Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $1027 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 $1027 per night (USD)VRBO
From $238 per night (USD)VRBO
Hurricane Ian update Roofs are on pools are heated life rolls on Thank God
- Bedrooms:
- 2
- 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 $238 per night (USD)VRBO
From $154 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 $154 per night (USD)VRBO
From $1200 per night (USD)Expedia
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Since 2017, "The Blue Marlin" has provided sea-loving families with the ultimate North Captiva beachfront retreat. This ...
From $1200 per night (USD)Expedia
From $814 per night (USD)VRBO
Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Newly remodeled (2025) Luxury 4 BR/5 BA - Brand New Kitchen and Baths – Close to beach, Island Club and Preserve, yet a ...
From $814 per night (USD)VRBO
From $186 per night (USD)Expedia
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ANGLER'S INN in Matlacha, Florida is a pet-friendly waterfront "Botel" accommodation located between Cape Coral and Pine ...
From $186 per night (USD)Expedia
From $115 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 $115 per night (USD)VRBO
From $912 per night (USD)VRBO
AWESOME HUGE BEACH HOUSE GREAT FLOOR PLAN VIEWS UPDATES CLUB!2 CARTS PETS
- Bedrooms:
- 3
- 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 $912 per night (USD)VRBO
From $400 per night (USD)VRBO
PERFECT FAMILY GETAWAY - 3 Bedroom/2 1/2 Bath with 60' Boat Dock & Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the delightful three-bedroom getaway nestled right within Saint James City. Imagine waking up to stunning ocean ...
From $400 per night (USD)VRBO
From $101 per night (USD)Expedia
Best Deal Available for a monthly rental home during season! 🏝️🐬
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
If you're looking to get out of the cold weather this winter, this is the perfect place to relax, fish, walk to the Blue ...
From $101 per night (USD)Expedia
From $149 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 $149 per night (USD)VRBO
From $176 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 $176 per night (USD)VRBO
From $239 per night (USD)VRBO
Beautiful, cozy, clean & fresh house on a canal with private ramp, spce to moore
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This house is located at the North of Pine Island, a tranquil, scenic, peaceful, tropical scenery. The area is renown fo ...
From $239 per night (USD)VRBO
From $693 per night (USD)VRBO
All Conched Out - Luxe 3 Br, Private pool, outdoor pool table - pets considered
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
All Conched Out This adorable “pink palace” retreat has everything you need for a fun, wonderful and relaxing vacation ...
From $693 per night (USD)VRBO
From $492 per night (USD)VRBO
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 $492 per night (USD)VRBO
From $171 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 $171 per night (USD)VRBO
From $808 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 $808 per night (USD)VRBO
From $239 per night (USD)Expedia
Tropical Island Resort Nestled on the Gulf Coast of Southwest Florida
- Bedrooms:
- 2
- 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 $239 per night (USD)Expedia
From $490 per night (USD)VRBO
CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning waterfront property in gorgeous Safety Harbor Club. Enjoy breathtaking views and the best the island has to off ...
From $490 per night (USD)VRBO
From $865 per night (USD)Expedia
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 18
Overview of the property: • No Worries Atoll is a stunning 3,300 square foot pool home. $1.5 million extensive renovati ...
From $865 per night (USD)Expedia
From $342 per night (USD)VRBO
2/2 Pool Home on the Water, Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Waterfront Paradise in St. James City | Heated Pool, Dock, Gulf Access 2 Bed | 2 Bath | Sleeps 4 | Boat Lift | Bikes | ...
From $342 per night (USD)VRBO
From $217 per night (USD)Expedia
Welcome to Porchfish! 3/2 in St. James City! Boat lift & Beautiful Views! No Hurricane Damage
- 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 $217 per night (USD)Expedia
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 $1048 per night (USD)Expedia
Tropical Family Oasis: Pool, Spa, Golf Cart – End of Year Deals & Specials!
- 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 $1048 per night (USD)Expedia
From $83 per night (USD)VRBO
Island Escape 2
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a two bedroom, one bathroom, 950 sq. ft. apartment, located on the first floor of a duplex. It is situated on a ...
From $83 per night (USD)VRBO
From $250 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 Escape to island paradise at Rum N Reel, your ultimate waterfront vacation ...
