Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $281 per night (USD)VRBO
Peaceful, Family friendly Home w Pool, dock space & quick access to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful & Fun Family friendly home with 3 bedrooms enough to sleep 8 comfortably. There is an entertainment area with ...
From $281 per night (USD)VRBO
From $811 per night (USD)Expedia
Gorgeous & Spacious 3\/3.5, Incredible Water Views! Sleeps 9!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Incredible 3 bedroom 2.5 bath home with endless water views! This brand new renovated home offers so much space for the ...
From $811 per night (USD)Expedia
From $395 per night (USD)VRBO
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 $395 per night (USD)VRBO
From $213 per night (USD)Expedia
Charming Waterfront Cottage on peaceful Matlacha!
- 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 $213 per night (USD)Expedia
From $353 per night (USD)VRBO
3 BR with Decks and Privacy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this tranquil 3-bedroom house on a quiet street enveloped by lush trees, offering ultimate privacy for your dr ...
From $353 per night (USD)VRBO
From $172 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 $172 per night (USD)VRBO
From $265 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 $265 per night (USD)VRBO
From $288 per night (USD)Expedia
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 $288 per night (USD)Expedia
From $136 per night (USD)VRBO
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 $136 per night (USD)VRBO
From $452 per night (USD)Expedia
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 $452 per night (USD)Expedia
From $401 per night (USD)VRBO
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 $401 per night (USD)VRBO
From $512 per night (USD)Expedia
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 $512 per night (USD)Expedia
From $380 per night (USD)VRBO
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 $380 per night (USD)VRBO
From $168 per night (USD)Expedia
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)Expedia
From $245 per night (USD)VRBO
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)VRBO
From $222 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 $222 per night (USD)Expedia
From $305 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 $305 per night (USD)VRBO
From $127 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 $127 per night (USD)Expedia
From $135 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 $135 per night (USD)VRBO
From $171 per night (USD)Expedia
Cozy Matlacha Waterfront 1 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Fish from the backyard. Walk to shops & restaurants. Centrally located cozy waterfront getaway. Just a short walk to the ...
From $171 per night (USD)Expedia
From $953 per night (USD)VRBO
The Secret Island Retreat HeatedPool\/4b\/open water
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a d ...
From $953 per night (USD)VRBO
From $466 per night (USD)Expedia
Private Villa, 3 King Beds, Pool, Elevator, close to Ferry for Barrier Islands
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Palm Tree Villa on Pine Island, located on South-West Florida's Gulf of Mexico Coast. This spacious 3400 sq f ...
From $466 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 $255 per night (USD)VRBO
Castaways in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the vibrant hues of Matlacha, Florida, this whimsical 2-bedroom cottage is a tropical haven. Adorned in charm ...
From $255 per night (USD)VRBO
From $337 per night (USD)VRBO
Hemingway-esque Florida Escape, Boat and Available Boat Lift On Property,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming vacation home nestled in the heart of Matlacha, Florida – the artsiest fishing town in the Sunsh ...
From $337 per night (USD)VRBO
From $162 per night (USD)Expedia
Island Romp is a tiny home in walking distance to local eateries and shops!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a tiny home located on a canal in Matlacha, FL. Matlacha is the gateway to Pine Island and is home to fishermen ...
From $162 per night (USD)Expedia
From $180 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 $180 per night (USD)VRBO
From $412 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 $412 per night (USD)Expedia
From $263 per night (USD)VRBO
2\/2 Heart of Pine Island Home, with Wrap Around Porch!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming 2 bedroom 2 bathroom home is located in the heart of Pine Island! This home offers two master suites, one ...
From $263 per night (USD)VRBO
From $232 per night (USD)Expedia
Redfish Retreat - Beautiful 3\/2 on Water with Boat Ramp on Property!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 3
Welcome to Florida Charm! This 3 bedroom 2 bath spacious home has everything you need for an island getaway! Bring your ...
