Calusa Land Trust and Nature Preserve of Pine Island Rentals
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $347 per night (USD)Expedia
Gorgeous & Spacious 3\/3.5, Incredible Water Views! Sleeps 9!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
Incredible 3 bedroom 2.5 bath home with endless water views! This brand new renovated home offers so much space for the ...
From $347 per night (USD)Expedia
From $224 per night (USD)VRBO
Tranquility in St. James City! 2\/2 Overlooking Mangroves!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover tranquility in this charming 2-bedroom, 2-bath home nestled among lush mangroves. Enjoy a fully stocked kitchen ...
From $224 per night (USD)VRBO
From $185 per night (USD)Expedia
2\/2 Property in St. James City, Pet Friendly, Fenced in Yard!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Charming 2/2 in St. James City with plenty of space to park a boat trailer and is pet friendly! Both rooms offering quee ...
From $185 per night (USD)Expedia
From $1686 per night (USD)VRBO
Gulf-Front w\/ Heated Pool, Hot Tub & Golf Carts
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: 🌊 Gulf Front Paradise 🏊♂️ Heated Saltwater Pool: Lounge in your private beachside oasis. 🌅 Hot Tub Bliss: ...
From $1686 per night (USD)VRBO
From $349 per night (USD)Expedia
Bananarama! A 3bd2ba house in Saint James City 2 mins to open water w13k lift.
- Bedrooms:
- 2
- 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 $349 per night (USD)Expedia
From $178 per night (USD)VRBO
Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a relaxing stay at this lovely 2-bedroom house in Matlacha. The house features 2 queen beds, 2 bathrooms with a ha ...
From $178 per night (USD)VRBO
From $274 per night (USD)Expedia
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 $274 per night (USD)Expedia
From $152 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 $152 per night (USD)VRBO
From $233 per night (USD)Expedia
4\/2 Off Water Property in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4/2 Off Water Home in St. James City! This 4 bedroom 2 bathroom homes offers a ton of space for the entire family with a ...
From $233 per night (USD)Expedia
From $155 per night (USD)VRBO
Charming Waterfront Cottage on peaceful Matlacha! FULL RENOVATION DECEMBER 2024
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a fisherman’s paradise in picturesque Matlacha. This charming vacation rental offers a cozy retreat for guests ...
From $155 per night (USD)VRBO
From $166 per night (USD)Expedia
Welcome to Angler's Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our angler's paradise! This 2 Bedroom and 2 Bath retreat is tailored for the fishermen and fishing tournamen ...
From $166 per night (USD)Expedia
From $293 per night (USD)VRBO
Boaters Paradise in Matlacha Florida
- Bedrooms:
- 3
- 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 $293 per night (USD)VRBO
From $117 per night (USD)Expedia
Paradise on the water w\/ a pool & great fishing!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A fishing and boating paradise! ~You're on Island Time~ A beautiful, professionally decorated waterfront condo in St. ...
From $117 per night (USD)Expedia
From $111 per night (USD)VRBO
Slice of Paradise on Pine Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in a peaceful, quiet, & private wooded area. Perfect for indulging in the laid-back island lifestyle with old Fl ...
From $111 per night (USD)VRBO
From $901 per night (USD)Expedia
The Secret Island Retreat Heated Pool Open Water
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a d ...
From $901 per night (USD)Expedia
From $189 per night (USD)VRBO
Charming 2-bedroom house in beautiful Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our charming retreat in Bokeelia, FL. Nestled on Pine Island, this cozy getaway offers a serene escape with b ...
From $189 per night (USD)VRBO
From $214 per night (USD)VRBO
Charming waterfront home in Saint James City on Main Canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Island Blues Charming Home! Welcome to our tranquil Island Blues home with beautiful canal views and direct access to ...
From $214 per night (USD)VRBO
From $181 per night (USD)VRBO
Relax on Island Time In This 2 Bed \/ 1 Bath Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Saint James City, FL, and unwind in this charming 2-bedroom home near Tropical Point Park. Enjoy an open kitch ...
