Calusa Land Trust and Nature Preserve of Pine Island, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Calusa Land Trust and Nature Preserve of Pine Island, Florida on RentalSaver.com!

Calusa Land Trust and Nature Preserve of Pine Island Rentals

From $337 per night (USD)
VRBO
Beautiful house / charming Island / great fishing, manatees, dolphins. NO LANAI
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Grandpa Rudy first came to Pine Island in 1954 and our family has been coming ever since! Grab a cup of coffee (tea or ...
From $337 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Gorgeous & Spacious 3/3.5, Incredible Water Views! Sleeps 9!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Incredible 3 bedroom 3.5 bath home with endless water views! This brand new renovated home offers so much space for the ...
From $389 per night (USD)
Expedia
From $1566 per night (USD)
VRBO
Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 🌊 Gulf Front Paradise 🏊‍♂️ Heated Private Saltwater Pool 🌅 Hot Tub Bliss: Enjoy stunning sunsets from the s ...
From $1566 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Margaritaville! 3bd2ba house in Saint James City 2 mins to open water w13k lift.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this charming house in picturesque Saint James City. Close to everything on a quiet and quaint culdesac. With ...
From $326 per night (USD)
Expedia
From $256 per night (USD)
VRBO
WATERFRONT, POOL, BOAT LIFT, WALKING DISTANCE TO RESTAURANTS, 2 BED/2 BATH
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the beauty of Matlacha from this lovely 2-bedroom house. With a king bed and a Day bed that converts to a king ...
From $256 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Silverseas Cottage-Luxury 3-bedroom, Steps to the Beach, Pool, 2 Carts, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
SILVERSEAS COTTAGE, The Perfect Beach Vacation Mere Steps From the Beach! Experience the ultimate beach vacation! Our ex ...
From $734 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Luxurious waterfront home, pool, boat dock, fillet station, private guest suite
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Coastal Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $543 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Spacious, dog friendly home with pool, on waterway within minutes to the Gulf
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bowline Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $446 per night (USD)
Expedia
From $641 per night (USD)
VRBO
North Captiva House on the Runway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to "One Margarita" on North Captiva Island! This charming 3-bedroom, 3-bath beach house is perfect for families ...
From $641 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Florida Style Villa by the Water with heated Pool, Dock, Gulf access! Kayaks!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You love the water... then this is your place to be! The villa has been completly renovated in 2024! Start kayaking or b ...
From $299 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Treetop getaway on a secluded Island with gulf coast beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to paradise! Your North Captiva Island stay includes The Island Club access to clubhouse pools, pool bar, hot t ...
From $658 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Cabana @ 2 Fish Inn Pool Side
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Are you searching for your slice of island paradise while on vacation? Look no further than the Cabana at the 2 Fish Inn ...
From $203 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Dream Vacation Pool and Waterfront Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
With its prime waterfront location, luxurious pool, and beautifully appointed living spaces, this 2-bedroom, 2-bathroom ...
From $279 per night (USD)
VRBO
From $132 per night (USD)
VRBO
Gulf Access Lake View Bokeelia Condo with Boat Slip.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Walking, biking, boating, local dining and friendly people on Pine Island! This 2-bedroom condo is perfect for your esca ...
From $132 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Boater’s Paradise! Beautiful Home on the Water with 2 Boat Lifts & Dockage Space
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Beautiful Newly Remodeled Home located right On the Water in Florida’s Best Kept Secret… Bokeelia In Pine Island, FL. Th ...
From $297 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Luxury Island Escape @ Palm Tree Villa: Private Rooftop Deck & Saltwater Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Palm Tree Villa, a luxurious retreat nestled on Pine Island’s serene Gulf Coast in Southwest Florida. Spannin ...
From $476 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Beautiful Island Sanctuary with Modern Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our upscale, spacious 3 br/2 ba home, located in a quiet neighborhood Bokeelia. Here, you and your family can ...