From $232 per night (USD)Expedia
From $290 per night (USD)VRBO
Key West Style Home w\/ Hot Tub and Boat Lift in the Heart of Matlacha!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two-story Key West style stilted home in the heart of Matlacha! You will have the home to yourself! The first floor is i ...
From $290 per night (USD)VRBO
From $323 per night (USD)Expedia
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 $323 per night (USD)Expedia
From $326 per night (USD)VRBO
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 $326 per night (USD)VRBO
From $136 per night (USD)Expedia
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 $136 per night (USD)Expedia
From $383 per night (USD)VRBO
Stunning home ready for your enjoyment, New pool 2024. Bokeelia, Pine Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sonny 2 Palms. This Direct Gulf Access Home has been completely remodeled in fall of 2021. This home offers: ...
From $383 per night (USD)VRBO
From $269 per night (USD)Expedia
Key West style waterfront home w\/ Dock- Pineisland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located at the very north end of PineIsland, our beautiful canal access home is a boaters or stay-vacationers dream home ...
From $269 per night (USD)Expedia
From $401 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 $401 per night (USD)VRBO
From $641 per night (USD)Expedia
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)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 $350 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 $350 per night (USD)Expedia
From $253 per night (USD)VRBO
Snook\/Sheephead @ 2 Fish Inn
- 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 $253 per night (USD)VRBO
From $253 per night (USD)Expedia
Cabana @ 2 Fish Inn: 1 BR, 1 BA Lodge in Saint James City, Sleeps 4
- 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 $253 per night (USD)Expedia
From $300 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 $300 per night (USD)VRBO
From $79 per night (USD)Expedia
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 $79 per night (USD)Expedia
From $413 per night (USD)VRBO
Welcome to Historic Pineland Florida, Island time really does start here.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a little slice of Old Florida. If you are looking for a peaceful place to relax and unwind this is the place ...
From $413 per night (USD)VRBO
From $567 per night (USD)Expedia
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 $567 per night (USD)Expedia
From $535 per night (USD)VRBO
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 $535 per night (USD)VRBO
From $359 per night (USD)Expedia
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 $359 per night (USD)Expedia
From $269 per night (USD)VRBO
Treasure Cove Serenity! 3\/2 with Boat Lift, Beautiful New Home!
- 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 $269 per night (USD)VRBO
Click For PricingExpedia
Dream Island Home Sum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover Pine Island, Florida's hidden gem, in this spacious home boasting high-end finishes. Explore the sceni ...
Click For PricingExpedia
From $244 per night (USD)VRBO
Peaceful retreat. Fishing Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
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 $244 per night (USD)VRBO
From $173 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 $173 per night (USD)Expedia
From $168 per night (USD)VRBO
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 $168 per night (USD)VRBO
From $320 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 $320 per night (USD)Expedia
From $313 per night (USD)VRBO
2\/2 Waterfront home with pool and boat lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A gorgeous 2-bedroom, 2-bathroom mobile home located in the picturesque St. James City, FL. This charming retreat offers ...
From $313 per night (USD)VRBO
From $435 per night (USD)Expedia
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 $435 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $137 per night (USD)Expedia
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 $137 per night (USD)Expedia
From $202 per night (USD)VRBO
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 $202 per night (USD)VRBO
From $311 per night (USD)Expedia
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 $311 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 $242 per night (USD)Expedia
Charming & sun-filled condo with pool, W\/D, AC, & balcony - steps from the beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Bokeelia Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $242 per night (USD)Expedia
From $389 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 $389 per night (USD)VRBO
From $262 per night (USD)VRBO
Immaculate Waterfront Home With Heated Pool. Pet Friendly.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to St. James City on historic Pine Island to enjoy this beautifully renovated 2 bedroom canal home with a gorgeou ...
From $262 per night (USD)VRBO
From $912 per night (USD)VRBO
ABSOLUTELY MAGNIFICENT! BEACH HOME PRIVATE POOL 2 GOLF CARTS\nHERE COMES THE FUN!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
HERE COMES THE FUN! Doo-d-doo-doo FUN FUN FUN Here it Comes! is a new single story 3-bedroom, 3 bathroom home. Finished ...