From $250 per night (USD)VRBO
From $1048 per night (USD)VRBO
Bluefin Beach House, Luxury Home with Pool & Spa on North Captiva, 2 Golf Carts
- Bedrooms:
- 4
- 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 $1048 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 $91 per night (USD)VRBO
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
- Bedrooms:
- 0
- 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 $91 per night (USD)VRBO
From $158 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 $158 per night (USD)VRBO
From $214 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 $214 per night (USD)VRBO
From $187 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Hook Studio". Compared ...
From $187 per night (USD)VRBO
From $177 per night (USD)VRBO
Studio on the Water. Great for monthly stays!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Rod Studio" that sleeps ...
From $177 per night (USD)VRBO
From $179 per night (USD)VRBO
Cottage with private deck in the heart of Matlacha
- Bedrooms:
- 1
- 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 $179 per night (USD)VRBO
From $213 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 $213 per night (USD)VRBO
From $743 per night (USD)Expedia
SeaStar North Captiva, Private Pool, Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Star is a exquisite new vacation beach home fully equipped and built to a high standard. The home is a spacious one ...
From $743 per night (USD)Expedia
From $572 per night (USD)VRBO
Great Island Retreat- Walk to Beach and Pools
- Bedrooms:
- 3
- 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 $405 per night (USD)Expedia
Townhome with stunning view of Matlacha Pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning Views….A unique town home community nestled on the island of Matlacha. This Matlacha location is literally minu ...
From $405 per night (USD)Expedia
From $435 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 $435 per night (USD)VRBO
From $1258 per night (USD)Expedia
Serendipity is BACK - Complete remodel April 2024 - Pool; 2 Golf Carts
- Bedrooms:
- 3
- 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 $1258 per night (USD)Expedia
From $284 per night (USD)VRBO
Peaceful home on canal with boat lift, hot tub, and 5 mins to Charlotte Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful and quiet waterfront home with amazing view, great fishing, and a hot tub to relax in after a nice day out on ...
From $284 per night (USD)VRBO
From $259 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 $259 per night (USD)VRBO
From $139 per night (USD)VRBO
Studio Redfish Room in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Redfish Room" in a house with 4 apartments, open water - cozy atmosphere in an open living-sleeping area with fu ...
From $139 per night (USD)VRBO
From $279 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 $279 per night (USD)VRBO
From $138 per night (USD)VRBO
Studio Snook Suite in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Apartment "Snook Suite" with 4 beds - open living / sleeping area - well equipped kitchen and dining area for 4 persons ...
From $138 per night (USD)VRBO
From $575 per night (USD)Expedia
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Immerse yourself in the idyllic charm of this three-story Key West style residence, perfectly situated to offer unsurpas ...
From $575 per night (USD)Expedia
From $769 per night (USD)VRBO
Private dock with 2 golf carts Oceanfront home Absolute Best Location on island!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
All brand new. Complete remodel. Be the 1st guest in. Located overlooking Safety Harbor. 2 Amazing decks overlooking the ...
From $769 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 $281 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 $281 per night (USD)VRBO
From $135 per night (USD)Expedia
Studio Tarpon Suite in Matlacha/Fisherman's Paradise
- 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 $135 per night (USD)Expedia
From $121 per night (USD)VRBO
Studio Grouper Room in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Grouper Room" - comfort in the smallest space - living, sleeping, cooking - ideal for singles and couples - well ...
From $121 per night (USD)VRBO
From $939 per night (USD)Expedia
Dolphin Cottage: Beachfront Home with Stunning Views & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Dolphin Cottage, a delightful beachfront retreat on North Captiva Island, known for its tranquil "Old Florida ...
From $939 per night (USD)Expedia
From $716 per night (USD)VRBO
Shell Yeah! - 3BR Home with Pool, Gulf Views & Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Shell Yeah!, your ultimate 3-bedroom beachfront escape on North Captiva Island. This newly renovated home is ...
From $716 per night (USD)VRBO
From $625 per night (USD)Expedia
159 - Flamingo House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Flamingo House, a lovely tropical retreat on North Captiva Island, offering a unique Gulfside getaway. This 3 ...