From $282 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Do you like to fish, relax, chill and enjoy nature? Do we have the place for you
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sonny Palms. This Direct Gulf Access Home has been completely remodeled in fall of 2021. This home offers: 3 ...
From $384 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Boaters Paradise in Matlacha Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This peaceful yet centrally located cottage within walking distance to town has an open floor plan with master suite and ...
From $285 per night (USD)
VRBO
From $258 per night (USD)
Expedia
NEW!! The “WATERSIDE” COTTAGE~With dockage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
World class tarpon fishing, superb flats fishing for reds, & Snook in the mangroves, Trout in the grass, giant Sharks in ...
From $258 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Pine Island Beach House! *Gulf Access, Heated Pool, Hot Tub & Boat Dock*
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the "Blue Marlin"! St. James City on Pine Island is a fishing and boating community with old Florida charm! ...
From $382 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Beautiful waterfront 2-bed/2-bath island getaway on Matlacha Island.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Coqui Palace is a waterfront two bedroom, two bath island getaway in the Historic Matlacha Fishing Village. Fish fro ...
From $275 per night (USD)
Expedia
From $309 per night (USD)
VRBO
First-floor, snowbird-friendly townhouse w/ shared pool, WiFi, central AC, & W/D
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Mermaid Haven at Bocilla Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $309 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Blue Pearl-close to beach, screened porch, club, courtesy golf cart for 4.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This cute open concept home is great for gathering, relaxing, and making memories. Stroll just a few minutes to the whit ...
From $373 per night (USD)
Expedia
From $999 per night (USD)
VRBO
4 Bedroom Beach Home on a Private Island with a Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy spectacular views of Captiva Pass and Pine Island Sound from this professionally decorated Tropical Island Beach h ...
From $999 per night (USD)
VRBO
From $293 per night (USD)
Expedia
SEASIDE VILLA MANATEE BAY in quiet location on Pine Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy the Island Life in our sun filled vacation home located off Manatee Bay, just north of Saint James City on Pine Is ...
From $293 per night (USD)
Expedia
From $756 per night (USD)
VRBO
Steps from the beach! Spacious island retreat with pool, grill, and space for 12
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Coquina Beach House, your home-away-from-home on private North Captiva Island! Just a 4-minute walk from the ...
From $756 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Beautiful waterfront Key West style home with a pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Private, spacious Key West style home located on a canal with quick access to the pine Island sound. 3 bedroom 3 full ...
From $344 per night (USD)
Expedia
Click For Pricing
VRBO
Breathtaking Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
It’s an authentic Florida paradise! This special place is close to everything, making it easy to plan your visit whethe ...
Click For Pricing
VRBO
From $1081 per night (USD)
Expedia
Manatee Haven: Screened-in Pool, Spa and Elevator! 2 Golf Carts
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Manatee Haven has been fully rebuilt and renovated post Hurricane Ian. The house is spectacular. Manatee Have ...
From $1081 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Bokeelia Retreat - Fishing Docks & Canals Nearby!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Prepare for rest and relaxation when you book a stay at this 3-bedroom, 2-bathroom vacation rental home in Bokeelia! Loc ...
From $240 per night (USD)
VRBO
Click For Pricing
Expedia
Very private, 3 decks, a pond with many birds. Island living, access to mainland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very private on one acre of land with no neighbors, wild peacocks, ibis, herrons, Eagles woodpeckers, cardinals, ducks, ...
Click For Pricing
Expedia
From $273 per night (USD)
VRBO
Peaceful retreat. Fishing Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax with the whole family at this peaceful place to stay. Located in 1.04 acre of land this 3 bedrooms and two bathro ...
From $273 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Paradise Found: 3/2 Home with Pool, Canal Access, and Pet-Friendly Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the comfort and convenience of our exceptional ground level vacation rental home. Nestled on the Monroe Canal ...
From $296 per night (USD)
Expedia
From $369 per night (USD)
VRBO
3 Master Suites-EVERYTHING is new pool home on the water
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to our amazing waterfront vacation home, where luxury and comfort await you. This newly renovated retreat featur ...
