Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $3000 per night (USD)VRBO
Beachfront🌊4 KING suites&bunk room🛏️Pet Friendly🐾
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 12
🛥️New offering: Free boat dock 👙GULF FRONT 180° amazing beach views 🏠Professionally designed/decorated 🛌🏽Westin Hea ...
From $3000 per night (USD)VRBO
From $148 per night (USD)Expedia
Island Paradise, waterfront location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Quiet island living, with quick access to pine island sound from your dock. Great kyaking, fishing and 16 miles of safe ...
From $148 per night (USD)Expedia
From $825 per night (USD)VRBO
The Salty Conch - Luxury Just Steps To The Beach with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Book your stay at the beautiful, new to the rental market, island house, just a short golf cart ride to the beach! The ...
From $825 per night (USD)VRBO
From $409 per night (USD)Expedia
Townhome with stunning view of Matlacha Pass
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning Views….A unique town home community nestled on the island of Matlacha. This Matlacha location is literally minu ...
From $409 per night (USD)Expedia
From $244 per night (USD)VRBO
Beautiful, cozy, clean & fresh house on a canal with private ramp, spce to moore
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This house is located at the North of Pine Island, a tranquil, scenic, peaceful, tropical scenery. The area is renown fo ...
From $244 per night (USD)VRBO
From $390 per night (USD)VRBO
pool house on 2 acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island stilt house,close to lavenderlanding boat ramp,jug creek and 4 winds marina,bokeelia pier, lazy flaming and capt ...
From $390 per night (USD)VRBO
From $469 per night (USD)VRBO
Direct Gulf Access w\/ 60' Boat Dock \/360 Views\/ Private Heated Pool\/Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
White Sands is a luxury custom built waterfront home completed in 2022. Heated pool and direct access to the Gulf of Mex ...
From $469 per night (USD)VRBO
From $959 per night (USD)Expedia
VILLA IN THE AIR - 2 Golf Carts, Private Pool, Steps to the beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Gorgeous 5 bedroom home with heated elevated pool. So much space at the poolside with sun-beds and screened outdoor liv ...
From $959 per night (USD)Expedia
From $808 per night (USD)VRBO
Ocean views, sleeps 10, heated pool, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
***Milton Update - We are happy to be accepting new bookings*** Featuring a private heated pool, a hot tub, ping pong, ...
From $808 per night (USD)VRBO
From $402 per night (USD)Expedia
Matlacha Isles Oasis w\/ Gulf Access & Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
An unforgettable Matlacha Isles getaway awaits at this radiant 3-bedroom, 2.5-bathroom vacation rental. The vibrant home ...
From $402 per night (USD)Expedia
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St James City Home on Canal w\/ Boat Davit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Whether you’re planning a snowbird retreat or a relaxing summer getaway, head to the canals of St James City for a stay ...
Click For PricingVRBO
From $817 per night (USD)Expedia
STUNNING BEACH HOME-Private Pool, Bar & Game Area. 2 Carts.\nALL YOU NEED IS FUN!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SAME OWNERS SAME HOME DIFFERENT NAME: A WAVE FROM IT ALL HAS CHANGED TO "ALL YOU NEED IS FUN" Are you ready for the be ...
From $817 per night (USD)Expedia
From $729 per night (USD)VRBO
Large home on private penninsula with water views on three sides
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Large four bedroom waterfront home built in 2008. Located on private peninsula at the end of private road with water on ...
From $729 per night (USD)VRBO
From $850 per night (USD)Expedia
Pirate's Captiva-Golf Cart and HOT Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise!! Golf cart included with your rental. Pirates Captiva was built in 2018, and withheld Hurricane lan ...
From $850 per night (USD)Expedia
From $170 per night (USD)VRBO
Charming 2 Bedroom Vacation Home w\/ Pool and Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming getaway is nestled perfectly along Jug Creek with pool, tennis courts and boat slip. Large enough for the ...
From $170 per night (USD)VRBO
From $362 per night (USD)Expedia
Bokellia Tarpon Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island life Begins here. Waterfront canal. Take Your boat to Cabbage Key Boca grande Caya costa. Tarpon Capital of the W ...
From $362 per night (USD)Expedia
From $258 per night (USD)VRBO
Beautiful Water Views, Tropical Sunsets, Gulf Access - Villa Island Escape - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Island Escape ~ Your Tropical Island Getaway awaits! Easy Gulf Access, Amazing Water Views, and Famous Matlacha ...
