Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $1250 per night (USD)
VRBO
The MAINE DECK - BRAND NEW DESIGNER HOME WITH PRIVATE POOL AND 2 GOLF CARTS
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
BRAND NEW HOME - SCHEDULED FOR COMPLETION 02/28/2022 Welcome to the Maine Deck! Our beautiful dream home is brand new w ...
From $1250 per night (USD)VRBO
- From $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 $368 per night (USD)
VRBO
SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Golf Cart-Sleeps 7
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
SMUGGLERS HIDEAWAY is a secluded 3 bedroom island home located on North Captiva Island. Nestled among palm trees, the h ...
From $368 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Pet-Friendly \/ Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
ANGLER'S INN in Matlacha, Florida is a pet-friendly waterfront "Botel" accommodation located between Cape Coral and Pine ...
From $165 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 $350 per night (USD)
VRBO
pool house on 2 acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island stilt house,close to lavenderlanding boat ramp,jug creek and 4 winds marina,bokeelia pier, lazy flaming and capt ...
From $350 per night (USD)VRBO
- From $328 per night (USD)
Expedia
360 Views\/Direct Gulf Access w\/ 60' Boat Dock \/ Private Heated Pool\/Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
White Sands is a luxury custom built waterfront home completed in 2022. Heated pool and direct access to the Gulf of Mex ...
From $328 per night (USD)Expedia
- From $113 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 $113 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 $250 per night (USD)
VRBO
Pine island retreat in botanical oasis near Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this relaxing and tranquil getaway. Property located on a lush tropical oasis. Canal front with direct a ...
From $250 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 $193 per night (USD)
VRBO
Beautiful, cozy, clean & fresh house on a canal with private ramp, spce to moore
- Bedrooms:
- 2
- 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 $193 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 $347 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 $347 per night (USD)VRBO
- From $99 per night (USD)
VRBO
Has all of the modern comforts-hidden in the palm and mango groves.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for those seeking a peaceful retreat or just to get away for some time alone. This original Florida cracker-styl ...
From $99 per night (USD)VRBO
- Click For Pricing
VRBO
Happy Hours Beach House - Luxury, Pool, 2 Golf Cart New Property Managers! 4\/22
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
4 BR/4.5 BA Luxury Home – Heated Screened-In Pool - 2 golf carts - Membership to the North Captiva Island Club large sec ...
Click For PricingVRBO
- 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 $594 per night (USD)
VRBO
Island Daze: Modernized Kitchen and Endless Relaxation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whether you plan to fish, beach-comb, relax in the sun, play in the pool, enjoy nature or do nothing this is your ideal ...
From $594 per night (USD)VRBO
- From $167 per night (USD)
Expedia
Tropical Island Resort Nestled on the Gulf Coast of Southwest Florida
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Bocillia Island Club located in Bokeelia on the north-end of Pine Island on Florida’s west coast and the last of Old Flo ...
From $167 per night (USD)Expedia
- From $400 per night (USD)
VRBO
CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning waterfront property in Safety Harbor Club. Enjoy breathtaking views and the best the island has to offer at Cap ...
From $400 per night (USD)VRBO
- From $208 per night (USD)
Expedia
Snook Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Snook Suite Comfortable second-floor living room with queen size pull out sofa. Complete kitchen with microwave, ROKU T ...
From $208 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Tarpon Penthouse Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Deluxe "Tarpon" Penthouse One bedroom apartment Living Room with Cable TV Kitchen with Refrigerator Bathroom with Bath & ...
From $306 per night (USD)VRBO
- From $232 per night (USD)
Expedia
Seatrout Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Seatrout Suite Bedroom with shower, queen size bed, sitting room with futon, small complete kitchen with microwave and R ...
From $232 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Snapper Room Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Snapper Room King size bed, small refrigerator, microwave, ROKU TV and bathroom with shower. Mini fridge Microwave TV B ...
From $196 per night (USD)VRBO
- From $236 per night (USD)
Expedia
RedFish Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Redfish Suite Comfortable second-floor living room with plenty of seating. Complete kitchen, ROKU TV with DVD, 2 queen s ...
From $236 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 $103 per night (USD)
VRBO
Pelican`s Preserve in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this beautiful 2 bedroom 2 bath with a screened lanai and an open deck to enjoy views of the canal. Love boating? ...