From $369 per night (USD)
VRBO
From $196 per night (USD)
Expedia
2 bed/ 2.5 bath Waterfront Condo with 2 pools and great fishing
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the ultimate comfort and relaxation at this beautifully remodeled garden front condo. With its inviting ambia ...
From $196 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Condo w use of a 10k boat lift. 5min to open water. Tarpon capital 15min away
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Marina Gardens located on a peninsula surounded by Jug Creek in Bokeelia at the north-end of Pine Island on Florida's we ...
From $251 per night (USD)
VRBO
From $311 per night (USD)
Expedia
SANDY TUNDRA TOWNHOUSE, WATER-VIEWS, BOAT SLIP, PRIVATE BEACH, CLUB ACCESS
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
SANDY TUNDRA is a luxurious 3 bedroom waterfront townhouse with Safety Harbor Club access and the use of a private boat ...
From $311 per night (USD)
Expedia
From $446 per night (USD)
VRBO
The Salty Snook - LARGE BEACH HOME w/VIEWS!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
SPECIAL OPENING PRIME 4TH OF JULY WEEK AVAILABLE! JUNE 28TH or earlier to JUNE 5! Please inquire! - 7 night+ rental! ...
From $446 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Beautiful Waterfront Ideal for fishing and boating!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a fisherman;s paradise with a boat lift, and you are only minutes from the waters of Pine Island Sound. This ar ...
From $277 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Romantic beach home with golf cart Remodeled Coastal charm
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Amazing property , newly renovated vacation home with 1800 square feet for you to enjoy , all air conditioned . Enjoy i ...
From $313 per night (USD)
VRBO
From $272 per night (USD)
Expedia
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Find your ideal vacation home that fisherman and their wives love to bring their familys and vacation in Matlacha.Plenty ...
From $272 per night (USD)
Expedia
From $773 per night (USD)
VRBO
Private beach oasis -- 2-minute walk to the ocean! w/ Golf Cart & Club Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The first thing you See or should we say "Sea" is the breathtaking Gulf of America from virtually everywhere from each ...
From $773 per night (USD)
VRBO
From $842 per night (USD)
Expedia
Tipsy Turtle: Views from 4 Decks, Swim-up Pool Bar
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Are you familiar with what it takes to vacation on North Captiva Island, FL? (If you are, you're welcome to jump down to ...
From $842 per night (USD)
Expedia
From $252 per night (USD)
VRBO
The Quarterdeck Cottage~Boat dockage available directly across the street
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With dockage (across the street at my privately owned property) and golf carts available for your stay (additional fee)B ...
From $252 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come, enjoy this 3 bedroom/2 bath 2000 sq.ft. home in Saint James City with over 150 feet of seawall. This Villa is a fi ...
From $301 per night (USD)
Expedia
From $701 per night (USD)
VRBO
The Wheelhouzz - Luxury Island Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Wheelhouzz is a beautiful three-bedroom beach property in Safety Harbor Club on North Captiva Island. It is privatel ...
From $701 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Cozy, clean duplex with outdoor dinning.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Have your vacation in Paradise! This duplex is located in the heart of Pine Island a couple of blocks of the four way st ...
From $149 per night (USD)
Expedia
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VRBO
Yellow Fin Cabin of Matlacha
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Famous Matlacha island with tourism and fishing. Many restaurants and bars at walking distance. The best fishing off a b ...
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VRBO
From $225 per night (USD)
Expedia
Well Equipped Pet/Smoke Free Family Home - bring your boat!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WE DON'T LIVE IN A SQUARE WORLD, WHY VACATION IN A SQUARE HOUSE? Come and experience the unique feel of a round house de ...
From $225 per night (USD)
Expedia
$Windows on the Water \W.O.W\ An ocean front oasis!$
From $737 per night (USD)
VRBO
Windows on the Water \"W.O.W\" An ocean front oasis!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
House, 3 bedrooms - 3 full bath. Our renovated home is named "Windows on the Water" because of the spectacular wall of ...