From $625 per night (USD)Expedia
From $1336 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 $1336 per night (USD)VRBO
From $190 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 $190 per night (USD)VRBO
From $279 per night (USD)VRBO
Private Pool & Deck: Canalfront St James City Home
- 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 $279 per night (USD)VRBO
From $1048 per night (USD)Expedia
South Side Tortuga Sunset Pool, Cart & Starlink – Limited-Time Year-End Savings!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Tortuga Sunset – Your Caribbean Escape on North Captiva Island! Transport yourself to paradise at Tortuga Su ...
From $1048 per night (USD)Expedia
From $239 per night (USD)VRBO
3 Minutes to Open Water! Great Fishing Retreat on Gulf-Access Canal! Over $125 Free Daily Activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Tarpon Camp in beautiful Bokeelia, FL - your own private retreat in the heart of the Tarpon Capital of the Wo ...
From $239 per night (USD)VRBO
From $274 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 $274 per night (USD)Expedia
From $115 per night (USD)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 ...
From $115 per night (USD)VRBO
From $206 per night (USD)Expedia
Bokeelia Cottage w/ Private Pool
- 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 $206 per night (USD)Expedia
From $909 per night (USD)VRBO
Manatee Manor: Exclusive Beachfront Retreat with Gulf Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Manatee Manor, your ultimate beachfront retreat on North Captiva Island. Situated in one of the island's most ...
From $909 per night (USD)VRBO
From $1013 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 $1013 per night (USD)VRBO
From $812 per night (USD)VRBO
5BR Island Home - Private Pool, Game Room & Golf Cart - Steps to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Island Splash is a 5-bedroom, 4-bath vacation home on the secluded North Captiva Island, offering an idyllic getaway for ...
From $812 per night (USD)VRBO
From $365 per night (USD)Expedia
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 $365 per night (USD)Expedia
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 $338 per night (USD)VRBO
LUXURY ISLAND RENTAL/CLUB w/POOL, KAYAKS, 3BR PRIV BEACH ACCESS, BOAT DOCK AVAIL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FANTASTIC NEW LUXURY ISLAND RENTAL! OPEN and WELCOMING GUESTS! ONE 6 PERSON GOLF CART INCLUDED COMPLIMENTARY AS AVAILABL ...
From $338 per night (USD)VRBO
From $562 per night (USD)VRBO
Coconut Castaway-Ocean Views, Golf Cart, Club Pool, Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**Once booked, you will need to complete and sign a vacation rental agreement** *Please note: We recognize, based on fee ...
From $562 per night (USD)VRBO
From $314 per night (USD)VRBO
Pet-Friendly Oasis w/ Deck & Fire Pit in Bokeelia!
- 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 $314 per night (USD)VRBO
From $1197 per night (USD)VRBO
SPRAWLING PRIVATE BEACHFRONT - Sleeps 10, perfect for a family, 2 golf carts
- Bedrooms:
- 3
- 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 $1197 per night (USD)VRBO
From $847 per night (USD)Expedia
\"FLORIDAYS\" Newly Completed Private Beach House w/ Heated Pool & Spa. 2 Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Photos updated December 2023 “FLORIDAYS" Completed in 2019, this new custom-designed and crafted 4 bedroom, 4 full bath ...
From $847 per night (USD)Expedia
From $237 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 $237 per night (USD)VRBO
From $340 per night (USD)Expedia
Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nice relaxing townhome…. Simple, white, clean…. A few steps from the harbors edge. Great place to escape from work, or ...
From $340 per night (USD)Expedia
From $373 per night (USD)VRBO
Bokeelia Island Oasis: Waterfront, Private Dock!
- 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 $373 per night (USD)VRBO
From $926 per night (USD)Expedia
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
*This property is located on North Captiva which is only accessible by ferry or boat. * Our home, Dreamcatcher, is on N ...
From $926 per night (USD)Expedia
From $121 per night (USD)VRBO
Studio Condo, just minutes from Charlotte Harbor and great island shopping!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Captains Cove waterfront end unit-Studio condo, 1 Bath, second floor, with parking under unit. Queen size Murphy bed an ...
