Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $540 per night (USD)
VRBO
Perfect Placement, Post Renovation Photos Coming Soon
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home (sleeps 6 adults and 4 children) is extremely close to the ocean and a Florida sugar sand beach whic ...
From $540 per night (USD)VRBO
- From $865 per night (USD)
VRBO
New luxury pool home, 2 min to beach, 360 water views, club available
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 19
Overview of the property: • Sublime is a brand new, stunning 3,200 square foot, 7-bedroom, 6-bathroom, luxury beach hom ...
From $865 per night (USD)VRBO
- From $500 per night (USD)
VRBO
The Pearl Beach House, North Captiva Island, FL | Enhanced cleaning measures
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This water-front property offers designer furniture and panoramic views throughout. Experience unprecedented privacy wit ...
From $500 per night (USD)VRBO
- From $155 per night (USD)
VRBO
CASTAWAY in MATLACHA on deep water canal with BOAT DOCK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are opening up our house to let more people like YOU enjoy our Florida PARADISE. This is truly Florida's Best Kept ...
From $155 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you are looking to get away from it all and surround yourself in Florida's tropical nature then Pine Island is the pl ...
From $130 per night (USD)VRBO
- From $488 per night (USD)
VRBO
STEPS TO THE BEACH - Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
* ISLAND ACCESSED BY FERRY ONLY LANIKAI is a 2 bedroom, 2 bath house only steps from the beach, with a private heated p ...
From $488 per night (USD)VRBO
- From $160 per night (USD)
VRBO
SEASIDE VILLA DESTIN - In the heart of Pine island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our SEASIDE VILLA DESTIN is idyllically located on Pine Island, which is situated in front of Cape Coral. Especially for ...
From $160 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Florida Island Paradise Home, Bokeelia Canal, Pine Island, w\/Pool & Boat Lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Time Inn! This 3 BR, 3 bath private home is located in Bokeelia Isles, Pine Island, Florida. Welcome ...
From $275 per night (USD)VRBO
- From $305 per night (USD)
VRBO
3-story Pool Home w\/Conservatory has 360 panoramic views\/180’ of dock\/Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This home is “All Decked Out” and exemplifies Florida Coastal living with complete 360* views of Pine Island Sound from ...
From $305 per night (USD)VRBO
- From $817 per night (USD)
VRBO
Private beach access ! Best outdoor area w\/ boat bar, pool, 360 rooftop views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
5 Star Property. We are located on the northern tip of North Captiva Island, with lots of privacy away from the crowds ...
From $817 per night (USD)VRBO
- From $165 per night (USD)
VRBO
13) Wake Up on the Water in St. James
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience waterfront serenity at our 2-bed, 2-bath St. James City home. Relax in the cozy living spaces, savoring tranq ...
From $165 per night (USD)VRBO
- From $225 per night (USD)
VRBO
12) Waterfront Escape in St. James
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to our inviting 3-bedroom, 2-bathroom home in charming St. James City, Florida. Located in a serene waterfront co ...
From $225 per night (USD)VRBO
- From $899 per night (USD)
VRBO
Flip Flops BEACH FRONT house and Sand Bar. \nMajestic panoramic views and sunsets
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful 2 story beach front house with ground floor Patio and Sand Bar. Home is located on the exclusive North Captiva ...
From $899 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Quick access to the Gulf of Mexico!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A nice, cozy 2 bedroom, 2 bath waterfront home located in St James City, Florida. The home has its own boat lift to use ...
From $190 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Studio#1-Back Bay Sunsets in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take it easy at this unique and tranquil open water getaway - perfect for the solo traveler or a couple. Oversized close ...
From $119 per night (USD)VRBO
- From $118 per night (USD)
Expedia
Waterfront, Island Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Waterfront community of St James Isle in St James City. 2 bedroom 2 baths with large great room & large master bedro ...
From $118 per night (USD)Expedia
- From $162 per night (USD)
VRBO
Stylish Bokeelia Home: Deck & Outdoor Dining Area!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Break away from your routine and book it to this 2-bedroom, 2-bath Bokeelia vacation rental! The well-equipped and welco ...
From $162 per night (USD)VRBO
- From $388 per night (USD)
Expedia
3\/3 Gorgeous Pool Home, Bay Front!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom two bathroom fully upgraded GORGEOUS property sits right on the bay. Water views are endless! This house o ...