From $737 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Piece of Paradise for All Seasons!!! Bring Your Boat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Castaway Cottage is waiting for you! Come enjoy fishing and boating, or just relax with a cocktail in the screened lanai ...
From $255 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Kaya Del Sol, the perfect family trip!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to a magical island paradise! This quintessential family or couples' retreat inspires a relaxed peaceful ambience ...
From $681 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Island Paradise: Steps to Private Gulf Beaches, Pools, Hot Tub & Golf Cart ALL
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
North Captiva Retreat A Whisper Away from Pristine Gulf Shores Elevate your Florida vacation by choosing our 2-bedroom, ...
From $458 per night (USD)
Expedia
From $1426 per night (USD)
VRBO
Gulf of America Beach House, Private Pool, 360 Island Views Airstrip Membership
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Perfect Landing on North Captiva Island. 4 bedroom 3 bath.. 3 King suites plus bunkroom. Owner has Airstrip membership a ...
From $1426 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Modern Villa SW of Cape Coral in quiet Surfside Blvd area with gulf access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Privacy, silence and relaxation are guaranteed at Villa Eyleen, located at one of the widest canals in Cape Coral. The r ...
From $293 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Direct Gulf Access Island Retreat - Boat Lift, No Bridges, Convenient Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing, spacious stilt home offers 2 bedrooms and 2 bathrooms, Direct Gulf Access, Covered Boat Lift, gorgeous vie ...
From $242 per night (USD)
VRBO
From $830 per night (USD)
Expedia
Private & Spacious [2300sqft] home w/Pool,Hot Tub,Golf Cart, Pet Friendly & Club
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Complete exterior renovation completed March 2023 Welcome to our home on North Captiva Island. Remote and undiscovered, ...
From $830 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Welcome to Seabatical a barrier island get-away accessible only by boat or ferry
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy North Captiva Island! Seabatical, 3BR/2BA townhouse with great views waiting for you to enjoy sitting on the scree ...
From $450 per night (USD)
VRBO
From $213 per night (USD)
Expedia
NEWLY REMODELED-Peaceful Florida Island Home-5 minute canal ride to Gulf waters!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Come relax in our Pine Island dream home--a charming, open and colorful floor plan will remind you that you are on a Flo ...
From $213 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Island Home within the Pines and Palms; Kayaks, Bikes, and Inviting Porches~
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Unique custom-built Key West style piling home with outdoor shower, plentiful parking underneath as well as long drivewa ...
From $180 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Hidden Treasure - near Beach-Pool- Club Use - Dock available - 10% off weekly !!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
X marks the spot! Choose Hidden Treasure for your ultimate Island Getaway. Tucked away on at the end of a quiet cul-de- ...
From $646 per night (USD)
Expedia
From $909 per night (USD)
VRBO
SERENITY NOW~1 Min. To BEACH!-SCREENED-IN HEATED POOL-2 Carts-4&6, Island Club
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
SERENITY NOW has Gulf Sunrises and expanded Harbour views! luxurious 6~ bedrooms (4 Kings) 5~ full bathroom, 2 Golf Cart ...
From $909 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Gorgeous, Peaceful Island Retreat-3 Bedroom-2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
It’s time for a Cool Change! Brand new rental available on Upper Captiva Island! Cool Change is a recently renovated, br ...
From $413 per night (USD)
Expedia
From $191 per night (USD)
VRBO
TURTLE COTTAGE AN ISLAND OASIS - PINE ISLAND
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
"ISLAND VIBE" "Pine Island" Turtle Cottage is a totally remodeled, fully furnished and well appointed home located in th ...
From $191 per night (USD)
VRBO
From $242 per night (USD)
Expedia
🔆🏝LITTLE PARADISE🏝🔆
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the ...
From $242 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Just Listed - Beautifully renovated waterfront 2 bedroom home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic 2 - bdrm 3 - bed waterfront (w doc) home ready for guests now. Perfect location on the north tip of Pine Isla ...