From $121 per night (USD)VRBO
From $207 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 $207 per night (USD)VRBO
From $446 per night (USD)VRBO
TARPON COVE - Coastal island home on a golf cart only private island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fall 2025 Update! Thank you for your interest in Tarpon Cove. We’re happy to report that the island is recovering reall ...
From $446 per night (USD)VRBO
From $263 per night (USD)Expedia
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bring the boat, kayaks, bikes and water toys. This high and dry Pine Island home on a canal has withstood all the storms ...
From $263 per night (USD)Expedia
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
Heated Salt Water Pool and Spa on Marble Lanai, with large screened enclosure. This side-by-side home is fully equipped ...
From $243 per night (USD)VRBO
From $325 per night (USD)VRBO
Game Room & Deck: Spacious Home in St James City
- 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 $325 per night (USD)VRBO
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 $79 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 $79 per night (USD)VRBO
From $463 per night (USD)VRBO
Escape to private lakefront home, steps to gulf, with STARLINK HiSpeed Internet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Second Star is a peaceful place with a state-of-the-art interior, a unique 3 bedroom, 2 bath, 1450 sf home, nestled in p ...
From $463 per night (USD)VRBO
From $1202 per night (USD)Expedia
BLUE MANGO -- Tropical Seclusion Steps from the Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
"HURRICANE HELENE/MILTON UPDATE: We sustained only MINOR damage, mostly to the exterior landscape and are READY ...
From $1202 per night (USD)Expedia
From $158 per night (USD)VRBO
Island TreeTop House, Pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely cozy 2bed 1bath secluded house in quiet neighborhood. My home is very clean and uncluttered. Great for Two or t ...
From $158 per night (USD)VRBO
From $294 per night (USD)Expedia
Waterfront cottage in Matlacha, FL -<br>Unavailable at this time due to Hurr Ian.🌴
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our paradise cottage is in the cutest, artsiest, fishingest town, Matlacha FL, on Pine Island. Clean, updated and beauti ...
From $294 per night (USD)Expedia
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Beachfront🌊3 KING suites & bunk room🛏️Pet Friendly🐾
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Currently Under Renovation – Get Ready to Experience The All New Sunset Escape in Summer 2026! 👙GULF FRONT 180 ...
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From $328 per night (USD)VRBO
Calling Waters-Gulf access w/dock, pool and HT.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning canal front home in Southwest Florida features a heated pool, a private dock that can accommodate a 25-foo ...
From $328 per night (USD)VRBO
From $604 per night (USD)VRBO
Paradise Found/ North Captiva / Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape the crowds to a remote tropical island paradise that can only be accessed by ferry, private boat or small private ...
From $604 per night (USD)VRBO
From $166 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 $166 per night (USD)Expedia
From $122 per night (USD)VRBO
Studio Grouper Room in Matlacha/Fisherman's Paradise
- 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 $122 per night (USD)VRBO
From $453 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 $453 per night (USD)Expedia
From $829 per night (USD)VRBO
The Salty Conch - Luxury Just Steps To The Beach with Private Pool; Golf Cart
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Book your stay at the beautiful, new to the rental market, island house, just a short golf cart ride to the beach! The ...
From $829 per night (USD)VRBO
From $344 per night (USD)VRBO
The Perfect Day in Matlacha! Direct Gulf Access!
- Bedrooms:
- 2
- 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 $344 per night (USD)VRBO
From $729 per night (USD)VRBO
THE BIRDS & THE BEACH - 4 bed 3 bath, Sleeps 12, HUGE Private Pool, 2 GOLF CARTS
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
SPACIOUS 4 BR. 3 BATH - sleeps 12 in beds, 2 Golf Carts, PRIVATE HEATED POOL , Most of the house is completely new, ...
From $729 per night (USD)VRBO
From $250 per night (USD)Expedia
Beautiful Bokeelia!!!! Fishing dream! Bring your boat and your dog
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bokeelia property within walking distance to Bokeelia Fishing pier and boat launch. Smaller boats cane moor in our cove. ...
From $250 per night (USD)Expedia
From $311 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 $311 per night (USD)VRBO
From $137 per night (USD)VRBO
Studio snook Suite in Matlacha/Fisherman's Paradise
- 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 $137 per night (USD)VRBO