
Calusa Land Trust and Nature Preserve of Pine Island Rentals

- From $724 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 $724 per night (USD)VRBO
- From $195 per night (USD)
VRBO
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 $195 per night (USD)VRBO
- From $398 per night (USD)
VRBO
Butterfly Breeze on North Captiva Island, Ask About Special Fall and Low Occupancy Rates
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to your own slice of island paradise at Butterfly Breeze – a luxurious retreat just moments away from the beach o ...
From $398 per night (USD)VRBO
- From $329 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 $329 per night (USD)Expedia
- From $291 per night (USD)
VRBO
Fun'n Sun-Charming 3 BR/3 baths waterfront villa- pool, spa, dock, fishing poles
- 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 $291 per night (USD)VRBO
- From $793 per night (USD)
Expedia
Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Captiva Beach Sunset 5 BR / 4.5 BA | Sleeps 15 in beds (plus 2 twin recliners, perfect for kids!) | Beachfront | Private ...
From $793 per night (USD)Expedia
- From $138 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 $138 per night (USD)VRBO
- From $192 per night (USD)
Expedia
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
- Bedrooms:
- 2
- 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 $192 per night (USD)Expedia
- From $636 per night (USD)
VRBO
LUNAR TIDES - 3 BR/2 BA - Your dream vacation spot! Private Pool - 1 Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your dream vacation to an island paradise is just a few clicks away! Lunar Tides is located on the barrier island of No ...
From $636 per night (USD)VRBO
- From $1052 per night (USD)
Expedia
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 $1052 per night (USD)Expedia
- From $159 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 $159 per night (USD)VRBO
- From $261 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 $261 per night (USD)Expedia
- From $552 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 $552 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Pelican`s Preserve in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this beautiful 2 bedroom 2 bath with a screened lanai and an open deck to enjoy views of the canal. King bedroom i ...
From $209 per night (USD)Expedia
- From $268 per night (USD)
VRBO
3/2 Heated Pool, Waterfront w/ Boat Lift!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*No Hurricane Helene or Milton Damage* Fresh and airy pool home on the water in St. James City! This property offers 3 b ...
From $268 per night (USD)VRBO
- From $296 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 $296 per night (USD)Expedia
- From $101 per night (USD)
VRBO
2/2 Privacy in Pine Island!
- Bedrooms:
- 1
- 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 $101 per night (USD)VRBO
- From $206 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 $206 per night (USD)Expedia
- 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 If you're looking for a fabulous waterfront vacation home with a private poo ...
From $250 per night (USD)VRBO
- From $449 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 $449 per night (USD)Expedia
- From $1618 per night (USD)
VRBO
Tropical Family Oasis: Pool, Spa, Golf Cart
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Green Tortuga: Your Tropical Oasis Awaits! Escape to Green Tortuga and experience the ultimate Caribbean get ...
From $1618 per night (USD)VRBO
- From $263 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 $263 per night (USD)Expedia
- From $543 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 $543 per night (USD)VRBO
- From $769 per night (USD)
Expedia
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)Expedia
- From $661 per night (USD)
VRBO
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 $661 per night (USD)VRBO
- From $618 per night (USD)
Expedia
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 $618 per night (USD)Expedia
- From $587 per night (USD)
VRBO
Flamingo House: Gulfside Getaway with Pool & Golf Cart Included
- 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 $587 per night (USD)VRBO
- From $1431 per night (USD)
Expedia
Key Lime Time: Private Pool and Panoramic Gulf Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 169 - Key Lime Time, a stunning 5 bedroom, pool home with breathtaking Gulf views on North Captiva Island. Th ...
From $1431 per night (USD)Expedia
- From $215 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 $215 per night (USD)VRBO
- From $188 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 $188 per night (USD)Expedia
- From $727 per night (USD)
VRBO
Manatee Manor: Exclusive Beachfront Retreat with Gulf Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Manatee Manor, your ultimate beachfront retreat on North Captiva Island. Situated in one of the island's most ...
From $727 per night (USD)VRBO
- From $690 per night (USD)
Expedia
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 $690 per night (USD)Expedia
- From $510 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** Welcome to Coconut Castaway, your idyll ...