From $527 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
Flamingo Beach: Beachfront Home with Endless Relaxation & Gulf Views
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Flamingo Beach House, your ultimate beachfront retreat on North Captiva Island. This luxurious 5-bedroom home ...
From $1181 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Paradise Found with Pool & 2 Boat lifts
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This gorgeous 3/2 offers a wonderful gulf access, split plan dressed in island style complete with pool, 2 boat lifts an ...
From $293 per night (USD)
VRBO
From $1027 per night (USD)
Expedia
The MAINE DECK - BRAND NEW DESIGNER HOME WITH PRIVATE POOL AND 2 GOLF CARTS
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
BRAND NEW HOME - SCHEDULED FOR COMPLETION 02/28/2022 Welcome to the Maine Deck! Our beautiful dream home is brand new w ...
From $1027 per night (USD)
Expedia
From $101 per night (USD)
VRBO
Best Deal Available for a monthly rental home during season! 🏝️🐬
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
If you're looking to get out of the cold weather this winter, this is the perfect place to relax, fish, walk to the Blue ...
From $101 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Perhaps you have spent vacations in a large busy city that is full of famously produced theatre presentations and name b ...
From $149 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Tropical Island Resort Nestled on the Gulf Coast of Southwest Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bocillia Island Club located in Bokeelia on the north-end of Pine Island on Florida’s west coast and the last of Old Flo ...
From $239 per night (USD)
VRBO
From $490 per night (USD)
Expedia
CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning waterfront property in gorgeous Safety Harbor Club. Enjoy breathtaking views and the best the island has to off ...
From $490 per night (USD)
Expedia
From $342 per night (USD)
VRBO
2/2 Pool Home on the Water, Boat Lift Included!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Waterfront Paradise in St. James City | Heated Pool, Dock, Gulf Access 2 Bed | 2 Bath | Sleeps 4 | Boat Lift | Bikes | ...
From $342 per night (USD)
VRBO
From $1048 per night (USD)
Expedia
Tropical Family Oasis: Pool, Spa, Golf Cart – End of Year Deals & Specials!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Green Tortuga: Your Tropical Oasis Awaits! Escape to Green Tortuga and experience the ultimate Caribbean get ...
From $1048 per night (USD)
Expedia
From $250 per night (USD)
VRBO
St. James City Vacation Home with Private Dock, Pool and Gulf Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Rum N Reel • St. James City Vacation Rental Escape to island paradise at Rum N Reel, your ultimate waterfront vacation ...
From $250 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Immerse yourself in the idyllic charm of this three-story Key West style residence, perfectly situated to offer unsurpas ...
From $575 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Private dock with 2 golf carts Oceanfront home Absolute Best Location on island!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
All brand new. Complete remodel. Be the 1st guest in. Located overlooking Safety Harbor. 2 Amazing decks overlooking the ...
From $769 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Private Pool & Deck: Canalfront St James City Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Endless aquatic activities await at this St. James City vacation rental! This 3-bedroom, 2-bathroom home offers a Gulf C ...
From $279 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Bokeelia Cottage w/ Private Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Find a tropical paradise in your own backyard at this 2-bedroom, 2-bathroom Bokeelia vacation rental cottage! With all o ...
From $206 per night (USD)
VRBO
From $562 per night (USD)
Expedia
Coconut Castaway-Ocean Views, Golf Cart, Club Pool, Walk to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
**Once booked, you will need to complete and sign a vacation rental agreement** *Please note: We recognize, based on fee ...
From $562 per night (USD)
Expedia
From $1197 per night (USD)
VRBO
SPRAWLING PRIVATE BEACHFRONT - Sleeps 10, perfect for a family, 2 golf carts
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to SEA LA VIE beach house, your luxurious home away from home at the shore. Our private 4 bedroom beach house of ...
From $1197 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bring the boat, kayaks, bikes and water toys. This high and dry Pine Island home on a canal has withstood all the storms ...
