Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $259 per night (USD)VRBO
Unique Charlotte Harbor experience on a comfortable Schucker 436 trawler.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boaters Only at this time. I want to welcome boaters to an experience of a lifetime! You must have a boat that you can ...
From $259 per night (USD)VRBO
From $409 per night (USD)VRBO
The Bokeelia Boathouse, waterfront, Boat Dock, Pine Island, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise awaits you at our recently renovated island get away home. Located on the water in Bokeelia on Pine Island we ...
From $409 per night (USD)VRBO
From $626 per night (USD)VRBO
Beach's Edge, On the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home is right on the Florida sugar sand beach, which is often uninhabited except by wading birds, ghost c ...
From $626 per night (USD)VRBO
From $628 per night (USD)VRBO
Perfect Placement, A beautiful beachfront home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home (sleeps 6 adults and 4 children) is extremely close to the ocean and a Florida sugar sand beach whic ...
From $628 per night (USD)VRBO
From $951 per night (USD)VRBO
New luxury pool home, 2 min to beach, 360 water views, club available
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 19
Overview of the property: • Sublime is a brand new, stunning 3,200 square foot, 7-bedroom, 6-bathroom, luxury beach hom ...
From $951 per night (USD)VRBO
From $566 per night (USD)Expedia
The Pearl Beach House, North Captiva Island, FL | Enhanced cleaning measures
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This water-front property offers designer furniture and panoramic views throughout. Experience unprecedented privacy wit ...
From $566 per night (USD)Expedia
From $169 per night (USD)VRBO
Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are looking to get away from it all and surround yourself in Florida's tropical nature then Pine Island is the pl ...
From $169 per night (USD)VRBO
From $572 per night (USD)VRBO
STEPS TO THE BEACH - Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
* ISLAND ACCESSED BY FERRY ONLY LANIKAI is a 2 bedroom, 2 bath house only steps from the beach, with a private heated p ...
From $572 per night (USD)VRBO
From $370 per night (USD)VRBO
SEASIDE VILLA DESTIN - In the heart of Pine island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our SEASIDE VILLA DESTIN is idyllically located on Pine Island, which is situated in front of Cape Coral. Especially for ...
From $370 per night (USD)VRBO
From $188 per night (USD)Expedia
Gulf Coast Hidden Jewel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Time! Gulf access waterfront oasis. Two bedrooms, 1 full bath, full size kitchen and washer/dryer. Sle ...
From $188 per night (USD)Expedia
From $358 per night (USD)VRBO
Island Time Tropical Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Island Time! Gulf access waterfront home. Great for family or groups sharing. 3 bedrooms, 2 full baths, 2 ful ...
From $358 per night (USD)VRBO
From $126 per night (USD)Expedia
Sunrise In Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Island Time! Gulf access waterfront oasis. 1 bedroom, 1 full bath with bath tub, 1 kitchen, washer/dryer. Acc ...
From $126 per night (USD)Expedia
From $745 per night (USD)VRBO
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Incredible newly renovated 3 bedroom home with gulf views! Open layout with exceptional outdoor spaces including huge fr ...
From $745 per night (USD)VRBO
From $379 per night (USD)VRBO
Florida Island Paradise Home, Bokeelia Canal, Pine Island, w\/Pool & Boat Lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Time Inn! This 3 BR, 3 bath private home is located in Bokeelia Isles, Pine Island, Florida. Welcome ...
From $379 per night (USD)VRBO
From $1760 per night (USD)VRBO
Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Stunning sunset views and superior craftsmanship combine with casual elegance in this reverse floor plan beach home, des ...
From $1760 per night (USD)VRBO
From $339 per night (USD)VRBO
Island Getaway Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3Bedroom 2 bath remodeled pool home in St James City Triple lot with plenty of privacy with huge 13' deep pool with a wa ...
From $339 per night (USD)VRBO
From $760 per night (USD)VRBO
LVCC Villa Green Adventure
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This spectacular Vacation Villa will take you on a green adventure, in more than one way. Firstly, when thinking of the ...
From $760 per night (USD)VRBO
From $388 per night (USD)VRBO
House on Matlacha Pass with pool, hot tub, kayak dock & 12k lb boat lift!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our spacious open concept home with a great outdoor living space that opens up fully to a lanai overlooking the Ma ...
From $388 per night (USD)VRBO
From $803 per night (USD)VRBO
Waterfront Property with Dock and 2 Minute Walk to the Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful, brand new, resort style, four bedroom home just completed in October, 2020 and located right on Rum Road; wal ...