From $510 per night (USD)VRBO
- From $346 per night (USD)
Expedia
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 $346 per night (USD)Expedia
- From $1008 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 $1008 per night (USD)VRBO
- From $218 per night (USD)
Expedia
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 $218 per night (USD)Expedia
- From $300 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 $300 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 $225 per night (USD)
VRBO
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 $225 per night (USD)VRBO
- From $373 per night (USD)
Expedia
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)Expedia
- From $760 per night (USD)
VRBO
Fully renovated Luxury Beach House w pool! HUGE 5 BD 5 BA 9 beds! Sleeps 16+!
- 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 $760 per night (USD)VRBO
- From $154 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 $154 per night (USD)VRBO
- From $245 per night (USD)
VRBO
The Quarterdeck Cottage~Boat dockage available directly across the street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With dockage (across the street at my privately owned property) and golf carts available for your stay (additional fee)B ...
From $245 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Cozy, clean duplex with outdoor dinning.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Have your vacation in Paradise! This duplex is located in the heart of Pine Island a couple of blocks of the four way st ...
From $139 per night (USD)Expedia
- From $259 per night (USD)
VRBO
Yellow Fin Cabin of Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Famous Matlacha island with tourism and fishing. Many restaurants and bars at walking distance. The best fishing off a b ...
From $259 per night (USD)VRBO
- From $208 per night (USD)
Expedia
Dog-Friendly, Canal-Front Home with Canal Access, Central AC, and WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Flamingo Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $208 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful Monthly Condo at the Buccaneer. Minutes from off shore fishing.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The one bedroom one bathroom condo available minutes from Matlacha Florida. The Buccaneer is located on Pine Island and ...
Click For PricingVRBO
- From $171 per night (USD)
VRBO
The Crab Shack - Fully-equipped and Updated 2-bedroom Waterfront Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
* We survived IAN, we have completely remodeled and are back to being fully functional. ** Get away to the Crab Shack, ...
From $171 per night (USD)VRBO
- From $669 per night (USD)
VRBO
Windows on the Water \"W.O.W\" An ocean front oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
House, 3 bedrooms - 3 full bath. Our renovated home is named "Windows on the Water" because of the spectacular wall of ...
From $669 per night (USD)VRBO
- From $251 per night (USD)
Expedia
Waterfront condo located in the waterfront paradise of Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Incredible waterfront views in this fully stocked Bocilla Island Club condominium. This is an end unit which gives a pan ...
From $251 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Pine Island Private Getaway with Dock! (CDC Safe)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Absolutely the best location and value on Pine Island! Beautifully designed, spacious and private two bedroom home with ...
From $193 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Piece of Paradise for All Seasons!!! Bring Your Boat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Castaway Cottage is waiting for you! Come enjoy fishing and boating, or just relax with a cocktail in the screened lanai ...
From $239 per night (USD)Expedia
- From $761 per night (USD)
VRBO
Kaya Del Sol, the perfect family trip!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a magical island paradise! This quintessential family or couples' retreat inspires a relaxed peaceful ambience ...
From $761 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Well Equipped Pet/Smoke Free Family Home - bring your boat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
WE DON'T LIVE IN A SQUARE WORLD, WHY VACATION IN A SQUARE HOUSE? Come and experience the unique feel of a round house de ...
From $225 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Reel Paradise! 2/2 with So Much Waterfront! Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom two bath incredible home with water views from all angles! Large lot including, tiki wet-bar, plenty of spac ...
From $251 per night (USD)VRBO
- From $253 per night (USD)
Expedia
Waterfront Petite Retreat with Private Pool & Gulf Access - Villa Boat House - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Boat House Escape to paradise with this petite retreat villa featuring a private heated Pool & DIRECT Gulf Acces ...
From $253 per night (USD)Expedia
- From $411 per night (USD)
VRBO
Island Paradise: Steps to Private Gulf Beaches, Pools, Hot Tub & Golf Cart ALL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
North Captiva Retreat A Whisper Away from Pristine Gulf Shores Elevate your Florida vacation by choosing our 2-bedroom, ...
From $411 per night (USD)VRBO
- From $1194 per night (USD)
VRBO
Gulf of America Beach House, Private Pool, 360 Island Views Airstrip Membership
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Perfect Landing on North Captiva Island. 4 bedroom 3 bath.. 3 King suites plus bunkroom. Owner has Airstrip membership a ...
