Calusa Land Trust and Nature Preserve of Pine Island Rentals
- Click For Pricing
VRBO
Looking for a soothing and peaceful place to rest and enjoy paradise?
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our condo is newly furnished, fresh and clean all around, enjoy looking at boats cruising by the canal, great restaurant ...
Click For PricingVRBO
- Click For Pricing
VRBO
Canal Front Home , direct Gulf access with lanai and dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and enjoy your 2/2 home. Perfect secluded waterfront location.with your private dock, You are minutes away Sanibe ...
Click For PricingVRBO
- From $250 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 $250 per night (USD)VRBO
- From $220 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 $220 per night (USD)VRBO
- From $138 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 $138 per night (USD)VRBO
- From $262 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 $262 per night (USD)VRBO
- From $103 per night (USD)
VRBO
BEST FISHING AREA \/ Reopened in November 2023
- 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 $103 per night (USD)VRBO
- From $420 per night (USD)
VRBO
Luxury Home on Private Island with Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have you ever dreamed of taking a vacation to a Semi Private Island? Do you want to experience Paradise without leaving ...
From $420 per night (USD)VRBO
- From $273 per night (USD)
VRBO
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 $273 per night (USD)VRBO
- From $225 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 $225 per night (USD)VRBO
- From $1300 per night (USD)
VRBO
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 $1300 per night (USD)VRBO
- From $675 per night (USD)
VRBO
All Conched Out - Luxe 3 Br, Private pool, outdoor pool table - pets considered
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
All Conched Out This adorable “pink palace” retreat has everything you need for a fun, wonderful and relaxing vacation ...
From $675 per night (USD)VRBO
- From $315 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 $315 per night (USD)VRBO
- From $449 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 $449 per night (USD)VRBO
- From $157 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 $157 per night (USD)VRBO
- From $184 per night (USD)
VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $184 per night (USD)VRBO
- From $745 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 $745 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $78 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 $78 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Pine Island Retreat 2\/2 on Canal with boat lift!!
- 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 $125 per night (USD)VRBO
- From $185 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 $185 per night (USD)VRBO
- From $120 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 $120 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Welcome to Crab Cakes cottage on beautiful North Captiva Island, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great location on the island. Close to beaches and in a quiet area. House has a large deck with patio furniture and gas ...
From $400 per night (USD)VRBO
- From $151 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 $151 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Wow stunning and world class fishing w boat lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Luxury waterfront home with heated pool, direct Gulf access with private docking for your boat. Open concept layout with ...
From $499 per night (USD)VRBO
- From $750 per night (USD)
Expedia
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 $750 per night (USD)Expedia
- From $279 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 $279 per night (USD)VRBO
- From $1050 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 $1050 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $842 per night (USD)
VRBO
Ultimate luxury resort style home on Matlacha
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This is a single family home in highly desirable Matlacha. Matlacha features fun art galleries, dining and boating. Th ...
From $842 per night (USD)VRBO
- From $150 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 $150 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Hurricane Ian update Roofs are on pools are heated life rolls on Thank God
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Beautifully upgraded yet very comfortable condo it the best fishing spot! Over looking the pool and watet inlet. Enjoy t ...
From $225 per night (USD)VRBO
- From $130 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 $130 per night (USD)VRBO
- From $1195 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 $1195 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Great Reviews - Lake view - Peaceful location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This is a beautiful and traditional Florida stilt home, with elevated view for your ideal vacation on undeveloped Pine ...
From $250 per night (USD)VRBO
- From $900 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 $900 per night (USD)Expedia
- From $99 per night (USD)
VRBO
St. James City; Pine Island Cove- 55 yrs and older Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $99 per night (USD)VRBO
- From $711 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 $711 per night (USD)VRBO
- From $576 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 $576 per night (USD)VRBO
- From $1457 per night (USD)
VRBO
Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Stunning views of sunset and superior craftsmanship combine with casual elegance in this reverse floor plan beach home, ...