From $803 per night (USD)VRBO
From $841 per night (USD)VRBO
Beachy Keen, newly constructed pool home near beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
A stay in Paradise! Beautifully appointed, newly built home on your own secluded Upper Captiva island. 3 bedroom 2.5 b ...
From $841 per night (USD)VRBO
From $130 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 $130 per night (USD)VRBO
From $1478 per night (USD)Expedia
BEACHFRONT, HEATED POOL, KAYAKS\/SUP, LANAI W\/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
* ALWAYS CLEANED AND SANITIZED BY A PROFESSIONAL CLEANING SERVICE!! Welcome to North Captiva Island, a private, bridge-l ...
From $1478 per night (USD)Expedia
From $184 per night (USD)VRBO
Comfortable and relaxing house located on a deep water canal.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Cute little house located on a deep water canal in the heart of Matlacha. The primary bedroom has a king-sized bed and t ...
From $184 per night (USD)VRBO
From $286 per night (USD)VRBO
Peacock Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Awesome Matlacha Beauty- Vacation Rental, perfect for snowbirds & your little furry friend too!! Enjoy the warm Florida ...
From $286 per night (USD)VRBO
From $382 per night (USD)VRBO
☀️TRANQUILITY VILLA☀️
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $382 per night (USD)VRBO
From $360 per night (USD)VRBO
Come spend some island time at Reel Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Reel Paradise is a two bedroom two bathroom house on a fenced in large lot located in Matlacha, Florida. The inside is f ...
From $360 per night (USD)VRBO
From $979 per night (USD)VRBO
Sanderella- Ocean Front Vacation Home w\/ Large Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Sanderella, North Captiva's most family-fun oriented rental with the best unobstructed views of the water and ...
From $979 per night (USD)VRBO
From $91 per night (USD)VRBO
Saint James City- Southwest Fl little paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated 2 Bedroom, 2 bathroom with direct access. King bed in master bedroom with walk in closet. Twin beds in g ...
From $91 per night (USD)VRBO
From $506 per night (USD)VRBO
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This charming home is in the perfect location on North Captiva Island. The private heated pool and hot tub won’t stop yo ...
From $506 per night (USD)VRBO
From $393 per night (USD)VRBO
North Captiva Island Beach House\/60 Second Walk to 4 Miles of Awesome Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
***** GOLF CART AVAILABLE WITH RENTAL***** Winterhaven 4550 Oyster Shell Drive North Captiva Island, Florida NORTH CAPTI ...
From $393 per night (USD)VRBO
From $761 per night (USD)VRBO
Endless Summer - In Search of the Perfect House in North Captiva, sleeps 10.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the Endless Summer for your next vacation getaway. Endless Summer is a 3 bedroom 2.5 bath home with a heated pool ...
From $761 per night (USD)VRBO
From $144 per night (USD)VRBO
Spacious apartment located within the heart of paradise.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A two-bedroom, two-bathroom, 2nd-floor apartment, located in a duplex on a dead-end road in the heart of Pine Island Cen ...
From $144 per night (USD)VRBO
From $438 per night (USD)VRBO
2B\/2B Private Heated Pool, Games, Golf Cart, Club Access, Updated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Thank you for your interest in Magic Po'Cean and North Captiva Island. Leave your car (and your cares) at Pineland Mari ...
From $438 per night (USD)VRBO
From $145 per night (USD)VRBO
Cozy Tropical Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy 2 bedroom /1 bath retreat - located on a quiet residential street. Within walking distance to boat ramp, kayak ren ...
From $145 per night (USD)VRBO
From $488 per night (USD)VRBO
\"PERFECT SHELL\"LUXURY HOUSE STEPS 2 OCEAN*LRG POOL*FRONT BALCONY*AMENITY PACKED!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***Great Rates, Heated Pool Home, with an Excellent Island Location - High and Dry area which matters! And only Steps t ...
From $488 per night (USD)VRBO
From $1272 per night (USD)VRBO
Peace of Paradise: Pvt., swing bar, pool, beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
(In recent news...The fall of 2024 was a challenging one for North Captiva Island due to hurricanes passing through. Pe ...
From $1272 per night (USD)VRBO
From $1226 per night (USD)VRBO
Special summer pricing! Luxury Beach House, Private Pool, just steps to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Do not miss the opportunity to enjoy a relaxing family friendly summer getaway at one of North Captiva's best properties ...
From $1226 per night (USD)VRBO
From $155 per night (USD)Expedia
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $155 per night (USD)Expedia
From $403 per night (USD)VRBO
Spectacular Nature! Waterfront! Prime Tarpon Fishing! Bring Boat, 2 Free Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Taking reservations for 2024 & 2025. No hurricane damage. Fishing enthusiasts, kayakers, bird watchers, nature lovers... ...