From $388 per night (USD)Expedia
- From $103 per night (USD)
VRBO
Single-Story Home in Bokeelia: Pets Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Seeking a coastal adventure filled with sunshine and good times? Look no further than this 2-bedroom, 1-bathroom vacatio ...
From $103 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Beautiful waterfront condo on main canal, heated pool and boat space available
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**JUST PURCHASED, NEWLY AVAILABLE FOR RENT, 30 day minimum** You're on Island Time! This beautifully updated waterfront ...
From $150 per night (USD)VRBO
- From $953 per night (USD)
VRBO
Escape to CASA PALMA HIDEAWAY! 4BD\/3BA, Pool, Outdoor Kitchen, boat slip & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This enchanting 4-bedroom, 3-bathroom retreat is a harmony of comfort and luxury, promising an unforgettable escape. On ...
From $953 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Island Cottage in Bokeelia - close to fishing and water sports!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom/one bath island cottage close to public boat ramp; fishing dock and marina. Down the street from kayak and p ...
From $125 per night (USD)Expedia
- From $168 per night (USD)
VRBO
Amazing Stay in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully renovated studio has everything you need for a fabulous stay in Matlacha. It is located on a quiet/peac ...
From $168 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Off the Charts Inn King Efficiency
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Experience the epitome of luxury with our King Efficiency suite. Indulge in the grandeur of a spacious king bed, a cozy ...
From $186 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Spacious \"Crab Cakes\" Cottage on beautiful North Captiva Island,FL with GolfCart
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Crab Cakes Cottage on North Captiva Island, your perfect getaway destination! Nestled on a tranquil street, j ...
From $334 per night (USD)VRBO
- From $208 per night (USD)
Expedia
Off the Charts Inn - King Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate luxury in our expansive King Suite! Indulge yourself in the grandeur of a king-sized bed, comple ...
From $208 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Off the Charts Inn - Standard Queen room
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Immerse yourself in the sheer bliss of this spacious haven, complete with a fully equipped kitchen for your convenience. ...
From $186 per night (USD)VRBO
- From $197 per night (USD)
Expedia
Off the Charts Inn - Queen Double Room
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Experience the ultimate comfort and luxury in our expansive Queen double bed room! Immerse yourself in the sheer bliss o ...
From $197 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Pet friendly 3 bedroom, 2 bath pool home with direct access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this pet-friendly home, eagerly awaiting your arrival. With three bedrooms and two full baths, it provides a ...
From $214 per night (USD)VRBO
- From $222 per night (USD)
Expedia
Cozy home in Matlacha on the water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
comfy 2 bedroom 2 bathroom house in matlacha. House has beautiful kitchen and bathrooms. This home also is on the water ...
From $222 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Island Getaway, with boat ramp access nearby. You can park your boat on property
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relaxing is an understatement. Perfect island getaway from the city. It's good for retirees to families. Island culture ...
From $195 per night (USD)VRBO
- From $160 per night (USD)
Expedia
2-bedroom waterfront home with gulf access and close to bars and restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the entire family at our peaceful getaway. Enjoy nature at its finest, as you might be greeted by manatees, d ...
From $160 per night (USD)Expedia
- From $649 per night (USD)
VRBO
Sunning Gulf Views! Pool and Endless Entertainment
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower, Fat-Tire Bikes+ 🏖️St ...
From $649 per night (USD)VRBO
- From $90 per night (USD)
Expedia
A little piece of paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Indulge yourself in beautiful sunsets and the peaceful island life in this one bedroom, one bathroom mobile home just m ...
From $90 per night (USD)Expedia
- From $163 per night (USD)
VRBO
Blue Lagoon: Beautiful Canal Front Home in Charming Matlacha, FL community!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Update following Hurricane Ian: This home sustained minimal damages from the storm and all items & amenities have been r ...
From $163 per night (USD)VRBO
- From $120 per night (USD)
Expedia
Pine Island Breeze where you can relax, swim, fish, see dolphins and manatees!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island Breeze, an island experience without leaving the country. Great place to relax, swim, fish, bike ride, explo ...
From $120 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Charming 2\/2 Incredible Water Views with Boat Lift!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This immaculate 2 bedroom 2 bathroom home is canal front with Direct Access to the Intra-coastal Waterway, your gateway ...
From $226 per night (USD)VRBO
- From $149 per night (USD)
Expedia
Old world Florida luxury waterfront sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This luxury unit on the open waters of the Matlacha Aquatic Preserve is part of a double unit and is now ready for guest ...