From $1194 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Matlacha Island Cottage w/ Dock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to 'Breezy's Hangout' where all you need for a good time is your sunglasses and swimsuit. Located just blocks fr ...
Click For PricingVRBO
- From $421 per night (USD)
Expedia
Treetops: Bright Island Home with Golf Cart & Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Treetops, an elegant and bright island home on North Captiva Island, perfect for a quick getaway. This 3-bedr ...
From $421 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Modern Villa SW of Cape Coral in quiet Surfside Blvd area with gulf access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Privacy, silence and relaxation are guaranteed at Villa Eyleen, located at one of the widest canals in Cape Coral. The r ...
From $286 per night (USD)VRBO
- Click For Pricing
Expedia
Great Winter Get Away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy refuge is Waterfront both sides right on Back Bay in Bokeelia. Your boat dock is 10 paces from your front door ...
Click For PricingExpedia
- From $242 per night (USD)
VRBO
Direct Gulf Access Island Retreat - Boat Lift, No Bridges, Convenient Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing, spacious stilt home offers 2 bedrooms and 2 bathrooms, Direct Gulf Access, Covered Boat Lift, gorgeous vie ...
From $242 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Luxury in Paradise!! Tropical Island Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully Appointed Home in Bokeelia. Lots of light. Peaceful, private and relaxing atmosphere at one with nature. The ...
From $242 per night (USD)Expedia
- From $879 per night (USD)
VRBO
Private & Spacious [2300sqft] home w/Pool,Hot Tub,Golf Cart, Pet Friendly & Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Complete exterior renovation completed March 2023 Welcome to our home on North Captiva Island. Remote and undiscovered, ...
From $879 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Welcome to Seabatical a barrier island get-away accessible only by boat or ferry
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy North Captiva Island! Seabatical, 3BR/2BA townhouse, with great views waiting for you to enjoy sitting on the scre ...
From $385 per night (USD)Expedia
- From $205 per night (USD)
VRBO
NEWLY REMODELED-Peaceful Florida Island Home-5 minute canal ride to Gulf waters!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Come relax in our Pine Island dream home--a charming, open and colorful floor plan will remind you that you are on a Flo ...
From $205 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Island Home within the Pines and Palms; Kayaks, Bikes, and Inviting Porches~
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Unique custom-built Key West style piling home with outdoor shower, plentiful parking underneath as well as long drivewa ...
From $180 per night (USD)Expedia
- Click For Pricing
VRBO
You are on the Henley canal, in Saint James.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The location is awesome here. You are minutes away from Sanibel and Captiva by boat. Bring your boat, the ramp and slip ...
Click For PricingVRBO
- From $403 per night (USD)
Expedia
(NO STORM DAMAGE AVAILABLE FOR IMMEDIATE RENTAL) BEAUTIFUL GULF ACCESS HOME .
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***UPDATED PICS 11/10/24 Immaculate saltwater canal Gulf access with no bridges minutes from open water. It doesn't get ...
From $403 per night (USD)Expedia
- From $712 per night (USD)
VRBO
Hidden Treasure - near Beach-Pool- Club Use - Dock available - 10% off weekly !!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
X marks the spot! Choose Hidden Treasure for your ultimate Island Getaway. Tucked away on at the end of a quiet cul-de- ...
From $712 per night (USD)VRBO
- From $790 per night (USD)
Expedia
SERENITY NOW~1 Min. To BEACH!-SCREENED-IN HEATED POOL-2 Carts-4&6, Island Club
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
SERENITY NOW has Gulf Sunrises and expanded Harbour views! luxurious 6~ bedrooms (4 Kings) 5~ full bathroom, 2 Golf Cart ...
From $790 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Adorable Waterfront Condo, Boat Slip and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Pine Island in Southwest Florida is a year-round getaway. Whether you are escaping a cold winter, or heading to the coas ...
From $338 per night (USD)VRBO
- From $460 per night (USD)
Expedia
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 $460 per night (USD)Expedia
- From $331 per night (USD)
VRBO
My Sea Shack~ 1 minute to beach, SH Club access, golf cart
- Bedrooms:
- 3
- 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 $331 per night (USD)VRBO
- From $436 per night (USD)
Expedia
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 $436 per night (USD)Expedia
- From $262 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 $262 per night (USD)VRBO
- From $348 per night (USD)
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 ...