From $403 per night (USD)VRBO
From $1285 per night (USD)Expedia
At the Beach: Heated Pool, Golf Cart, Club Access, Winter Dates Avail! Book Now
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Gulf Swells & Sea Shells – your ultimate oceanfront haven! Completely renovated, this stunning 5-bedroom, 5-b ...
From $1285 per night (USD)Expedia
From $481 per night (USD)VRBO
Rockstar Beach House North Captiva Island 25’ private boat dock NCIC pools Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** UPDATE ** Rockstar has many recent upgrades including a new Reverse osmosis system in the kitchen, added Super fast S ...
From $481 per night (USD)VRBO
From $885 per night (USD)VRBO
BEACH FRONT with the best sunsets on the island!!!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Newly remodeled, ON THE BEACH! OCEAN FRONT HOME ON PRISTINE SANDY WHITE BEACHES Spectacular views, best sunsets! WE ar ...
From $885 per night (USD)VRBO
From $1597 per night (USD)VRBO
Steps from the beach, gulf views, on the airstrip and Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you are searching for an island vacation that is different from all others, then search no more for you have stumbled ...
From $1597 per night (USD)VRBO
From $534 per night (USD)VRBO
Island Oasis\/Hidden Beach House-Private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This traditional, Florida-style island cottage is situated less than 200 yards down a private path to the Gulf of Mexic ...
From $534 per night (USD)VRBO
From $522 per night (USD)VRBO
Newly Renovated Island Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise, no cars, no crowds. Located in the Castaway Key subdivision on the island, this charming cottage ha ...
From $522 per night (USD)VRBO
From $447 per night (USD)VRBO
Southwest Florida Home Pool Fishing Biking Hiking Sun & Fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty and charm of Pine Island, Florida, with our spacious three-bedroom vacation rental, complete with a ...
From $447 per night (USD)VRBO
From $484 per night (USD)VRBO
LaySea 8 - Across from Nature Preserve and steps to the best beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LaySea 8 is an octagonal house with a spectacular 360 degree view of the Gulf of Mexico, Nature Preserve and Pine Island ...
From $484 per night (USD)VRBO
From $280 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 $280 per night (USD)VRBO
From $155 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $155 per night (USD)VRBO
From $153 per night (USD)VRBO
Private Hideaway in Pine Island community Pool and Marina a few steps away.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is my personal dream getaway I’m newly sharing with avid travelers looking to escape their hectic lives and live in ...
From $153 per night (USD)VRBO
From $688 per night (USD)VRBO
Prime Spot on Pristine North Captiva Island. Private Elevated Pool & Deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to North Captiva Island! A short, ferry ride separates you from reality, for your tropical paradise vacation. A ...
From $688 per night (USD)VRBO
From $338 per night (USD)VRBO
LUXURY ISLAND TOWNHME\/CLUB w\/POOL! 4 BRs, 2 KINGS, KAYAKS, & BOAT 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 $338 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
From $229 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 $229 per night (USD)VRBO
From $450 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 $450 per night (USD)VRBO
From $197 per night (USD)Expedia
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 $197 per night (USD)Expedia
From $701 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 $701 per night (USD)VRBO
From $80 per night (USD)VRBO
Spacious Getaway, 1 to 4 for Easy Going Nature Lovers on beautiful Pine Island.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Comfy home w pretty garden on historic Pine Island. Nearby fishing, kayaking, birding, good eats, tennis. Visit pristine ...
From $80 per night (USD)VRBO
From $1139 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 $1139 per night (USD)VRBO
From $243 per night (USD)VRBO
Soak up Paradise and Relax in Heated 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 $243 per night (USD)VRBO
From $219 per night (USD)VRBO
Beautiful \"Old Florida\" Pine Island Golf Course & Marina Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $219 per night (USD)VRBO
From $538 per night (USD)Expedia
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
***Post Hurricane Ian Update 6/1/23*** Thank you for your interest in Tarpon Cove. We’re happy to report that the isla ...
From $538 per night (USD)Expedia
From $399 per night (USD)VRBO
SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
‼️ASK ABOUT LAST-MINUTE BOOKING SPECIALS‼️ TRUE ISLAND EXPERIENCE: Steps from the water and right next to the bay, The ...
From $399 per night (USD)VRBO
From $274 per night (USD)Expedia
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 $274 per night (USD)Expedia
From $267 per night (USD)VRBO
Skipper Lane on Salt Water Canal, Easy Gulf access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated, Open Concept 2 Bed 2 Bath Gulf Access Home in the Heart of St. James City. Fisherman’s Dream Awaits!! Two Man ...