From $181 per night (USD)VRBO
From $175 per night (USD)Expedia
Captain`s Harbor Condo 2\/2 on the Water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy nature at its finest from the screened in porch of this beautiful 2 bedroom 2 bathroom Condo. This spacious condo ...
From $175 per night (USD)Expedia
From $362 per night (USD)VRBO
Gorgeous 3\/3 W\/ Downstairs Suite! Pool Home! Boat Lift!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Gorgeous 3/3 pool home with suite downstairs! This newly renovated home offers 2 bedrooms upstairs with a den that has a ...
From $362 per night (USD)VRBO
From $278 per night (USD)Expedia
Florida Style Villa by the Water with heated Pool, Dock, Gulf access!
- 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 $278 per night (USD)Expedia
From $720 per night (USD)VRBO
Treetop getaway on a secluded Island with gulf coast beaches
- Bedrooms:
- 2
- 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 $720 per night (USD)VRBO
From $551 per night (USD)Expedia
Charming 2-bedroom house Welcome to Cay Cove Retreat, your serene getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Cay Cove Retreat, your serene getaway nestled at MATLACHA! This charming home offers the perfect blend of com ...
From $551 per night (USD)Expedia
From $189 per night (USD)VRBO
Snook\/Sheephead @ 2 Fish Inn Waterside Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
The Snook/Sheephead @ the 2 Fish Inn offers an exceptional retreat for those seeking to explore the abundant charms of P ...
From $189 per night (USD)VRBO
From $184 per night (USD)Expedia
Cabana @ 2 Fish Inn Pool Side
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Are you searching for your slice of island paradise while on vacation? Look no further than the 2 Fish Inn Cabana in St. ...
From $184 per night (USD)Expedia
From $497 per night (USD)VRBO
Luxurious waterfront home, pool, boat dock, filet 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 $497 per night (USD)VRBO
From $406 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 $406 per night (USD)Expedia
From $357 per night (USD)VRBO
Gorgeous 3\/2 Pool Home in St. James City, Incredible Water Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Brand new and gorgeous pool home in St. James City! This property offers 3 bedrooms, primary bedroom offering a king siz ...
From $357 per night (USD)VRBO
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 $302 per night (USD)VRBO
Charming 2-bedroom house in quaint Matlacha with WiFi, AC, POOL and Boat Lift
- 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 $302 per night (USD)VRBO
From $250 per night (USD)Expedia
3-bedroom pool house in charming Bokeelia with AC, WiFi. Beautiful, peaceful,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Your Bokeelia adventure begins at this 3-bedroom pool house. With 1 king bed and 2 queen beds, this phenomenal property ...
From $250 per night (USD)Expedia
From $284 per night (USD)VRBO
Charming 2-bedroom house in delightful Matlacha with WiFi, AC
- 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 $284 per night (USD)VRBO
From $325 per night (USD)Expedia
Brand New Build, 3\/3 Heart of Bokeelia! Boat Ramp Across the Street!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Cracker Jacks! Discover this stunning brand-new build located in the heart of beautiful Bokeelia! Perfectly d ...
From $325 per night (USD)Expedia
From $171 per night (USD)VRBO
Peaceful fishing Island paradise with boat lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our island getaway home is situated at the northwest end of Pine Island (off of FT Myers/ Cape Coral) in the community o ...
From $171 per night (USD)VRBO
From $745 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 $745 per night (USD)Expedia
From $706 per night (USD)VRBO
Pearl of the Island for 2, Cayo Costa
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This phenomenal beach house on Cayo Costa is the perfect home base for your trip. With 1 fabulous bedroom featuring a qu ...
From $706 per night (USD)VRBO
From $466 per night (USD)Expedia
Charlie's of Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Charlie's of Bokeelia on Pine Island – Your Perfect Home Island Escape This marvelous Bokeelia home offers e ...