From $348 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Waterfront Matlacha Home w/ Hot Tub & Grill!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fall into a routine of sunbathing, boating, and enjoying the Florida gulf breeze from the comfort of this Matlacha Islan ...
From $297 per night (USD)VRBO
- From $176 per night (USD)
Expedia
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 $176 per night (USD)Expedia
- From $791 per night (USD)
VRBO
Stella Marris- N. Captiva Island | Luxury Beachfront Retreat
- Bedrooms:
- 6
- Bathrooms:
- 3
- Sleeps:
- 6
Stella Maris - N. Captiva Island | Luxury Beachfront Retreat Discover ultimate seclusion at Stella Maris, our luxury Nor ...
From $791 per night (USD)VRBO
- From $212 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 $212 per night (USD)Expedia
- From $527 per night (USD)
VRBO
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 ...
From $527 per night (USD)VRBO
- From $992 per night (USD)
Expedia
Flamingo Beach: Beachfront Home with Endless Relaxation & Gulf Views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Flamingo Beach House, your ultimate beachfront retreat on North Captiva Island. This luxurious 5-bedroom home ...
From $992 per night (USD)Expedia
- From $280 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 $280 per night (USD)VRBO
- From $173 per night (USD)
Expedia
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 $173 per night (USD)Expedia
- From $394 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 $394 per night (USD)VRBO
- From $279 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 $279 per night (USD)Expedia
- From $230 per night (USD)
VRBO
First-floor, snowbird-friendly townhouse w/ shared pool, WiFi, central AC, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mermaid Haven at Bocilla Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $230 per night (USD)VRBO
- From $375 per night (USD)
Expedia
The Blue Pearl-walk to beach, 3B/2B with screened porch, and NCIC (pools & more)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This cute open concept home is great for gathering, relaxing, and making memories. Stroll just a few minutes to the whit ...
From $375 per night (USD)Expedia
- From $905 per night (USD)
VRBO
4 Bedroom Beach Home on a Private Island with a Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy spectacular views of Captiva Pass and Pine Island Sound from this professionally decorated Tropical Island Beach h ...
From $905 per night (USD)VRBO
- From $260 per night (USD)
Expedia
SEASIDE VILLA MANATEE BAY in quiet location on Pine Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the Island Life in our sun filled vacation home located off Manatee Bay, just north of Saint James City on Pine Is ...
From $260 per night (USD)Expedia
- From $739 per night (USD)
VRBO
Dream house near the beach, private pool, steps from the beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Coquina Beach House - a five bedroom house, in North Captiva. North Captiva is a private Island, just a sh ...
From $739 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Beautiful waterfront Key West style home with a pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Private, spacious Key West style home located on a canal with quick access to the pine Island sound. 3 bedroom 3 full ...
From $338 per night (USD)Expedia
- Click For Pricing
VRBO
Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
It’s an authentic Florida paradise! This special place is close to everything, making it easy to plan your visit whethe ...
Click For PricingVRBO
- From $264 per night (USD)
Expedia
Island Vibe! 3/2 Salt Water Heated Pool with Bonus Room, Waterfront!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Island Vibe! Gorgeous 3 bedroom two bath with heated salt water pool with incredible Gulf access is your perf ...
From $264 per night (USD)Expedia
- From $1054 per night (USD)
VRBO
Manatee Haven: Screened-in Pool, Spa and Elevator! 2 Golf Carts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Manatee Haven has been fully rebuilt and renovated post Hurricane Ian. The house is spectacular. Manatee Have ...
From $1054 per night (USD)VRBO
- From $279 per night (USD)
Expedia
Bokeelia Retreat - Fishing Docks & Canals Nearby!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Prepare for rest and relaxation when you book a stay at this 3-bedroom, 2-bathroom vacation rental home in Bokeelia! Loc ...
From $279 per night (USD)Expedia
- From $169 per night (USD)
VRBO
Pine Island Bokeelia, Twin Palms a 2 Bedroom, 2 Bath Home on Canal
- Bedrooms:
- 1
- 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 $169 per night (USD)VRBO
- From $494 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 $494 per night (USD)VRBO