Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $272 per night (USD)
VRBO
Updated St. James City Home on Canal w\/Pool & Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Slip on your flip flops and grab your sunscreen, as this 4-bedroom, 2-bath Saint James City vacation rental awaits! The ...
From $272 per night (USD)VRBO
- From $149 per night (USD)
Expedia
A Florida Island, beautiful waterways, serenity!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“Something Fishy” is a newly remodeled, cozy, two bedroom, one bath mobile home on a quiet Florida island, with all the ...
From $149 per night (USD)Expedia
- From $250 per night (USD)
VRBO
My Sea Shack~ 1 minute to beach, SH Club access, golf cart
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Let "My Sea Shack" be your home away from home while you recharge your mind, body and soul on our island oasis, North Ca ...
From $250 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Gorgeous, Peaceful Island Retreat-3 Bedroom-2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It’s time for a Cool Change! Brand new rental available on Upper Captiva Island! Cool Change is a recently renovated, br ...
From $325 per night (USD)VRBO
- From $207 per night (USD)
VRBO
Beautiful waterfront 2-bed\/2-bath island getaway on Matlacha Island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Coqui Palace is a waterfront two bedroom, two bath island getaway in the Historic Matlacha Fishing Village. Fish fro ...
From $207 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Welcome to Blue Haven on beautiful North Captiva Island, Florida.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Blue Haven is located on North Captiva Island, Florida. No cars just a great place to relax and enjoy paradise!. The hou ...
From $325 per night (USD)Expedia
- Click For Pricing
Expedia
Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Better than Paradise...Bokeelia, FL. This quaint little fishing town located at the northend Pine Island, FL is perfect ...
Click For PricingExpedia
- From $168 per night (USD)
Expedia
Waterfront Matlacha Home w\/ Hot Tub & Grill!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Fall into a routine of sunbathing, boating, and enjoying the Florida gulf breeze from the comfort of this Matlacha Islan ...
From $168 per night (USD)Expedia
- From $855 per night (USD)
VRBO
Stella Maris-Beachfront, Privacy, Sunset Views all decks
- Bedrooms:
- 8
- Bathrooms:
- 3
- Sleeps:
- 6
Indulge in coastal paradise at our remarkable beachfront retreat. This exceptional 3-bedroom, 4-bathroom home is perfect ...
From $855 per night (USD)VRBO
- From $202 per night (USD)
Expedia
🔆🏝LITTLE PARADISE🏝🔆
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the ...
From $202 per night (USD)Expedia
- Click For Pricing
Expedia
Just Listed - Beautifully renovated waterfront 2 bedroom home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic 2 - bdrm 3 - bed waterfront (w doc) home ready for guests now. Perfect location on the north tip of Pine Isla ...
Click For PricingExpedia
- From $769 per night (USD)
Expedia
Flamingo Beach: Beach Front, Hot Tub and Endless Relaxation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 290 - Flamingo Beach house on North Captiva Island, where you can experience the best beach on the island fro ...
From $769 per night (USD)Expedia
- From $261 per night (USD)
VRBO
SeaSong - Words of the Ocean , Music of the Wind
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Single family home nestled near a quiet cul-de-sac , this 1000sq foot home creates a connection between the nearby sea a ...
From $261 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Paradise Found with Pool & 2 Boat lifts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous 3/2 offers a wonderful gulf access, split plan dressed in island style complete with pool, 2 boat lifts an ...
From $225 per night (USD)VRBO
- From $150 per night (USD)
VRBO
TURTLE COTTAGE AN ISLAND OASIS - PINE ISLAND
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"ISLAND VIBE" "Pine Island" Turtle Cottage is a totally remodeled, fully furnished and well appointed home located in th ...
From $150 per night (USD)VRBO
- From $163 per night (USD)
VRBO
Waterfront House, 2 Bdr, 2 bath, Boat Lift, Trailer Parking, and 2 Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
House upgraded in April 2023 on the water across from Sanibel Island at the end of Monroe Canal. Enjoy the awesome vie ...
From $163 per night (USD)VRBO
- From $255 per night (USD)
VRBO
NEW!! The “WATERSIDE” COTTAGE~With dockage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
World class tarpon fishing, superb flats fishing for reds, & Snook in the mangroves, Trout in the grass, giant Sharks in ...
From $255 per night (USD)VRBO
- From $232 per night (USD)
Expedia
Pine Island Beach House! *Gulf Access, Heated Pool, Hot Tub & Boat Dock*
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the "Blue Marlin"! St. James City on Pine Island is a fishing and boating community with old Florida charm! ...