From $912 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 $1457 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 $1457 per night (USD)VRBO
From $396 per night (USD)VRBO
SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Golf Cart-Sleeps 7
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
*SUMMER DISCOUNT & DATES AVAILABLE* SMUGGLERS HIDEAWAY is a secluded 3 bedroom island home located on North Captiva Isl ...
From $396 per night (USD)VRBO
From $162 per night (USD)VRBO
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 $162 per night (USD)VRBO
From $471 per night (USD)Expedia
Stunning canal-front home with pools, AC, W\/D & hammock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Bocilla Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $471 per night (USD)Expedia
From $138 per night (USD)VRBO
Has all of the modern comforts-hidden in the palm and mango groves.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for those seeking a peaceful retreat or just to get away for some time alone. This original Florida cracker-styl ...
From $138 per night (USD)VRBO
From $243 per night (USD)Expedia
Pelican`s Preserve in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this beautiful 2 bedroom 2 bath with a screened lanai and an open deck to enjoy views of the canal. King bedroom i ...
From $243 per night (USD)Expedia
From $283 per night (USD)VRBO
3\/2 Heated Pool Home on the Water in St. James City! No Hurricane Damage!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
*No Hurricane Helene or Milton Damage* Fresh and airy pool home on the water in St. James City! This property offers 3 b ...
From $283 per night (USD)VRBO
From $317 per night (USD)Expedia
2\/2 Pool Home on the Water, Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come and truly enjoy what Florida living is all about. This newly remodeled two bedroom 2 bathroom home is a pleasure to ...
From $317 per night (USD)Expedia
From $258 per night (USD)VRBO
RENTAL READY! Newly Renovated 2\/2 POOL Home with BOAT LIFT, INCREDIBLE ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Banana Haven! This immaculate, newly renovated 2 bedroom, 2 bathroom home is waterfront with direct access to ...
From $258 per night (USD)VRBO
From $206 per night (USD)Expedia
2\/2 Privacy in Pine Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Pineland is one of the most unique areas on Pine Island. It is beautiful and features the Randell Research Center which ...
From $206 per night (USD)Expedia
From $302 per night (USD)VRBO
Welcome to Porchfish! 3\/2 in St. James City! Boat lift & Beautiful Views! No Hurricane Damage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*No Hurricane Damage* Welcome to peace, welcome to paradise, welcome to PORCHFISH! This beautiful 3 bedroom, 2 bath home ...
From $302 per night (USD)VRBO
From $714 per night (USD)Expedia
Island Daze: Modernized Kitchen and Endless Relaxation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whether you plan to fish, beach-comb, relax in the sun, play in the pool, enjoy nature or do nothing this is your ideal ...
From $714 per night (USD)Expedia
From $283 per night (USD)VRBO
Tropical Island Resort Nestled on the Gulf Coast of Southwest Florida
- Bedrooms:
- 3
- 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 $283 per night (USD)VRBO
From $494 per night (USD)Expedia
CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning waterfront property in Safety Harbor Club. Enjoy breathtaking views and the best the island has to offer at Cap ...
From $494 per night (USD)Expedia
From $1164 per night (USD)VRBO
Tropical Family Oasis: Pool, Spa, Golf Cart
- 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 $1164 per night (USD)VRBO
From $425 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 If you're looking for a fabulous waterfront vacation home with a private poo ...
From $425 per night (USD)VRBO
From $439 per night (USD)VRBO
Guardalavaca , Boaters Paradise and Beachgoers Delight , New Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Salutations from the balcony in this secluded townhome as you watch the sunrise and breathe fresh ocean air. Come a ...
From $439 per night (USD)VRBO
From $313 per night (USD)Expedia
Tropical Paradise! Gorgeous 3\/3 Pool Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Zuzu's Fancy is a wonderful 3 bedroom, 3 bathroom home in a quiet St. James City neighborhood. This home is sure to ple ...