From $267 per night (USD)VRBO
From $396 per night (USD)VRBO
North Captiva Point House - Boat\/Water Taxi Only **NEWLY RENOVATED **
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
****This property can only be accessed by boat or water taxi.**** The North Captiva Point House was built by Barnacle ...
From $396 per night (USD)VRBO
From $129 per night (USD)VRBO
Serenity Bay #2 Street-side
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This is a studio apartment, with a queen bed, kitchen with two burner cook top, microwave, toaster, coffee pot, and 4 cu ...
From $129 per night (USD)VRBO
From $401 per night (USD)VRBO
LUXURY ISLAND RENTAL\/CLUB w\/POOL, KAYAKS, 4BR PRIV BEACH ACCESS, BOAT DOCK AVAIL
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
FANTASTIC NEW LUXURY ISLAND RENTAL! OPEN and WELCOMING GUESTS! ONE 4 PERSON GOLF CART INCLUDED COMPLIMENTARY IN YOUR VAC ...
From $401 per night (USD)VRBO
From $146 per night (USD)VRBO
Serenity Bay Studio #3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In addition to the Big House on our property, we have a 4-plex, with four studio apartments. Two face the water, two fa ...
From $146 per night (USD)VRBO
From $283 per night (USD)VRBO
My Only Sunshine Island Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our beautifully remodeled 2-bedroom, 2-bath POOL HOME nestled on a canal leading to Matlacha Pass in the pict ...
From $283 per night (USD)VRBO
From $153 per night (USD)VRBO
*** Studio Tarpon located directly on the Gulf of Mexico ***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Tarpon Suite" in a house with 4 apartments by the water - Cute studio for max. 3 persons - living area with slee ...
From $153 per night (USD)VRBO
From $1280 per night (USD)Expedia
Serendipity is BACK - Complete remodel April 2024 - Pool; 2 Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Serendipity beach house is Back and is Better than ever with a COMPLETE REMODEL finished April 2024. Located one hu ...
From $1280 per night (USD)Expedia
From $270 per night (USD)VRBO
Prettiest Sunset View Pine Island, Waterfront Home on Water
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome This is the fishermans delight. In addition to staying in the hous ...
From $270 per night (USD)VRBO
From $313 per night (USD)Expedia
Remodeled 3\/2 on quiet canal with 10k boatlift, 5 mins to Charlotte Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Up and running after hurricane Ian and accepting seasonal rentals! the property has a new metal roof and seawall and wor ...
From $313 per night (USD)Expedia
From $267 per night (USD)VRBO
Paradise just waiting for you!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you are looking for an awesome get-a-way, we have the place for you! If you love to fish, swim or just enjoy the Flo ...
From $267 per night (USD)VRBO
From $572 per night (USD)VRBO
Great Island Retreat- Walk to Beach and Pools
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
PLEASE CONTACT US ABOUT DISCOUNTS FOR RENTALS GREATER THAN 14 DAYS. ALSO FOR STAYS OF 4 DAYS MAXIMUM GUEST COUNT IS 6 ...
From $572 per night (USD)VRBO
From $183 per night (USD)VRBO
Cottage with private deck in the heart of Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a small cottage with an attached in-law unit, that has the option to rent the house as a 2-bed bath due to this ...
From $183 per night (USD)VRBO
From $233 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Reel Suite". Compared t ...
From $233 per night (USD)VRBO
From $1200 per night (USD)VRBO
Bluefin Beach House, Luxury Home with Pool & Spa on North Captiva, 2 Golf Carts
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Bluefin Beach House is a professionally designed and decorated beach home located just 300 feet from the Gulf of Mexico ...
From $1200 per night (USD)VRBO
From $247 per night (USD)VRBO
Fisherman's Paradise on the Canal with Covered Boat Lift and Dock\/ Gulf Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please come and enjoy our beautiful 3 BR/2BA 1865 Sq ft home located in the quaint fishing village of Matlacha. Matlach ...
From $247 per night (USD)VRBO
From $117 per night (USD)VRBO
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore Pine Island and the Florida Gulf Coast from this retro two-room cottage set in a pretty back yard. 45 min from F ...
From $117 per night (USD)VRBO
From $166 per night (USD)VRBO
Pine Island Retreat 2\/2 on Canal!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Pine Island treasure is conveniently located in Flamingo Bay. 2 bedroom 2 bathroom. Each room has it's own full bat ...