From $1457 per night (USD)VRBO
- From $660 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 $660 per night (USD)VRBO
- From $268 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 $268 per night (USD)VRBO
- From $330 per night (USD)
VRBO
House on Matlacha Pass with pool, hot tub, kayak dock & 10k 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 $330 per night (USD)VRBO
- From $650 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 $650 per night (USD)VRBO
- From $750 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 $750 per night (USD)VRBO
- 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 $1200 per night (USD)
VRBO
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 $1200 per night (USD)VRBO
- From $118 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 $118 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Welcome to paradise! You're now on island time!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to island paradise! Jimmy Buffet meets Pottery Barn! A beautiful slice of amazing on the water. Enjoy the unspoi ...
From $350 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Manatee House Tropical Retreat *ONLY BOOKING FOR CONTRACTORS AT THIS TIME*
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our Ultimate Vacation Getaway in a quiet friendly neighborhood located on a wide direct Gulf Access canal. En ...
From $385 per night (USD)VRBO
- From $242 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 $242 per night (USD)VRBO
- From $236 per night (USD)
VRBO
☀️TRANQUILITY VILLA☀️
- Bedrooms:
- 3
- 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 $236 per night (USD)VRBO
- From $256 per night (USD)
VRBO
Come spend some island time at Reel Paradise
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $256 per night (USD)VRBO
- From $96 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 $96 per night (USD)Expedia
- Click For Pricing
Expedia
Ocean Boulevard-New Steps To The Beach - Professionally Decorated -2 Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Breathtaking elegance awaits you at the Ocean Boulevard located approximately 400 feet from the gulf. This brand new (s ...
Click For PricingExpedia
- From $599 per night (USD)
VRBO
May, Last min SPECIAL 599 ON THE WATER! Best beach & Sunsets on island! 5 Stars!
- 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 $599 per night (USD)VRBO
- From $313 per night (USD)
VRBO
Spectacular Nature! Waterfront! Prime Tarpon Fishing! Bring Boat, 2 Free Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tired of the cold? Need a warm & tropical place to stay? Let’s Go! Fishing enthusiasts, kayakers, bird watchers, nature ...
From $313 per night (USD)VRBO
- From $1018 per night (USD)
Expedia
Exclusive At the Beach: Pvt Pool, Golf Cart, Club Access, FL Sunshine! 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 $1018 per night (USD)Expedia
- From $397 per night (USD)
VRBO
Rockstar Beach House North Captiva Island …accessible by ferry boat only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
** UPDATE ** Rockstar has many recent upgrades including a new Reverse osmosis system in the kitchen, added Super fast S ...
From $397 per night (USD)VRBO
- From $831 per night (USD)
VRBO
Steps from the beach, gulf views, on the airstrip and Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
If you are searching for an island vacation that is different from all others, then search no more for you have stumbled ...
From $831 per night (USD)VRBO
- From $521 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 $521 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- From $390 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 $390 per night (USD)VRBO
- From $411 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 $411 per night (USD)VRBO
- Click For Pricing
VRBO
Moonshine Acres Tropical Horse Farm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Moonshine Acres is located in the historic Saint James section of Pine Island. Our home is conveniently located near num ...
Click For PricingVRBO
- From $96 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 $96 per night (USD)VRBO
- From $110 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 $110 per night (USD)VRBO
- From $563 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 $563 per night (USD)VRBO
- Click For Pricing
VRBO
Pool Home, Steps from the Beach and Spectacular Sunsets plus StarLink Internet
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Your search for the PERFECT beach vacation house is over with your search for "Havana Breeze on North Captiva Island, FL ...
Click For PricingVRBO
- From $135 per night (USD)
VRBO
Pine Island Condo in beautiful Bokeelia, Florida 2 bed, 2 1\/2 bath, w\/boat dock
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Stay at Bocilla Island Club and enjoy this beautiful 2 bedroom, 2 1/2 bath condo featuring a king size bed and a queen ...