From $232 per night (USD)Expedia
- From $103 per night (USD)
VRBO
Aaliyah`s and Amina`s Tropical Retreat - Pine Island St James City Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $103 per night (USD)VRBO
- From $109 per night (USD)
Expedia
Pine Island - Lina`s Tropical Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to what we call ... Lina's Tropical Retreat on beautiful St James City, Florida. We're located within Pine Islan ...
From $109 per night (USD)Expedia
- From $111 per night (USD)
VRBO
Aaliyah`s and Amina`s Tropical Retreat unit 2 - Pine Island St James City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $111 per night (USD)VRBO
- From $117 per night (USD)
Expedia
Aaliyah`s and Amina`s Tropical Retreat 4 - Pine Island St James City Florida
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $117 per night (USD)Expedia
- From $1250 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 $1250 per night (USD)VRBO
- From $359 per night (USD)
VRBO
SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Golf Cart-Sleeps 7
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
SMUGGLERS HIDEAWAY is a secluded 3 bedroom island home located on North Captiva Island. Nestled among palm trees, the h ...
From $359 per night (USD)VRBO
- From $109 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 $109 per night (USD)VRBO
- From $337 per night (USD)
Expedia
Stunning canal-front home with pools, AC, W\/D & hammock
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
Bocilla Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $337 per night (USD)Expedia
- From $99 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 $99 per night (USD)VRBO
- From $587 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 $587 per night (USD)Expedia
- From $161 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 $161 per night (USD)VRBO
- From $400 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 $400 per night (USD)Expedia
- From $305 per night (USD)
VRBO
Tarpon Penthouse Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Deluxe "Tarpon" Penthouse One bedroom apartment Living Room with Cable TV Kitchen with Refrigerator Bathroom with Bath & ...
From $305 per night (USD)VRBO
- From $81 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. Love boating? ...
From $81 per night (USD)Expedia
- From $186 per night (USD)
VRBO
3\/2 HEATED POOL HOME WITH BOAT LIFT! 3\/2 Waterfront, Pet Friendly Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This immaculate 3 bedroom, 2 bathroom home is waterfront with Direct Access to the Intra-coastal Waterway, your gateway ...
From $186 per night (USD)VRBO
- From $202 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 $202 per night (USD)Expedia
- From $216 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 $216 per night (USD)VRBO
- From $107 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 $107 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Welcome to Porchfish! 3\/2 in St. James City! Boat lift, Corner Lot, Beautiful Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to peace, welcome to paradise, welcome to PORCHFISH! This beautiful 3 bedroom, 2 bath home on Pine Island in St. ...
From $177 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Dream Screened Lanai & Pool 3+ months, Dream Screened Lanai
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a Home away from Home, in Sunny Florida. We are looking for you, if you want a 3+ month stay Jan-April 20 ...
From $295 per night (USD)Expedia
- From $642 per night (USD)
VRBO
Tropical Family Oasis: Green Tortuga
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
"Welcome to Green Tortuga: Your Tropical Oasis Awaits! Escape to Green Tortuga and experience the allure of the Caribbe ...
From $642 per night (USD)VRBO
- From $180 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 $180 per night (USD)VRBO
- From $340 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 $340 per night (USD)VRBO
- From $272 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 $272 per night (USD)Expedia
- From $1116 per night (USD)
VRBO
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 $1116 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Waterfront Matlacha Condo w\/ Patio + Pool Access!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience an 'Island Getaway' at this 2-bedroom, 2.5-bath end-unit condo in Matlacha! Nestled in a tropical landscape, ...
From $175 per night (USD)Expedia
- From $465 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 $465 per night (USD)VRBO
- From $657 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 $657 per night (USD)Expedia
- From $540 per night (USD)
VRBO
Blue Macaw: 3 Bedroom Home Just a Block From the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
079 - Blue Macaw is a beautiful 3 bedroom home located just a block away from the beach. The home boasts an upside-down ...
From $540 per night (USD)VRBO
- From $479 per night (USD)
Expedia
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 $479 per night (USD)Expedia
- From $547 per night (USD)
VRBO
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 $547 per night (USD)VRBO
- From $566 per night (USD)
Expedia
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 $566 per night (USD)Expedia
- From $986 per night (USD)
VRBO
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 $986 per night (USD)VRBO
- From $162 per night (USD)
Expedia
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 $162 per night (USD)Expedia
- From $199 per night (USD)
VRBO
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 $199 per night (USD)VRBO
- From $146 per night (USD)
Expedia
Bokeelia Cottage w\/ Private Pool & Tiki Bar!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Find a tropical paradise in your own backyard at this 2-bedroom, 2-bathroom Bokeelia vacation rental cottage! With all o ...
