
Calusa Land Trust and Nature Preserve of Pine Island Rentals

- From $182 per night (USD)
VRBO
**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 $182 per night (USD)VRBO
- From $446 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 $446 per night (USD)Expedia
- From $232 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 $232 per night (USD)VRBO
- From $279 per night (USD)
Expedia
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 $279 per night (USD)Expedia
- From $611 per night (USD)
VRBO
Waterfront home with private pool, dock, patio, balconies, & bikes
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Maison de Sirens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $611 per night (USD)VRBO
- From $475 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 $475 per night (USD)Expedia
- From $549 per night (USD)
VRBO
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 $549 per night (USD)VRBO
- From $1450 per night (USD)
Expedia
BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL
- 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 $1450 per night (USD)Expedia
- Click For Pricing
VRBO
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 $952 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 $952 per night (USD)Expedia
- From $679 per night (USD)
VRBO
Panoramic Ocean Views, Sleeps 10, Heated pool, 2 Golf Carts
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A few April dates are open and have been deeply discounted, book now to secure savings! Featuring a private heated pool ...
From $679 per night (USD)VRBO
- From $402 per night (USD)
Expedia
Heated Pool + Lanai: Matlacha Isles Getaway
- 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
- Click For Pricing
VRBO
On-Site Canal Access: St James City Home
- 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 $924 per night (USD)
Expedia
\"All You Need Is Fun\" Stunning Beach Home-Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Make some memories at this unique and family-friendly place. Private home on North Captiva Island Florida. As beautiful ...
From $924 per night (USD)Expedia
- From $369 per night (USD)
VRBO
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 $369 per night (USD)VRBO
- From $729 per night (USD)
Expedia
Large home on private penninsula with waterfront and views on three sides.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
2,800 SF four bedroom waterfront home built in 2008. Located on private peninsula at the end of private road with water ...
From $729 per night (USD)Expedia
- From $705 per night (USD)
VRBO
Pirate's Captiva-Golf Cart and HOT Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Paradise!! Golf cart included with your rental. Pirates Captiva was built in 2018, and withheld Hurricane lan ...
From $705 per night (USD)VRBO
- From $141 per night (USD)
Expedia
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 $141 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $487 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 $487 per night (USD)Expedia
- From $490 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 $490 per night (USD)VRBO
- From $1107 per night (USD)
Expedia
Luxury Beachfront Home-Lit Fishing Dock, Shelling, Stunning Sunrises- Golf Cart
- 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 $1107 per night (USD)Expedia
- From $167 per night (USD)
VRBO
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 $167 per night (USD)VRBO
- From $159 per night (USD)
Expedia
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 $159 per night (USD)Expedia
- From $131 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 $131 per night (USD)VRBO
- From $752 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 RATE FOR ONE PRIME WEEK OPEN ********APRIL 11TH TO APRIL 18TH! INQUIRE ASAP!******* GREAT R ...
From $752 per night (USD)VRBO
- 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
- Click For Pricing
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 ...
Click For PricingExpedia
- From $105 per night (USD)
VRBO
Book 4 nights and pay only 3 - your dream vacation awaits!
- 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 $105 per night (USD)VRBO
- From $105 per night (USD)
Expedia
Your vacation, your price: book 4 nights and pay for only 3!
- 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 $105 per night (USD)Expedia
- From $109 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. Thanks to the conveni ...
From $109 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 $337 per night (USD)
VRBO
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 $337 per night (USD)VRBO
- From $278 per night (USD)
Expedia
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 and ...
From $278 per night (USD)Expedia
- From $479 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 $479 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 $940 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 $940 per night (USD)VRBO
- From $982 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 $982 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 $83 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 $83 per night (USD)VRBO
- From $432 per night (USD)
VRBO
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 $432 per night (USD)VRBO
- From $725 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 $725 per night (USD)VRBO
- From $489 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 $489 per night (USD)VRBO
- From $895 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 $895 per night (USD)VRBO
- From $538 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 $538 per night (USD)VRBO
- From $180 per night (USD)
Expedia
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 $180 per night (USD)Expedia
- From $676 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 $676 per night (USD)VRBO
- From $510 per night (USD)
Expedia
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 $510 per night (USD)Expedia
- From $430 per night (USD)
VRBO
THREE MASTER SUITES - POOL - WATERFRONT ON CORNER LOT - BOAT LIFT
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Our beautiful newly remodeled home away from home is located in St. James City, Florida. It was just remodeled from the ...
From $430 per night (USD)VRBO
- From $559 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 $559 per night (USD)VRBO
- From $444 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, situated on the beautiful Gulf coast! With the ability to sleep six gu ...
From $444 per night (USD)VRBO
- From $892 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 $892 per night (USD)Expedia
- From $1928 per night (USD)
VRBO
Come Together-consist of 2 Homes4 Golf Carts2 pool
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
COME TOGETHER consist of 2 fabulous homes right next to each other. ALL YOU NEED IS FUN & HERE COMES THE FUN is more spa ...
From $1928 per night (USD)VRBO
- From $647 per night (USD)
Expedia
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)Expedia
- From $229 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 $229 per night (USD)VRBO
- From $1389 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 $1389 per night (USD)VRBO
- From $134 per night (USD)
VRBO
Crab Cove Inn. 3\/2 Direct Gulf Access with 50 ft sea wall.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our 3-bedroom, 2-bathroom canal front home with a fully equipped kitchen. Enjoy dinner on the deck or in the d ...
From $134 per night (USD)VRBO