From $466 per night (USD)Expedia
From $1004 per night (USD)VRBO
\" Here Comes The Fun\" Absolutely Magnificent! Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
HERE COMES THE FUN! Doo-d-Doo-Doo FUN FUN FUN HERE IT COMES! No detailed has been missed. This is truly a luxury home. ...
From $1004 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $391 per night (USD)VRBO
Modern Renovation~Club Pool👙 Kayaks🛶 Golf Cart🚙 Boat Dock⛵️ Private Beach🏖️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A true gem tucked away off the coast of Florida, North Captiva, also known as Upper Captiva Island is an adventure to ge ...
From $391 per night (USD)VRBO
From $266 per night (USD)Expedia
Treasure Cove Serenity! 3\/2 with Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly built home has everything you need to make your stay in St. James City perfect. Brand new appliances and furn ...
From $266 per night (USD)Expedia
From $214 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 $214 per night (USD)VRBO
From $211 per night (USD)Expedia
New waterfront Pine Island home awaits your fishing adventure!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our newly constructed waterfront house on Pine Island, located in the serene Charlotte Shore area of Bokeelia, FL, is n ...
From $211 per night (USD)Expedia
From $270 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 $270 per night (USD)VRBO
From $160 per night (USD)Expedia
2\/2 Cherry Estates Vacation Perfection
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***POOL COMING SOON*** Your next getaway awaits at the beautiful Cherry Estates in St. James City, FL. Our inviting 2-b ...
From $160 per night (USD)Expedia
From $278 per night (USD)VRBO
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 $278 per night (USD)VRBO
From $276 per night (USD)Expedia
2\/2 Waterfront home with pool and docking for a vessel.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A gorgeous 2-bedroom, 2-bathroom mobile home in the picturesque St. James City, FL. This charming retreat offers a perfe ...
From $276 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 $182 per night (USD)Expedia
2 bed\/ 2.5 bath Waterfront Condo with 2 pools and great fishing
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the ultimate comfort and relaxation at this beautifully remodeled garden front condo. With its inviting ambia ...
From $182 per night (USD)Expedia
From $76 per night (USD)VRBO
1 bedroom,1 bath condo, Community heated pool and dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the perfect Winter getaway in Saint James City, FL with our inviting 1-bedroom, 1-bathroom condo. Located in a ...
From $76 per night (USD)VRBO
From $187 per night (USD)Expedia
2\/2.5 condo with docking available for your boat and pools for soaking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the picturesque shores of Charlotte Harbor and experience a vacation like no other. This stunning 2-bedroom, 2 ...
From $187 per night (USD)Expedia
From $327 per night (USD)VRBO
Terrific vacation home on quiet Clipper Lane 2\/2 pool home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Escape to this remarkable vacation home nestled on peaceful Clipper Lane, just off Sanibel Blvd., in the charming town o ...
From $327 per night (USD)VRBO
From $361 per night (USD)Expedia
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 $361 per night (USD)Expedia
From $372 per night (USD)VRBO
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 $372 per night (USD)VRBO
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 $175 per night (USD)VRBO
Waterfront condo with easy water access to world class fishing and sightseeing.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully appointed waterfront condo boasting two bedrooms and 2 1/2 baths in a quaint island atmosphere. Enjoy the fa ...
From $175 per night (USD)VRBO
From $228 per night (USD)Expedia
Charming 3\/2 in St. James City, Waterfront!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3/2 in located in the heart of St. James City! Nestled on a quiet corner, on a large lot offering so much ...
From $228 per night (USD)Expedia
From $331 per night (USD)VRBO
Villa Papaya in St James city !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your island getaway in the charming community of St. James City! This vacation rental home offers the perfect ...
From $331 per night (USD)VRBO
From $254 per night (USD)Expedia
3\/3 Amazing Heated Pool Home in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom 3 bathroom home off water with an heated amazing pool! Recently upgraded including a beautiful kitch ...
From $254 per night (USD)Expedia
From $152 per night (USD)VRBO
Breakaway in Bokeelia!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Forget your worries in this spacious, serene home. Enjoy family, friend or alone time in this well thought out floor pl ...