From $263 per night (USD)
Expedia
From $926 per night (USD)
VRBO
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
*This property is located on North Captiva which is only accessible by ferry or boat. * Our home, Dreamcatcher, is on N ...
From $926 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Island TreeTop House, Pet friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Lovely cozy 2bed 1bath secluded house in quiet neighborhood. My home is very clean and uncluttered. Great for Two or t ...
From $158 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Waterfront cottage in Matlacha, FL -<br>Unavailable at this time due to Hurr Ian.🌴
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our paradise cottage is in the cutest, artsiest, fishingest town, Matlacha FL, on Pine Island. Clean, updated and beauti ...
From $294 per night (USD)
VRBO
From $453 per night (USD)
Expedia
North Captiva Island- Ocean bay views and modern decor. Two new carts!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Bay - North Captiva Island Welcome to paradise! This townhome boasts the best of ocean bay views, wild beaches w ...
From $453 per night (USD)
Expedia
From $344 per night (USD)
VRBO
The Perfect Day in Matlacha! Direct Gulf Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kick back & relax enjoying all that South West Florida has to offer!! Savor your morning coffee or evening wine on a bea ...
From $344 per night (USD)
VRBO
From $729 per night (USD)
VRBO
THE BIRDS & THE BEACH - 4 bed 3 bath, Sleeps 12, HUGE Private Pool, 2 GOLF CARTS
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
SPACIOUS 4 BR. 3 BATH - sleeps 12 in beds, 2 Golf Carts, PRIVATE HEATED POOL , Most of the house is completely new, ...
From $729 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Sunset Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Matlacha, it’s a water sports paradise! World class fishing, boating, kayaking, beautiful sunrises and sunsets! See natu ...
From $482 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Fun'n Sun-Charming 3 BR/3 baths waterfront villa- pool, spa, dock, fishing poles
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is a boater’s and fisherman’s delight. Fully stocked, and beautifully furnished 3-bedroom 3-bathroom water ...
From $324 per night (USD)
Expedia
From $772 per night (USD)
VRBO
Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Captiva Beach Sunset 5 BR / 4.5 BA | Sleeps 15 in beds (plus 2 twin recliners, perfect for kids!) | Beachfront | Private ...
From $772 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Come enjoy a beautiful gulf access condo in Bocilla Island Club, at the northern tip of Pine Island. Enjoy your morning ...
From $220 per night (USD)
Expedia
From $625 per night (USD)
VRBO
LUNAR TIDES - 3 BR/2 BA - Your dream vacation spot! Private Pool - 1 Golf Cart
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your dream vacation to an island paradise is just a few clicks away! Lunar Tides is located on the barrier island of No ...
From $625 per night (USD)
VRBO
From $736 per night (USD)
Expedia
SANDPIPER INN - TRUE BEACHFRONT Luxury; Pool/Hot tub & Golf cart NEW LISTING
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
SANDPIPER INN – BEACHFRONT CONDO – POOL – GOLF CART Experience the ultimate beachfront getaway at this stunning beachfro ...
From $736 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Waterfront Bungalow in Matlacha
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the perfect getaway at this charming one-bedroom, one-bathroom waterfront bungalow. Nestled along the serene sh ...
From $223 per night (USD)
VRBO
From $397 per night (USD)
Expedia
3634 Bayview Avenue (Paradise): 3 BR, 2.5 BA House in Saint James City, Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your dream vacation destination, located in the highly sought-after waterfront community of Bayview Acres in ...
From $397 per night (USD)
Expedia
From $162 per night (USD)
VRBO
St James City brand new 3-bedroom home with WiFi, AC and boat lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Unwind in Saint James City at this adorable mobile home. With 3 cozy bedrooms including 2 queen beds and 1 twin bed, gue ...
From $162 per night (USD)
VRBO
From $950 per night (USD)
Expedia
Villas in the Air – Elevated Island Living!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 🏊‍♂️ Heated pool on the main level—no stairs for easy access! 🛋️ Thoughtfully designed with elevated interio ...
From $950 per night (USD)
Expedia

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