From $149 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Beautiful waterfront home with heated pool, dock, bikes, and kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and thank you for looking into Casa High Tide!! New owners have recently made lots of upgrades to this wonderful ...
From $225 per night (USD)VRBO
- From $160 per night (USD)
Expedia
6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep six gu ...
From $160 per night (USD)Expedia
- From $130 per night (USD)
VRBO
4 Person 1 Bedroom Condo with Waterview Patio - Snapper - Welcome to our newly renovated one-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $130 per night (USD)VRBO
- From $110 per night (USD)
Expedia
2 Person Efficiency with Waterview Patio - Anchor's Inn - Welcome to our newly renovated efficiency, where comfort meets style.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated one-room efficiency, situated on the beautiful Gulf coast. Relax in the comfort of our qu ...
From $110 per night (USD)Expedia
- From $260 per night (USD)
VRBO
8 Person 3-Bedroom Condo with Private Patio - Mermaid - Welcome to our newly renovated, luxurious and spacious three-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated three-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep eigh ...
From $260 per night (USD)VRBO
- From $210 per night (USD)
Expedia
8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated two-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep eight ...
From $210 per night (USD)Expedia
- From $627 per night (USD)
VRBO
Newly Remodeled 4 Bedroom House w Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nama-Stay is located on a barrier island in southwest Florida. In fact, the only way to get to the island by boat or pri ...
From $627 per night (USD)VRBO
- From $164 per night (USD)
Expedia
Waterfront House near Boca Grande Pass!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Authentic fishing cottage! Waterfront house with access to world class fishing. Come via boat, trailer your boat, or cha ...
From $164 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Minutes to the beach w\/private pool, elevator, ocean view!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Turtle Cove! This gorgeous home will provide multiple families with a well stocked kitchen, comfortable beds ...
From $600 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Boat Dock & Island Clubs Included 3 pools, Kayaks, Tennis & 5 min walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on North Captiva Island, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pool ...
From $302 per night (USD)Expedia
- From $343 per night (USD)
VRBO
A True JEWEL on the Water - includes Boat and Spa!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Jewel of the Water - this spacious home boasts 4 bedrooms, 2 of which have ensuite baths. Dock and lift with 24ft Sweet ...
From $343 per night (USD)VRBO
- From $699 per night (USD)
Expedia
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SANTA CLARA BEACH HOUSE is a NEW LISTING and is a luxurious, newly furnished 3 bedroom harbor front rental property loca ...
From $699 per night (USD)Expedia
- From $716 per night (USD)
VRBO
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Introducing Beach Paradise: A Luxurious Beachfront Retreat on North Captiva Island, Now Available for your next vacation ...
From $716 per night (USD)VRBO
- From $150 per night (USD)
VRBO
New Home in the heart of Pine Island. Private & Pet Friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to the island! Where the pace slows to a crawl and umbrella drinks await youEasy walk to swimming, tennis and s ...
From $150 per night (USD)VRBO
- From $689 per night (USD)
VRBO
NORTH CAPTIVA PEARL - Newly Completed multi level - Two Golf Carts - Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly completed, professionally designed multi-level, multi-deck home is located just 300 feet from the widest beac ...
From $689 per night (USD)VRBO
- From $142 per night (USD)
Expedia
Casa Florida 🌴 waterfront home with boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
☞ Wifi ☞ Free boat ramp ☞ Walk Score 70 (Walk to cafes, dining, shopping etc.) ☞ 50” Smart TV ☞ Private patio w/ seatin ...
From $142 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Looking for a 3 month renter. Book at this great rate!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our condo is available for the 2024 season. This 2 bedroom, 2.5 bathroom is located at the north end of Pine Island. Th ...
From $150 per night (USD)VRBO
- Click For Pricing
Expedia
Matlacha Home w\/ Boat Mooring & Gulf Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make your next Florida vacation one to remember when you book this 2-bedroom, 1-bathroom vacation rental in Matlacha! Fe ...
Click For PricingExpedia
- From $142 per night (USD)
VRBO
2\/2 Home in Bokeelia, Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pi ...
From $142 per night (USD)VRBO
- From $229 per night (USD)
Expedia
4\/2 Pool Home with Downstairs Unit included, BOAT LIFT!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mermaid Haven! This property is undeniably a vacation renters dream home. As you walk through the front door, ...
From $229 per night (USD)Expedia
- From $268 per night (USD)
VRBO
3\/2 Beautiful Pool Home on the Water!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
There is nothing better than slipping away to your tropical paradise vacation home knowing that everything is in tip top ...