From $135 per night (USD)VRBO
- 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 $529 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 $529 per night (USD)VRBO
- From $339 per night (USD)
VRBO
North Captiva Island Beach House\/60 Second Walk to 4 Miles of Awesome Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***** GOLF CART AVAILABLE WITH RENTAL***** Winterhaven 4550 Oyster Shell Drive North Captiva Island, Florida NORTH CAPTI ...
From $339 per night (USD)VRBO
- From $463 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 $463 per night (USD)VRBO
- From $124 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 $124 per night (USD)VRBO
- From $375 per night (USD)
VRBO
2B\/2B Private Heated Pool Golf Cart ICNC Access New Landscaping & Games Modern
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $375 per night (USD)VRBO
- From $101 per night (USD)
VRBO
Cozy Tropical Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy 2 bedroom /1 bath home on a quiet residential street - less than a block to public boat ramp. The ramp is Lavender ...
From $101 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- From $75 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 $75 per night (USD)VRBO
- From $906 per night (USD)
VRBO
Peace of Paradise - Private Pool & 2 Golf Carts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
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 $906 per night (USD)VRBO
- From $356 per night (USD)
VRBO
\"PERFECT SHELL\"LUXURY HOUSE STEPS 2 OCEAN*LRG POOL*FRONT BALCONY*AMENITY PACKED!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***Current Openings for 2024 are 5/17-5/25, 7/6- 7/13, 7/20-7/27, 8/24-8/31 and on! Great Rates, Private Pool Home, wit ...
From $356 per night (USD)VRBO
- From $1193 per night (USD)
VRBO
Luxury Beach House, Completely Remodeled. Special pricing for Summer!!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
HIGH SPEED INTERNET - We now have Starlink satellite high speed internet, providing speed of up to 400 MBS, so work from ...
From $1193 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Tropical Point\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the whole family at this peaceful place to stay. Away from the noise of the city. Bring your kayak! Just one ...
From $120 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Cozy Matlacha Bungalow newly renovated is an easy stroll to shopping and dining.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Manatee is a wonderfully charming freshly remodled cottage, easy walking distance to fun shopping and restaurants. ...
From $100 per night (USD)VRBO
- From $273 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 $273 per night (USD)VRBO
- From $1085 per night (USD)
VRBO
BEAUTIFUL OCEANFRONT BEACH LOCATION - JANUARY 2024 DISCOUNTS!!!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
This oceanfront 6 bedroom home can accommodate up to 18 people. It comes with the North Captiva Island Club membership ...
From $1085 per night (USD)VRBO
- From $220 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 $220 per night (USD)VRBO
- From $266 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 $266 per night (USD)VRBO
- From $580 per night (USD)
VRBO
Beach's Edge, Post Renovation Photos Coming Soon
- 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 $580 per night (USD)VRBO
- From $555 per night (USD)
VRBO
Perfect Placement, Post Renovation Photos Coming Soon
- 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 $555 per night (USD)VRBO
- From $490 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 $490 per night (USD)VRBO
- From $500 per night (USD)
VRBO
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 $500 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $130 per night (USD)VRBO
- From $578 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 $578 per night (USD)VRBO
- From $160 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 $160 per night (USD)VRBO
- From $325 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 $325 per night (USD)VRBO
- From $149 per night (USD)
VRBO
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 $149 per night (USD)VRBO
- From $249 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 $249 per night (USD)VRBO
- From $115 per night (USD)
VRBO
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 $115 per night (USD)VRBO
- From $996 per night (USD)
VRBO
Flip Flops BEACH FRONT house and Sand Bar. \nMajestic panoramic views and sunsets
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful 2 story beach front house with ground floor Patio and Sand Bar. Home is located on the exclusive North Captiva ...
From $996 per night (USD)VRBO