the dock. The dock will accommodate a boat up to 28 ft. Or cast a lazy line off the dock to see what bites. Snook, trout & tarpon have been caught right off the dock! You will feel miles away from it all, but you are only 3 minutes from the grocery store & minutes away from the historic Tarpon Lodge, Matlacha, St. James City, & great local waterfront restaurants. brbrExtensive upgrades & renovations made including:brBrand new kitchen, floors & guest bathroom. Newer a/c, new refrigerator/freezer, new dryer, newer master bathroom, new mattresses, new furniture, new ceiling fans, new dock, new outdoor cushions, new landscape lighting, etc.brbrbrWeekly/Monthly discounts available (Excluding Holidays)brHurry, filling up fast.brbrAll inquiries will be considered.brbrGarage & boat lift are not for guests' use.brOwner does not assume liability for kayak use. Guests must have experience with kayaks.brProperty not suitable for children under 8.brbrbrbrbrbrbrbr Read More

  • Property-20 Image 1
    Historic Florida "Cracker Cottage"
    Agritourism $186 / Nightly
    • (1) Exceptional
    • 3 Bed
    • 2 Baths
    Bokeelia, Florida, United States

    NO DAMAGE FROM HURRICANE IAN!!!!! Beautiful historic property located in quaint Bokeelia, Florida. Close to boat ramps, kayak launches and restaurants, but in the country with amazing views of the stars! Contact me for discount on long-term rental if you need an idyllic place to stay while rebuilding. Read More

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Information about vacation rentals in Bokeelia

houseNumber of available properties in a Bokeelia

76 properties

pricePrices starting from

$58.00

petsNumber of properties with pets allowed

28 properties

spaNumber of properties with pool/spa

40 properties

kidsNumber of Children welcome properties

64 properties

beachNumber of properties near beach/ocean

30 properties

Most popular vacation rentals in Bokeelia

  • thumb
    $ 129.00 avg/night
    13
    • 3 Beds
    • 3 Baths
    • 8 Guest(s)
    Beautiful "Old Florida" Pine Island Golf Course & Marina Home Bokeelia, Florida, United States

    This is a lovely, updated 4/3 stilt home located directly on the Alden Pines Golf Course and only... Read More

  • thumb
    $ 203.00 avg/night
    22
    • 2 Beds
    • 2 Baths
    • 6 Guest(s)
    Paradise just waiting for you! Bokeelia, Florida, United States

    If you are looking for an awesome get-a-way, we have the place for you! If you love to fish,... Read More

  • thumb
    $ 345.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    The Shell Shack 2/2 in Bokeelia with Boat Lift & Boat Ramp on Site with Bokeelia, Florida, United States

    Slip away to a quiet place located north on Pine Island. Bokeelia, Florida is home to some of the... Read More

  • thumb
    $ 110.00 avg/night
    1
    • 3 Beds
    • 2 Baths
    • 6 Guest(s)
    Private Hideaway in Pine Island community Pool and Marina a few steps away. Bokeelia, Florida, United States

    This is my personal dream getaway I’m newly sharing with avid travelers looking to escape their... Read More

  • thumb
    $ 150.00 avg/night
    8
    • 3 Beds
    • 2 Baths
    • 6 Guest(s)
    Bokeelia Charming Island House Bokeelia, Florida, United States

    Welcome to your getaway home- a newly remodeled spacious 3 beds 2 bath house, the left side unit... Read More

  • thumb
    $ 198.00 avg/night
    23
    • 2 Beds
    • 3 Baths
    • 4 Guest(s)
    NEW! THE LOOKOUT COTTAGE~BOKEELIA ~PINE ISLAND FL With dockage across the street Bokeelia, Florida, United States

    Beautiful and newly updated "Old Florida Cottage" just waiting for you to enjoy! Once on Fort... Read More

  • thumb
    $ 306.00 avg/night
    4
    • 3 Beds
    • 4 Baths
    • 6 Guest(s)
    Beautiful waterfront Key West style home with a pool Bokeelia, Florida, United States

    Private, spacious Key West style home located on a canal with quick access to the pine Island... Read More

  • thumb
    $ 255.00 avg/night
    34
    • 1 Beds
    • 1 Baths
    • 2 Guest(s)
    NEW!! The “WATERSIDE” COTTAGE~With dockage Bokeelia, Florida, United States

    World class tarpon fishing, superb flats fishing for reds, & Snook in the mangroves, Trout in the... Read More

  • thumb
    $ 275.00 avg/night
    9
    • 3 Beds
    • 3 Baths
    • 6 Guest(s)
    Florida Island Paradise Home, Bokeelia Canal, Pine Island, w/Pool & Boat Lift Bokeelia, Florida, United States

    We are very happy to report that we were not impacted by Hurricane Ian! This beautiful 3 BR, 3... Read More

  • thumb
    $ 245.00 avg/night
    5
    • 2 Beds
    • 3 Baths
    • 6 Guest(s)
    Waterfront condo located in the waterfront paradise of Bokeelia Bokeelia, Florida, United States

    Incredible waterfront views in this fully stocked Bocilla Island Club condominium. This is an end... Read More

 

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