From $166 per night (USD)VRBO
From $234 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Lure Suite". Compared t ...
From $234 per night (USD)VRBO
From $853 per night (USD)VRBO
All Conched Out - Luxe 3 Br, Private pool, outdoor pool table - pets considered
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
All Conched Out This adorable “pink palace” retreat has everything you need for a fun, wonderful and relaxing vacation ...
From $853 per night (USD)VRBO
From $147 per night (USD)VRBO
Gorgeous canal front home located on Pine Island w\/boat lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This premier waterfront home located on a deep water canal with 80 feet of sea wall with direct access to the Intracoast ...
From $147 per night (USD)VRBO
From $217 per night (USD)VRBO
Kinsey's Beach Shack- Perfect getaway for two!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The North Captiva Fish Camp is located on the peninsula of the island nestled between Safety Harbor and Pine Island Soun ...
From $217 per night (USD)VRBO
From $1439 per night (USD)VRBO
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 18
Overview of the property: • No Worries Atoll is a stunning 3,300 square foot pool home that is currently being complete ...
From $1439 per night (USD)VRBO
From $312 per night (USD)VRBO
ISLAND LIVING, BOATER'S PARADISE, AND MODERN LUXERY !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
If you want it all in a vacation home, this Gulf access waterfront home is the gem you have been looking for. Do you ne ...
From $312 per night (USD)VRBO
From $173 per night (USD)VRBO
Waterfront Home - Cherry Properties Pine Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a beautiful fully furnished 2004 Manufactured Home. The home was remodeled and updated in Fall of 2021. In addit ...
From $173 per night (USD)VRBO
From $646 per night (USD)VRBO
World Class Fishing, direct canal on Gulf of Mexico, 3\/3, boat lift, heated pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Luxury waterfront home with heated pool, direct Gulf access with private docking for your boat. Open concept layout with ...
From $646 per night (USD)VRBO
From $940 per night (USD)VRBO
Escape To Paradise - Breathtaking Views- Pool-Steps to the beach - 2 Golf Carts!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Escape To Paradise Beach House , a spectacular 4 bedroom, 4 bathroom home that sleeps 10- Completely remo ...
From $940 per night (USD)VRBO
From $184 per night (USD)VRBO
Fishermen, Kayakers & Birdwatchers Paradise -Fish in 5 Minutes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 3
Location: Bokeelia, Pine Island, Florida South West Florida, USA (25 miles to Fort Myers International Airport) A fishe ...
From $184 per night (USD)VRBO
From $275 per night (USD)VRBO
Hurricane Ian update Roofs are on pools are heated life rolls on Thank God
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Beautifully upgraded yet very comfortable condo it the best fishing spot! Over looking the pool and watet inlet. Enjoy t ...
From $275 per night (USD)VRBO
From $160 per night (USD)VRBO
Serenity Bay Studio 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
On the same property as Serenity Bay Cottages, Big House, is a 4 plex, with four studio apartments. Each about 250 sq. ...
From $160 per night (USD)VRBO
From $1380 per night (USD)VRBO
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Since 2017, "The Blue Marlin" has provided sea-loving families with the ultimate North Captiva beachfront retreat. This ...
From $1380 per night (USD)VRBO
From $956 per night (USD)Expedia
Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Newly remodeled Luxury 4 BR/5 BA - Brand New Kitchen and Baths – Close to beach, Island Club and Preserve, yet a privat ...
From $956 per night (USD)Expedia
From $114 per night (USD)VRBO
St. James City; Pine Island Cove- 55 yrs and older Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Private home located on the canal-2 bedrooms/2 bathrooms in a 55 yr and older community. Only 2 guests full time and on ...
From $114 per night (USD)VRBO
From $897 per night (USD)VRBO
AWESOME HUGE BEACH HOUZ GREAT FLOOR PLAN VIEWS PRIVATE POOL CLUB!2 CARTS PETS
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
RUFF LIFE is a WOW Beach Vacation Rental! Tropical Ruff Life Beach House is Amenity Packed! It is a Truly Fantastic, L ...
From $897 per night (USD)VRBO
From $360 per night (USD)VRBO
Canal Life On Matlacha!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Canal life says it all as you relax in this unique spacious home on the quaint little island of Matlacha. Sleeps 8 easil ...
From $360 per night (USD)VRBO
From $886 per night (USD)VRBO
BEAUTIFUL OCEANFRONT BEACH LOCATION - View dolphins & Manatees from Living Room!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
This oceanfront 6 bedroom home is located on North Captiva Island and can accommodate up to 18 people. It comes with th ...
From $886 per night (USD)VRBO