From $146 per night (USD)Expedia
- From $656 per night (USD)
VRBO
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 $656 per night (USD)VRBO
- From $958 per night (USD)
VRBO
The Green Flash: Gulf Front Home with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a tropical paradise with breathtaking views at Green Flash, a 4-bedroom Gulf front vacation home with a privat ...
From $958 per night (USD)VRBO
- From $676 per night (USD)
VRBO
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 $676 per night (USD)VRBO
- From $536 per night (USD)
Expedia
Coconut Castaway - Ocean Views, Walk to Beach, Golf Cart, Club Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
***Hurricane Update*** As of September 28, 2022 we are temporarily closed due to damages sustained from Hurricane Ian. W ...
From $536 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Coastal Bokeelia Oasis w\/ Pool, Deck & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hitch up your boat, gather the family, and embark on an unforgettable Florida adventure to this luxurious vacation renta ...
From $140 per night (USD)VRBO
- From $805 per night (USD)
Expedia
SPRAWLING PRIVATE BEACHFRONT - Sleeps 10, perfect for a family, 2 golf carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to SEA LA VIE beach house, your luxurious home away from home at the shore. Our private 4 bedroom beach house of ...
From $805 per night (USD)Expedia
- From $290 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 $290 per night (USD)VRBO
- From $179 per night (USD)
Expedia
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 $179 per night (USD)Expedia
- From $309 per night (USD)
VRBO
Bokeelia Island Oasis: Waterfront, Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $309 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Completely remodeled & prof design after hurricane! Open Jun 1! Lrg 5Bdr! Pool!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
*This property is located on North Captiva which is only accessible by ferry or boat. * North Captiva Island is a remot ...
From $1000 per night (USD)Expedia
- From $128 per night (USD)
VRBO
Fisherman's Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Here is an opportunity to rent one of the best waterfront units on Pine Island. The gorgeous views are across the water ...
From $128 per night (USD)VRBO
- From $244 per night (USD)
Expedia
Canalfront St James City Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Endless aquatic activities await at this St. James City vacation rental! This 3-bedroom, 2-bathroom home offers a Gulf C ...
From $244 per night (USD)Expedia
- From $99 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 $99 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Beautiful water-view home close to boat ramp, fishing and Gulf of Mexico.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to "Sealaxation House". Beautiful canal-side, two-story home. You'll feel like you're in a treehouse. Property ...
From $215 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Island Oasis- Olde Florida Keys atmosphere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Forget your worries in this spacious and serene space. Come & relax on this Olde Florida Vibe Island, there is so much ...
From $130 per night (USD)VRBO
- From $119 per night (USD)
Expedia
Island TreeTop House, Pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely cozy 2bed 1bath secluded house in quiet neighborhood. My home is very clean and uncluttered. Great for Two or t ...
From $119 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
BEAUTIFUL HOME! JUST OFF PINE ISLAND SOUND.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
No pets. Non smoking home. Smoking is prohibited ANYWHERE on property. This charming open plan home sleeps 4 and is a s ...
Click For PricingVRBO
- From $217 per night (USD)
VRBO
Private St James City Home w\/ Enclosed Deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $217 per night (USD)VRBO
- From $415 per night (USD)
Expedia
North Captiva Island- Ocean bay views and modern decor. Two new carts!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Bay - North Captiva Island Welcome to paradise! This townhome boasts the best of ocean bay views, wild beaches w ...
From $415 per night (USD)Expedia
- From $207 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 $207 per night (USD)VRBO
- Click For Pricing
Expedia
Relaxing Island View!
- 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 ...
Click For PricingExpedia
- From $825 per night (USD)
VRBO
NEW!!! THE BIRDS & THE BEACH - 4\/3 Sleeps 12, HUGE Private Pool, 2 GOLF CARTS\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
SPACIOUS 4 BR. 3 BATH - sleeps 12 in beds, 2 Golf Carts, PRIVATE HEATED POOL , SPECIAL PRICING FOR MAY BOOKINGS (Inquir ...
From $825 per night (USD)VRBO
- From $150 per night (USD)
Expedia
Sunset Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Matlacha, it’s a water sports paradise! World class fishing, boating, kayaking, beautiful sunrises and sunsets! See natu ...
From $150 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Newly Renovated Beach House! Book your Spring Break and \nSummer Vacations Now!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Relax and enjoy this unique piece of island paradise from our Spacious, custom designed, professionally decorated, luxur ...
From $550 per night (USD)VRBO
- From $295 per night (USD)
Expedia
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 $295 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Fun'n Sun - Charming 3 BR\/ 3 baths waterfront Villa w. boat lift
- 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 $250 per night (USD)VRBO
- From $1400 per night (USD)
Expedia
Captiva Beach Sunset ~Gulf front, pool, NCIC, 4 & 6 seater carts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Captiva Beach Sunset - 5 BR/4.5 BA - Sleeps 12 in beds- Beachfront with Private Pool Queen size air mattress is availabl ...