From $103 per night (USD)VRBO
- From $162 per night (USD)
Expedia
3\/2 HEATED POOL HOME WITH BOAT LIFT! 3\/2 Waterfront, Pet Friendly Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This immaculate 3 bedroom, 2 bathroom home is waterfront with Direct Access to the Intra-coastal Waterway, your gateway ...
From $162 per night (USD)Expedia
- From $249 per night (USD)
VRBO
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 $249 per night (USD)VRBO
- From $216 per night (USD)
Expedia
RENTAL READY! Newly Renovated 2\/2 POOL Home with BOAT LIFT, INCREDIBLE ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Banana Haven! This immaculate, newly renovated 2 bedroom, 2 bathroom home is waterfront with direct access to ...
From $216 per night (USD)Expedia
- From $108 per night (USD)
VRBO
2\/2 Privacy in Pine Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Pineland is one of the most unique areas on Pine Island. It is beautiful and features the Randell Research Center which ...
From $108 per night (USD)VRBO
- From $179 per night (USD)
Expedia
Welcome to Porchfish! 3\/2 in St. James City! Boat lift, Corner Lot, Beautiful Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to peace, welcome to paradise, welcome to PORCHFISH! This beautiful 3 bedroom, 2 bath home on Pine Island in St. ...
From $179 per night (USD)Expedia
- 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 $550 per night (USD)
VRBO
Blue Heron * fish, boat, wine, dine, relax, repeat!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to the Blue Heron. This beautiful home will win your heart - a place to create amazing memories. Located in Boke ...
From $550 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Dream Screened Lanai & Pool 3+ months, Dream Screened Lanai
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a Home away from Home, in Sunny Florida. We are looking for you, if you want a 3+ month stay Jan-April 20 ...
From $295 per night (USD)VRBO
- From $746 per night (USD)
Expedia
Tropical Family Oasis: Green Tortuga
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
"Welcome to Green Tortuga: Your Tropical Oasis Awaits! Escape to Green Tortuga and experience the allure of the Caribbe ...
From $746 per night (USD)Expedia
- From $91 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 $91 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 $180 per night (USD)
VRBO
St. James City Vacation Home with Private Dock, Pool and Gulf Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Rum N Reel • St. James City Vacation Rental If you're looking for a fabulous waterfront vacation home with a private poo ...
From $180 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Guardalavaca , Boaters Paradise and Beachgoers Delight , New Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Salutations from the balcony in this secluded townhome as you watch the sunrise and breathe fresh ocean air. Come a ...
From $340 per night (USD)VRBO
- From $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 $160 per night (USD)
VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Hook Studio". Compared ...
From $160 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Studio on the Water. Great for monthly stays!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Rod Studio". We are loc ...
From $153 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 $553 per night (USD)
VRBO
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 $553 per night (USD)VRBO
- From $222 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 $222 per night (USD)Expedia
- 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 $300 per night (USD)
Expedia
Townhome with stunning view of Matlacha Pass
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning Views….A unique town home community nestled on the island of Matlacha. This Matlacha location is literally minu ...
From $300 per night (USD)Expedia
- 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 $1109 per night (USD)
Expedia
Island Queen, Luxury in Paradise, 200ft to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
If you are looking for the best pool and beach location, the Island Queen should be your next vacation destination! This ...
From $1109 per night (USD)Expedia
- 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 $110 per night (USD)
Expedia
Waterfront Matlacha Condo w\/ Patio + Pool Access!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience an 'Island Getaway' at this 2-bedroom, 2.5-bath end-unit condo in Matlacha! Nestled in a tropical landscape, ...
From $110 per night (USD)Expedia
- 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)
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 $273 per night (USD)Expedia
- 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 $103 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Studio "Redfish Room" in a house with 4 apartments, open water - cozy atmosphere in an open living-sleeping area with fu ...
From $103 per night (USD)VRBO
- 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 $103 per night (USD)
VRBO
REOPENED SINCE NOVEMBER 2023!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Apartment "Snook Suite" with 4 beds - open living / sleeping area - well equipped kitchen and dining area for 4 persons ...
From $103 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Matlacha\/Cape Coral - Kokopelli House - relax, it's your Island lifestyle
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three-story SW facing residence offers unsurpassed views of the bay. Put yourself on Island time in this beautifu ...
From $465 per night (USD)VRBO
- From $601 per night (USD)
Expedia
Private dock with 2 golf carts Oceanfront home Absolute Best Location on island!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
All brand new. Complete remodel. Be the 1st guest in. Located overlooking Safety Harbor. 2 Amazing decks overlooking the ...