From $268 per night (USD)VRBO
- From $683 per night (USD)
Expedia
🐠Waterfront Island and Pool Dream Retreat!🐋
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
🌴Unique and tranquil getaway. No hurricane damage 🐠Heated pool on the water… make your families dream vacation! 🏖Priv ...
From $683 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Boaters Paradise in beautiful St. James City
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bring your own boat or rent one while you stay and play. Close to the gulf with easy access by boat. Great for water re ...
From $125 per night (USD)VRBO
- Click For Pricing
Expedia
**Fishing Cottage * Gulf Access * Romantic Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Adventure awaits. Enjoy ocean access for fishing near and around the scenic Charlotte Harbor. This cottage sit ...
Click For PricingExpedia
- From $152 per night (USD)
VRBO
Dog-friendly waterfront home with heated pool, lanai, central AC, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beverly's Tarpon Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $152 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Canal-front, island paradise sleeps 9 with pools, kayaks, bikes and more!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Island Paradise! Located on the north end of Pine Island, this stunning canal-front home is light and bright ...
From $325 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Sandy Toes Villa - North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sandy Toes Villa is a three bedroom, two bathroom townhome located within the Safety Harbor Club on North Captiva Island ...
From $188 per night (USD)VRBO
- From $123 per night (USD)
Expedia
Quiet, clean & comfy 2 bed-2bath with 8000lb boat lift and large screened lanai
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute, clean and comfy 2 bed, 2 full bath mobile home in Saint James City, Florida on a quiet canal with 8000 pound boatl ...
From $123 per night (USD)Expedia
- From $110 per night (USD)
VRBO
2 Person Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $110 per night (USD)VRBO
- From $218 per night (USD)
VRBO
The Hook Oar House - Waterfront Retreat with Private Boat Lifts - 2B\/2B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to The Hook Oar House, your perfect waterfront retreat for fishing, kayaking, and boating in St. James City, Flor ...
From $218 per night (USD)VRBO
- From $113 per night (USD)
VRBO
Waterfront Effeciency Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy efficiency apartment attached to the "Hook Oar House" has everything you need for a comfortable and relaxing ...
From $113 per night (USD)VRBO
- From $125 per night (USD)
Expedia
GORGEOUS RENTAL! Paradise In Old Time Florida at \"The Dew Drop Ian\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very secluded on a dead end road. Fabulous Stilt Cottage where the breeze keeps you cool all day in the many open air si ...
From $125 per night (USD)Expedia
- From $335 per night (USD)
VRBO
SIMPLY GORGEOUS BEACH HOME 360 VIEWS, 2 CARTS, 2 MINS 2 BEACH+CLUB POOLS, KAYAKS
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
RARE OPENING JUNE 10TH THRU JUNE 15TH - 5 NIGHT SUMMER OPENING AND GREAT RATE PLEASE INQUIRE! COASTAL SOUL is Being Of ...
From $335 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Pine Island Breeze\/Bokeelia 1 Bdrm 1 bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A perfect place to be as close to people or as far away as you like. Pine Island is 20 minutes to busier areas of Fort ...
From $150 per night (USD)VRBO
- From $158 per night (USD)
VRBO
Amazing sunsets, Fishing from the dock, Large lanai & Pool - Villa Boa Vista - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Boa Vista "Villa Boa Vista" is the perfect vacation spot for your next getaway. This gulf access canal home with ...
From $158 per night (USD)VRBO
- From $764 per night (USD)
Expedia
Spectacular Sunsets. Private multilevel designer home with heated pool and spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Multilevel Designer Home with plenty of room for family. Multiple living areas and plenty of outside areas to enjoy. T ...
From $764 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Beautiful pool home on canal with 45-foot boat dock. 10 minutes to Gulf by boat.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island is the No. 1 Tarpon fishing spot in the world. Many islands to go to for shelling, fishing, dining. After yo ...
From $250 per night (USD)VRBO
- From $111 per night (USD)
VRBO
Are you looking for old Florida.? Lower heart rate? No high rises\/ traffic?
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Florida style home is for guests who want to relax and unwind. It is located on a quiet street and the refreshing ...
From $111 per night (USD)VRBO
- From $785 per night (USD)
VRBO
Family friendly home with heated pool - only 300 feet from the beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Well appointed, well maintained home on beautiful North Captiva Island. Private heated pool, hot tub and two screened p ...