From $152 per night (USD)VRBO
From $337 per night (USD)Expedia
Stunning home ready for your enjoyment, New pool 2024. Bokeelia, Pine Island
- 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 $337 per night (USD)Expedia
From $389 per night (USD)VRBO
Island Life! Great Fishing - Unique 2 Home Property w\/Heated Pool -Tropical Breeze Villa 1 - Roelens
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Tropical Breeze Villa 1 Welcome to your island getaway! Nestled on Pine Island, this property offers a luxurious main ...
From $389 per night (USD)VRBO
From $319 per night (USD)Expedia
Island Life! Great Fishing - Unique Home with Heated Pool - Tropical Breeze Villa Main- Roelens
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical Breeze Villa Main Welcome to your island getaway! Nestled on Pine Island, this main house provides ample acco ...
From $319 per night (USD)Expedia
From $168 per night (USD)VRBO
Welcome to Island Vibes with a Modern Touch! Come enjoy Pine Island.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Relaxing property inside and out! Space for your family to enjoy the home and yard! Sitting out back during the day or n ...
From $168 per night (USD)VRBO
From $245 per night (USD)Expedia
Cozy Cottage on Direct Access Canal with Boat Lift
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Waterman is a newly remodeled 2 bedroom, 1 bath stilt bungalow. Located on the Monroe Canal, this home is perfect fo ...
From $245 per night (USD)Expedia
From $739 per night (USD)VRBO
Tipsy Turtle: Fun for everyone! Pool & Golf Carts
- 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 $739 per night (USD)VRBO
From $773 per night (USD)Expedia
Private beach oasis -- 2-minute walk to the ocean! w\/ Golf Cart & Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The first thing you See or should we say "Sea" is the breathtaking Gulf of Mexico from virtually everywhere from each r ...
From $773 per night (USD)Expedia
From $485 per night (USD)VRBO
“Coral Cottage”<br>A Cottage Secluded in Palms with a Jacuzzi 2 minute walk 2 Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, ...
From $485 per night (USD)VRBO
From $242 per night (USD)Expedia
The Blue Lagoon With Heated Pool \/on the Canal With NEW Boat Lift and Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please come and enjoy our 2BR / 2BA 1410 Sq ft. POOL home located in the quaint fishing village of Matlacha. ...
From $242 per night (USD)Expedia
From $652 per night (USD)VRBO
The Salty Snook
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unique Gulf Front and View Home : Private Dockage for up to 30 Foot Boat available...Perfect Florida Fishing Get Away. ...
From $652 per night (USD)VRBO
From $1016 per night (USD)Expedia
Captiva Beach Sunset Gulf Front Pool NCIC Carts Remodeled Feb Rate $650\/Nt Deal!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 17
Captiva Beach Sunset 5 BR/4.5 BA | Sleeps 15 in beds (plus 2 twin recliners, perfect for kids!) | Beachfront | Private P ...
From $1016 per night (USD)Expedia
From $149 per night (USD)VRBO
Mermaid Waterfront Hideaway Great fishing, kayaking, boat lift available too!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Florida home on the water. Located in quaint little village of St. James City, this property is away from the t ...
From $149 per night (USD)VRBO
From $218 per night (USD)Expedia
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
- Bedrooms:
- 3
- 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 $218 per night (USD)Expedia
From $666 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 $666 per night (USD)VRBO
From $506 per night (USD)Expedia
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Find your ideal vacation home that fisherman and their wives love to bring their familys and vacation in Matlacha.Plenty ...
From $506 per night (USD)Expedia
From $292 per night (USD)VRBO
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 $292 per night (USD)VRBO
From $432 per night (USD)Expedia
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 $432 per night (USD)Expedia
From $256 per night (USD)VRBO
3 Minutes to Open Water! Great Fishing Retreat on Gulf-Access Canal! Over $125 Free Daily Activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Tarpon Camp in beautiful Bokeelia, FL - your own private retreat in the heart of the Tarpon Capital of the Wo ...