From $258 per night (USD)VRBO
From $538 per night (USD)Expedia
Spectacular beach front views with a short walk to members only beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom 2.5 bathroom custom built home has amazing sweeping and unobstructed views of the Gulf of Mexico with mag ...
From $538 per night (USD)Expedia
From $486 per night (USD)VRBO
Gorgeous Home - Captivating Cabana! Steps to pool, short golf cart ride to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Captivating Cabana - NEW rental on secluded North Captiva Island. A short ferry ride separates you from the hustle and b ...
From $486 per night (USD)VRBO
From $1448 per night (USD)Expedia
Luxury Beachfront Home, New Lighted Fishing Dock, Shelling, Sunrises, Renovated!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Discover a secluded and unspoiled paradise on North Captiva Island, reachable solely by ferry, private boat, or small pl ...
From $1448 per night (USD)Expedia
From $162 per night (USD)VRBO
No Rat Race here at the Royal Flush.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Hidden oasis, Secluded 1 bedroom apartment set amongst the Royal Palms and Mango Trees. Private entrance. Plenty of room ...
From $162 per night (USD)VRBO
From $233 per night (USD)Expedia
**New** Pine Island Paradise - Saltwater Canal 2 bed\/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for your own piece of island paradise? This beautifully decorated spacious 2 bedroom, 2 bathroom home in St. Jam ...
From $233 per night (USD)Expedia
Click For PricingVRBO
Your own little bit of paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautifule trailer 1 bedroom plus sofa bed so you have planty of room for 4 people . A few steps to canal that leads to ...
Click For PricingVRBO
From $440 per night (USD)Expedia
New! Modern 3 Bed Townhome on North Captiva Island w\/Beachfront views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahoy, land-ho! Gorgeous getaway destination ahead! Come visit La Casa Delphine: an elegant 3-bedroom waterfront haven, t ...
From $440 per night (USD)Expedia
From $669 per night (USD)VRBO
High Tide Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to High Tide Retreat on beautiful North Captiva Island. No cars, just fun and beaches. We are on a small island ...
From $669 per night (USD)VRBO
From $1016 per night (USD)Expedia
HIBISCUS HOUSE - Luxury Home - SLEEPS 8. 2 GOLF CARTS, POOL & CLUB MEMBERSHIP
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Hibiscus House is a wonderful vacation home for families, couples traveling together, or a romantic getaway. Located 60 ...
From $1016 per night (USD)Expedia
From $1896 per night (USD)VRBO
FALL DATES OPEN! BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL, 2 CARTS
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 17
VISIT OUR WEBSITE WWW.BEAUTYANDTHEBEACHNORTHCAPTIVA.COM BEAUTY AND THE BEACH is a 5 Bedroom with 3 Master Suites, Sleep ...
From $1896 per night (USD)VRBO
From $482 per night (USD)Expedia
Secluded Island Beach Home - Starcut Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Starcut Cottage, our dream home on our favorite island. When we stayed in this home in the spring of 2022 we ...
From $482 per night (USD)Expedia
From $427 per night (USD)VRBO
New Listing - Beach House located steps to the beach with private pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
New Listing – Beachin' & Winin', a Beach House with Private Pool Welcome to our piece of paradise!! Centrally situated ...
From $427 per night (USD)VRBO
From $206 per night (USD)Expedia
Pine Island Pearl, private home on spacious lot
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Vacation home minutes from several marinas, Matlacha restaurants and shops, hiking, golf, community swimming pool and bi ...
From $206 per night (USD)Expedia
From $224 per night (USD)VRBO
Deluxe King Suite w\/Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Deluxe King Suite is the epitome of comfort and sophistication, offering a private escape with distinct features. En ...
From $224 per night (USD)VRBO
From $223 per night (USD)Expedia
Historic Florida \"Cracker Cottage\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
NO DAMAGE FROM HURRICANE IAN!!!!! Beautiful historic property located in quaint Bokeelia, Florida. Close to boat ramps, ...
From $223 per night (USD)Expedia
From $778 per night (USD)VRBO
Waterfront home with private pool, dock, patio, balconies, & bikes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Maison de Sirens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $778 per night (USD)VRBO
From $470 per night (USD)Expedia
VRCC Villa Paradisio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
website: www.vr-capecoral.com Villa Paradisio - Located less than 500 yards from the Stonis Park, Restaurants, Tennis C ...
From $470 per night (USD)Expedia
From $418 per night (USD)VRBO
3\/3 in St James City close to restaurants, boat ramp\/marina,2 paddle-boards
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your gulf access waterfront paradise awaits! Modern home with beautiful canal views. Kick back on the dock and relax wat ...