From $313 per night (USD)Expedia
From $217 per night (USD)VRBO
Waterfront Matlacha Condo w\/ Patio + Pool Access!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience an 'Island Getaway' at this 2-bedroom, 2.5-bath end-unit condo in Matlacha! Nestled in a tropical landscape, ...
From $217 per night (USD)VRBO
From $1426 per night (USD)Expedia
Island Queen, Luxury in Paradise, 200ft to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
If you are looking for the best pool and beach location, the Island Queen should be your next vacation destination! This ...
From $1426 per night (USD)Expedia
From $613 per night (USD)VRBO
Matlacha\/Cape Coral - Kokopelli House - relax, it's your Island lifestyle
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three-story SW facing residence offers unsurpassed views of the bay. Put yourself on Island time in this beautifu ...
From $613 per night (USD)VRBO
From $812 per night (USD)Expedia
Private dock with 2 golf carts Oceanfront home Absolute Best Location on island!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
All brand new. Complete remodel. Be the 1st guest in. Located overlooking Safety Harbor. 2 Amazing decks overlooking the ...
From $812 per night (USD)Expedia
From $253 per night (USD)VRBO
THREE Minutes to Open Water! Fantastic, Remodeled Fishing Retreat on Gulf-Access Canal, Free Wifi!
- 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 $253 per night (USD)VRBO
From $353 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 $353 per night (USD)Expedia
From $213 per night (USD)VRBO
Bokeelia Cottage w\/ Private Pool & Tiki Bar!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Find a tropical paradise in your own backyard at this 2-bedroom, 2-bathroom Bokeelia vacation rental cottage! With all o ...
From $213 per night (USD)VRBO
From $1011 per night (USD)Expedia
Manatee Manor: Your Ultimate Beachfront Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Directly on the beach in one of North Captiva's most exclusive locations, this architectural delight is truly a great pl ...
From $1011 per night (USD)Expedia
From $1452 per night (USD)VRBO
The Green Flash: Gulf Front Home with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Discover Paradise Reimagined: The Newly Renovated Green Flash on North Captiva Island **Pool and Outdoor Kitchen are cu ...
From $1452 per night (USD)VRBO
From $868 per night (USD)Expedia
Island Splash: Private Pool and Air hockey, Fun for the Whole Family
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
082 - Island Splash is a fabulous 5 bedroom home was designed to accommodate groups up to 12 in comfort! With lots of ro ...
From $868 per night (USD)Expedia
From $905 per night (USD)VRBO
Dolphin Cottage: Beachfront Home With Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Dolphin Cottage, an awesome 2-bedroom Bayfront home Just steps to your own private beach. Best fishing spot on the islan ...
From $905 per night (USD)VRBO
From $739 per night (USD)Expedia
128 - Shell Yeah! North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Upon arriving at Shell Yeah, your senses will be immediately captivated by the enchanting downstairs area, featuring a s ...
From $739 per night (USD)Expedia
From $686 per night (USD)VRBO
Flamingo House: Gulfside Getaway with Pool, Karaoke & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flamingo House is a lovely tropical home with a special island flair. Carved flamingos on the eaves, conch shells, pinea ...
From $686 per night (USD)VRBO
From $1403 per night (USD)Expedia
Key Lime Time: Private Pool and Panoramic Gulf Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 169 - Key Lime Time, a stunning 5 bedroom, pool home with breathtaking Gulf views on North Captiva Island. Th ...
From $1403 per night (USD)Expedia
From $769 per night (USD)VRBO
Coconut Castaway-Ocean Views, Golf Cart, Club Pool, Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coconut Castaway, your idyllic beach retreat on North Captiva Island! Accessible only by ferry or water taxi, ...
From $769 per night (USD)VRBO
From $225 per night (USD)Expedia
Pet-Friendly Oasis w\/ Deck & Fire Pit in Bokeelia!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Hitch up your boat, gather the family, and embark on an unforgettable Florida adventure to this luxurious vacation renta ...
From $225 per night (USD)Expedia