From $1400 per night (USD)Expedia
- From $119 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 $119 per night (USD)VRBO
- From $150 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 $150 per night (USD)Expedia
- Click For Pricing
VRBO
Private Pool Home Spectacular Sunsets Steps from the Beaches & StarLink Internet
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Your search for the PERFECT beach vacation house is over with your search for "Captiva Isles on North Captiva Island, FL ...
Click For PricingVRBO
- From $219 per night (USD)
VRBO
Quick Gulf Access. This Home has it all.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This home has it all: Direct Five Minute Access, Boat Dock with Use Of Lift Optional. Quiet Neighborhood, Restaurants an ...
From $219 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Fisherman & Kayaker's Delight! 3 BR, 2 BA Waterfront Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This inviting 3-bedroom, 2-bathroom stilt home (stairs required to entrance) is an idyllic retreat for your Southwest Fl ...
From $286 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Bocilla Island Club Condo, Boat Dock, 400 foot Private Pier, 2 Pools, Tennis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
16709 Bocilla Palms Dr., Bokeelia Our condo also includes a private dock capable of holding a boat up to 36ft, 400 foot ...
From $119 per night (USD)VRBO
- From $239 per night (USD)
VRBO
LUXE TOWNHME CLUB w\/POOL! 4 BRs, 2 KINGS, KAYAKS & GOLF CART INC, DOCKAGE AVAIL!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
*** The FABULOUS “DRAGONFLY POINT” is a LUXURY ISLAND TOWNHOME located on North Captiva Island! A Remote Barrier Island ...
From $239 per night (USD)VRBO
- From $225 per night (USD)
VRBO
3 bed, 3 bath home, heated\/cooled pool on quiet canal. Quick boat access to gulf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Treehouse is a well appointed comfortable three bedroom three bathroom home, with a heated pool, situated on a tranquil ...
From $225 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Oceanfront beach home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Robin’s Beach Nest is located on some of the most prized beachfront property on the entire island, featuring some of the ...
From $600 per night (USD)VRBO
- From $367 per night (USD)
VRBO
Calling Waters-Gulf access w\/dock, pool and HT.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This canal front home has a heated pool, private dock capable of hosting a 25-foot boat, barbecue grill, patio space, sc ...
From $367 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Paradise at Serenity Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled away in a quiet community on Pine Island’s NE side, this home is an angler’s or kayaker’s paradise! The home is ...
From $150 per night (USD)VRBO
- From $160 per night (USD)
VRBO
\"The Mermaid\" - Living in a Lush Tropical Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Vacation Rental: Newly renovated cottage on Pine Island near Fort Myers, Florida. #YesVrbo Perfect couple's getaway. ...
From $160 per night (USD)VRBO
- From $467 per night (USD)
VRBO
GORGEOUS BEACH HOUSE 4 BRS, PRIVATE POOL, 360 H2O Views 2 Carts, Outdoor Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
FANTASTIC OPPORTUNITY! BEAUTIFUL HOME! GREAT RATES! BOOK NOW! Thank you for your interest in Paloma Beach House! Book u ...
From $467 per night (USD)VRBO
- From $75 per night (USD)
VRBO
Spacious Getaway, 1 to 4 for Easy Going Nature Lovers on beautiful Pine Island.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Comfy home w pretty garden on historic Pine Island. Nearby fishing, kayaking, birding, good eats, tennis. Visit pristine ...
From $75 per night (USD)VRBO
- From $808 per night (USD)
VRBO
Heated pool, private beach, Boat Bar! Large Island home 100 steps to the water!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Recently updated, 5 Star Property! We are located on the northern tip of North Captiva Island, with lots of privacy away ...
From $808 per night (USD)VRBO
- From $1259 per night (USD)
VRBO
Parrothead's Paradise - 4 BR House - Private Boat Dock & Brand New Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Parrothead's Paradise! Located on the secluded barrier island of Upper Captiva, Parrothead’s Paradise is a l ...
From $1259 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Soak up Paradise as you Relax in Pool\/Spa Home surrounded by Happy Wildlife
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
New in 2021 Heated Salt Water Pool and Spa on Marble Lanai, with screened enclosure. This side-by-side home is 7 years y ...
From $185 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Beautiful \"Old Florida\" Pine Island Golf Course & Marina Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a lovely, updated 4/3 stilt home located directly on the Alden Pines Golf Course and only 1/2 block from the Pin ...
From $175 per night (USD)VRBO