From $418 per night (USD)VRBO
From $137 per night (USD)VRBO
Newly opened in November 2023 - direct access to the water \/ private boat deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy a great time right here in one of the best places on earth! We guarantee the most beautiful sunset of Fl ...
From $137 per night (USD)VRBO
From $138 per night (USD)VRBO
Newly opened in November 2023 - direct access to the water \/ private boat deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy a great time right here in one of the best places on earth! We guarantee the most beautiful sunset of Fl ...
From $138 per night (USD)VRBO
From $141 per night (USD)VRBO
Florida Pine Island Paradise Get-Away in Bokeelia
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your dream vacation destination! Escape to this cozy rental property nestled in sunny Florida. Whether you're ...
From $141 per night (USD)VRBO
From $137 per night (USD)VRBO
*** Newly lovely refurbished studio Snapper Room *** open for vocationers ***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
<p>Located on the waterfront, this welcoming vacation home lets you experience it all in Matlacha. Lovegrove Gallery & G ...
From $137 per night (USD)VRBO
From $291 per night (USD)Expedia
Heart of Matlacha Studio-remodeled! NEW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
It's rare to find a place that's both historic and one-of-a-kind. It’s even rarer to find a place that is historic, uniq ...
From $291 per night (USD)Expedia
From $1004 per night (USD)VRBO
A Beachfront Oasis - Set Sail at the SS. Minnow!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome Aboard! The SS. Minnow is a classic Florida three-bedroom pool home that sits directly on the Gulf of Mexico wi ...
From $1004 per night (USD)VRBO
From $790 per night (USD)VRBO
HUGE LUXURY HOME ELEVATOR\/PRIVATE POOL&BEACH ACCESS\/CLUB AMENITIES INCLUDED\/PETS
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
CHECK OUT OUR LAST MINUTE RATES! PLEASE INQUIRE! GREAT RATES!!!! A WOW PROPERTY! WELCOME TO THE NEW AND SIMPLY AMAZING ...
From $790 per night (USD)VRBO
From $949 per night (USD)VRBO
Blue Heron * fish, boat, wine, dine, relax, repeat
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to the Blue Heron. This beautiful home will win your heart - a place to create amazing memories. Located in Boke ...
From $949 per night (USD)VRBO
From $125 per night (USD)VRBO
Island Escape 2
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a two bedroom, one bathroom, 950 sq. ft. apartment, located on the first floor of a duplex. It is situated on a ...
From $125 per night (USD)VRBO
From $714 per night (USD)VRBO
SeaStar North Captiva, Private Pool, Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Star is a exquisite new vacation beach home fully equipped and built to a high standard. The home is a spacious one ...
From $714 per night (USD)VRBO
From $121 per night (USD)VRBO
Studio Condo, just minutes from Charlotte Harbor and great island shopping!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Captains Cove waterfront end unit-Studio condo, 1 Bath, second floor, with parking under unit. Queen size Murphy bed an ...
From $121 per night (USD)VRBO
From $180 per night (USD)VRBO
Serenity abounds. Astounding sunsets, beautiful waters & perfect weather.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy easy living in a relaxed golf course community ....bike trails, nature walks, kayaking, boating, fishing, golf and ...
From $180 per night (USD)VRBO
From $504 per night (USD)VRBO
“Viva Captiva” - Vibrant beachfront home, 150 steps to the Gulf of Mexico
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
North Captiva Island remains a relatively undiscovered paradise, offering the laidback lifestyle that Florida used to be ...
From $504 per night (USD)VRBO
From $792 per night (USD)VRBO
The Silverseas Cottage - Charming, Immaculate with Private Pool - 2 Golf Carts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to the Silverseas Cottage, an immaculate and charming 3-bedroom, 2-bathroom vacation home on remote North Captiv ...
From $792 per night (USD)VRBO
From $438 per night (USD)Expedia
Holiday house Bokeelia for 1 - 8 persons with 3 bedrooms - Holiday house
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
ED Refnr. 3170641 This beautifully Tropical-appointed stilt house is located on Bokeelia with a view of Charlotte Harbo ...
From $438 per night (USD)Expedia
From $952 per night (USD)VRBO
Rum Cove: Private Heated Pool, Golf Cart, Docks, Airstrip & Sleeps 10
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
You'll have the entire home to yourself and will only share it with other guests in your party. This Island Treasure ha ...