From $256 per night (USD)VRBO
From $451 per night (USD)Expedia
8 Person 2-Bedroom Condo with Waterview Balcony - Tarpon - Welcome to our stunning two-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our stunning two-bedroom condo room with a balcony! Imagine waking up to breathtaking views every morning, an ...
From $451 per night (USD)Expedia
From $340 per night (USD)VRBO
Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nice relaxing townhome…. Simple, white, clean…. A few steps from the harbors edge. Great place to escape from work, or ...
From $340 per night (USD)VRBO
From $251 per night (USD)VRBO
Waterfront Gulf Access- Just a few minutes to Big Water.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
The San Carlos Bay is across the street. If it's fishing and boating you want then this home could be perfect for you. B ...
From $251 per night (USD)VRBO
From $400 per night (USD)VRBO
Bokeelia Island Oasis: Waterfront, Private Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Get a taste of island living at this delightful 3-bedroom, 3-bath Bokeelia escape! Ideally located at the tip of Pine Is ...
From $400 per night (USD)VRBO
From $982 per night (USD)Expedia
Brand New Luxury beach home! All new inside! HUGE 5 BD 5 BA 9 beds! Sleeps 16+!
- Bedrooms:
- 5
- 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 $982 per night (USD)Expedia
From $120 per night (USD)VRBO
Quiet and Cozy Island Retreat. Beautifully Remodeled.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Enjoy your privacy and peace at our recently renovated Bokeelia Get-Away. This Vacation home is designed for two with r ...
From $120 per night (USD)VRBO
From $264 per night (USD)Expedia
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $264 per night (USD)Expedia
From $329 per night (USD)VRBO
Game Room & Deck: Spacious Home in St James City
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Palm trees, warm weather, chic interior, oh my! Take that much-needed break from your day-to-day and travel to the islan ...
From $329 per night (USD)VRBO
From $169 per night (USD)Expedia
Small home in Paradise.. spend your vacation without a lot of hustle & bustle.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This property is off the beaten path with many amenities & short distance to some of the most beautiful beaches. Home is ...
From $169 per night (USD)Expedia
From $135 per night (USD)VRBO
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 $135 per night (USD)VRBO
From $294 per night (USD)Expedia
Waterfront cottage in Matlacha, FL -<br>Unavailable at this time due to Hurr Ian.🌴
- Bedrooms:
- 2
- 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)Expedia
From $453 per night (USD)VRBO
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)VRBO
From $293 per night (USD)VRBO
The Perfect Day in Matlacha! Direct Gulf Access!
- Bedrooms:
- 3
- 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 $293 per night (USD)VRBO
From $337 per night (USD)VRBO
Relaxing Island View! Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a newer home with a spectacular view of the water. We are on a large bridged island that is very laid back and ...
From $337 per night (USD)VRBO
From $816 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
Inquire about last minute April specials! SPACIOUS 4 BR. 3 BATH - sleeps 12 in beds, 2 Golf Carts, PRIVATE HEATED POOL ...
From $816 per night (USD)VRBO
From $203 per night (USD)VRBO
Sunset Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Matlacha, it’s a water sports paradise! World class fishing, boating, kayaking, beautiful sunrises and sunsets! See natu ...
From $203 per night (USD)VRBO
From $840 per night (USD)Expedia
Butterfly Breeze on North Captiva Island, Ask About Special Fall and Low Occupancy Rates
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to your own slice of island paradise at Butterfly Breeze – a luxurious retreat just moments away from the beach o ...
From $840 per night (USD)Expedia
From $340 per night (USD)VRBO
North Captiva waterfront Townhome with dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sea Turtle townhouse is a beautifully decorated three bedroom townhouse located in Safety Harbor Club on the unspoil ...
From $340 per night (USD)VRBO
From $354 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 $354 per night (USD)Expedia
From $1067 per night (USD)VRBO
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 $1067 per night (USD)VRBO
From $150 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 $150 per night (USD)Expedia