From $601 per night (USD)Expedia
- 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 $87 per night (USD)
VRBO
BEST FISHING AREA \/ Fishing Kayaks available
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Studio "Grouper Room" - comfort in the smallest space - living, sleeping, cooking - ideal for singles and couples - well ...
From $87 per night (USD)VRBO
- From $540 per night (USD)
VRBO
Blue Macaw: 3 Bedroom Home Just a Block From the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
079 - Blue Macaw is a beautiful 3 bedroom home located just a block away from the beach. The home boasts an upside-down ...
From $540 per night (USD)VRBO
- From $514 per night (USD)
Expedia
Dolphin Cottage: Beachfront Home With Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Dolphin Cottage, an awesome 2-bedroom Bayfront home Just steps to your own private beach. Best fishing spot on the islan ...
From $514 per night (USD)Expedia
- From $519 per night (USD)
VRBO
128 - Shell Yeah! North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Upon arriving at Shell Yeah, your senses will be immediately captivated by the enchanting downstairs area, featuring a s ...
From $519 per night (USD)VRBO
- From $573 per night (USD)
Expedia
Flamingo House: Gulfside Getaway with Pool, Karaoke & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flamingo House is a lovely tropical home with a special island flair. Carved flamingos on the eaves, conch shells, pinea ...
From $573 per night (USD)Expedia
- From $1045 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 $1045 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 $244 per night (USD)
VRBO
Canalfront St James City Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Endless aquatic activities await at this St. James City vacation rental! This 3-bedroom, 2-bathroom home offers a Gulf C ...
From $244 per night (USD)VRBO
- From $411 per night (USD)
Expedia
Airstrip Ocean Oasis: Tortuga Sunset
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Tortuga Sunset – Your Caribbean Escape on North Captiva Island! Transport yourself to paradise at Tortuga Su ...
From $411 per night (USD)Expedia
- From $100 per night (USD)
VRBO
Saint James City Home w\/ Direct Water Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to Pine Island for a waterfront stay at this 3-bedroom, 2-bathroom vacation rental! The bright, comfortable inter ...
From $100 per night (USD)VRBO
- From $176 per night (USD)
Expedia
THREE Minutes to Open Water! Fantastic, Remodeled Fishing Retreat on Gulf-Access Canal, Free Wifi!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Tarpon Camp in beautiful Bokeelia, FL - your own private retreat in the heart of the Tarpon Capital of the Wo ...
From $176 per night (USD)Expedia
- From $230 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 $230 per night (USD)VRBO
- 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 $144 per night (USD)
Expedia
Bokeelia Cottage w\/ Private Pool & Tiki Bar!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Find a tropical paradise in your own backyard at this 2-bedroom, 2-bathroom Bokeelia vacation rental cottage! With all o ...
From $144 per night (USD)Expedia
- From $675 per night (USD)
VRBO
Manatee Manor: Your Ultimate Beachfront Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Directly on the beach in one of North Captiva's most exclusive locations, this architectural delight is truly a great pl ...
From $675 per night (USD)VRBO
- From $1162 per night (USD)
VRBO
The Green Flash: Gulf Front Home with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a tropical paradise with breathtaking views at Green Flash, a 4-bedroom Gulf front vacation home with a privat ...
From $1162 per night (USD)VRBO
- From $590 per night (USD)
VRBO
Island Splash: Private Pool and Air hockey, Fun for the Whole Family
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
082 - Island Splash is a fabulous 5 bedroom home was designed to accommodate groups up to 12 in comfort! With lots of ro ...
From $590 per night (USD)VRBO
- From $433 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 $433 per night (USD)VRBO
- From $112 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 $112 per night (USD)VRBO
- From $242 per night (USD)
VRBO
LUXE ISLAND RENTAL! CLUB AMENITIES, KAYAKS, 4BR, PRIV BEACH ACCESS DOCKAGE
- 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 $242 per night (USD)VRBO
- From $556 per night (USD)
VRBO
Coconut Castaway - Ocean Views, Walk to Beach, Golf Cart, Club Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
***Hurricane Update*** As of September 28, 2022 we are temporarily closed due to damages sustained from Hurricane Ian. W ...
From $556 per night (USD)VRBO
- Click For Pricing
Expedia
Coastal Bokeelia Oasis w\/ Pool, Deck & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hitch up your boat, gather the family, and embark on an unforgettable Florida adventure to this luxurious vacation renta ...
Click For PricingExpedia