From $952 per night (USD)VRBO
From $816 per night (USD)VRBO
The Barrancas Barnacle! A Private Canal-Front Island Oasis w\/ Dock, Sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A one-of-a-kind Private Water-Front Bokeelia Property! Enjoy over an acre of gulf-access island living with this rare r ...
From $816 per night (USD)VRBO
From $647 per night (USD)VRBO
Beach Please, North Captiva, FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This hidden gem is a breathtaking tropical paradise! North Captiva is accessible only by ferry, boat, jet ski, or small ...
From $647 per night (USD)VRBO
From $1372 per night (USD)VRBO
Beachfront 3-Bedroom Oasis on North Captiva Island
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
🏠 Charming Interior Design & Coastal Furnishings 🏖️ Private Beach w/ Loungers 🌴 Spectacular Bay Views & Sunrises! ☀️ ...
From $1372 per night (USD)VRBO
From $426 per night (USD)VRBO
Island Cottage in Quaint Matlacha Florida. Amazing island life is a click away…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy, 3 bedroom bungalow cottage is nestled on a peninsula located in the heart of Matlacha Florida. With the conve ...
From $426 per night (USD)VRBO
From $421 per night (USD)VRBO
THREE MASTER SUITES - POOL - WATERFRONT ON CORNER LOT - BOAT LIFT
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Update: Our beautiful home did receive about one inch of water with Hurricane Helene and Milton! But we are in the pro ...
From $421 per night (USD)VRBO
From $567 per night (USD)VRBO
New Tropical House in Bokeelia w\/pool,mooring post, access to the Gulf of Mexico
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This beautifully Tropical-appointed stilt house is located on Bokeelia with a view of Charlotte Harbor from across the ...
From $567 per night (USD)VRBO
From $580 per night (USD)VRBO
New Listing!! Dolphin Watch-3 Bedroom Beach Front on North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Our house is located directly on the beach! We are located on the northeast side of the island (the bay side just south ...
From $580 per night (USD)VRBO
From $217 per night (USD)VRBO
Lookout Cottage in Bokeelia! 2\/2 Cottage with Boat Trailer Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come visit the Lookout Cottage! This cottage has the old Florida charm perfect for a vacation rental in Bokeelia! Offeri ...
From $217 per night (USD)VRBO
From $749 per night (USD)VRBO
Paradise 3-BR 2-BA steps to the beach, private pool surrounded by nature!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hakuna Matata is located on the beautiful barrier island of North Captiva, just 3 miles off the coast of Southwest Flor ...
From $749 per night (USD)VRBO
From $690 per night (USD)VRBO
Linesider Hideaway Beach House - North Captiva Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to North Captiva Island and our home Linesider Hideaway. North Captiva is a barrier island to the west of the ma ...
From $690 per night (USD)VRBO
From $457 per night (USD)Expedia
Cozy Island home, pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This cozy home sits right in the middle of the island and is located in a cul de sac street making it very quiet and pri ...
From $457 per night (USD)Expedia
From $353 per night (USD)VRBO
6 Person 2-Bedroom Condo with Patio - Redfish - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated two-bedroom condo with private laundry, situated on the beautiful Gulf coast! With the ab ...
From $353 per night (USD)VRBO
From $836 per night (USD)Expedia
Solitude North Captiva 2 Carts, Dock, Private Pool, Club, Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Solitude is a unique North Captiva experience, in both location and layout. The perfect fit for large & multiple familie ...
From $836 per night (USD)Expedia
From $1752 per night (USD)VRBO
COME TOGETHER - consist of 2 Homes \"ALL YOU NEED IS FUN\" & \"HERE COMES THE FUN\"
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
Bring the whole family to this great place with lots of room for fun. COME TOGETHER consist of ALL YOU NEED IS FUN & HER ...
From $1752 per night (USD)VRBO
From $289 per night (USD)Expedia
6 Person 1-Bedroom Condo with Waterview Balcony - Lighthouse - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated one-bedroom condo with a balcony, situated on the beautiful Gulf coast! With the ability ...
From $289 per night (USD)Expedia
From $238 per night (USD)VRBO
4 Person 1 Bedroom Condo with Waterview Balcony- Dolphin - 4 Person 1 Bedroom Condo with Waterview Balcony - Dolphin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our stunning one-bedroom condo room with a balcony! Imagine waking up to breathtaking views every morning, an ...
From $238 per night (USD)VRBO
From $264 per night (USD)VRBO
Paradise on Franzone HEATED POOL & OUTDOOR BAR
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Hurricane Ian Updated Description: Hurricane Ian hit Pine Islands very hard. The property has been getting som ...
From $264 per night (USD)VRBO