From $785 per night (USD)VRBO
- From $624 per night (USD)
VRBO
NEW LUXURY BEACHFRNT, SPECATULAR OCEAN VIEWS, BEST BEACH W\/PRIVATE ACCESS + CLUB
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
BRAND NEW, FULLY REMODELED TOWNHOUSE WITH TWO MAIN SUITES LOCATED DIRECTLY ON THE BEST NORTH CAPTIVA ISLAND BEACH AND WE ...
From $624 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Bokeelia Charming Island House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your getaway home- a newly remodeled spacious 3 beds 2 bath house, the left side unit of a duplex. Quiet and ...
From $120 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Summer Deals! New 4\/4 Beach House with Pool, Spa, Game Room -1 Min from Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax and enjoy this unique piece of island paradise from our spacious, custom designed, luxury home just one minute wal ...
From $450 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Beautiful Matlacha Isles direct access waterfront home with dock, lift and deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy your stay in this large 3 Bedroom 2 1/2 Bath direct access waterfront home. Dock your boat on the covered lift and ...
From $214 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Oceanfront Luxury Home with Secluded Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Sandcastle is a completely updated beachfront home that has been owned by a single family for over 40 years, and i ...
From $650 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Bokeelia, Pine Island House w\/ kayaks, canoes, & Bikes, on canal w\/ private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bokeelia Tropical Getaway is the perfect escape on the north tip of Pine Island for kayaking, canoeing & bike riding (in ...
From $189 per night (USD)VRBO
- Click For Pricing
Expedia
AVAILABLE FOR EASTER! 🛏️ 4 Bedrooms 🛁 4.5 Bath Pool Home on Pine Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy the island life at this tastefully decorated Ranch style pool home in Bokeelia. This property is conveniently ...
Click For PricingExpedia
- From $110 per night (USD)
VRBO
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $110 per night (USD)VRBO
- From $140 per night (USD)
Expedia
4 Person 1 Bedroom Condo with Waterview Balcony Fisherman Cabin - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $140 per night (USD)Expedia
- From $767 per night (USD)
VRBO
438 - Reel Laxing North Captiva
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Wasson Family (Lisa, Cory & Colby) would like to Welcome you to North Captiva Island and “Reel Laxing”, the house wh ...
From $767 per night (USD)VRBO
- From $160 per night (USD)
VRBO
Beautiful Florida house near the marina on Pine Island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Come stay in our beautiful Florida home! The house is fully stocked with a lot of character. It boasts hardwood floors, ...
From $160 per night (USD)VRBO
- From $432 per night (USD)
VRBO
AWESOME NEW POOL HOME SPRAWLING OUTDR ENTERTAINING AREAS\/STEPS2OCEAN\/2CARTS\/DOCK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
BRAND NEW HOME AND RENTAL! NOW BOOKING FOR VACATION RENTALS! TYPICALY 7 NIGHT RENTALS - WEEKENDS TO WEEKENDS during Pr ...
From $432 per night (USD)VRBO
- From $89 per night (USD)
Expedia
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $89 per night (USD)Expedia
- From $84 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $84 per night (USD)VRBO
- From $77 per night (USD)
Expedia
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
You will enjoy great holiday days right here in one of the best places on earth! We guarantee the most beautiful sunset ...
From $77 per night (USD)Expedia
- From $89 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $89 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Pet-Friendly \/ Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
ANGLER'S INN in Matlacha, Florida is a pet-friendly waterfront "Botel" accommodation located between Cape Coral and Pine ...
From $165 per night (USD)Expedia
- From $154 per night (USD)
VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Hook Studio". Compared ...
From $154 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Studio on the Water. Great for monthly stays!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Rod Studio". We are loc ...
From $153 per night (USD)VRBO
- From $81 per night (USD)
VRBO
REOPENED SINCE NOVEMBER 2023!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Apartment "Snook Suite" with 4 beds - open living / sleeping area - well equipped kitchen and dining area for 4 persons ...
From $81 per night (USD)VRBO
- From $81 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Studio "Redfish Room" in a house with 4 apartments, open water - cozy atmosphere in an open living-sleeping area with fu ...
From $81 per night (USD)VRBO
- From $75 per night (USD)
VRBO
BEST FISHING AREA \/ Fishing Kayaks available
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Studio "Grouper Room" - comfort in the smallest space - living, sleeping, cooking - ideal for singles and couples - well ...
From $75 per night (USD)VRBO
- From $75 per night (USD)
VRBO
Reopened in November 2023!!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $75 per night (USD)VRBO