Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $360 per night (USD)
VRBO
Beautiful house \/ charming Island \/ great fishing, manatees, dolphins. NO LANAI
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Grandpa Rudy first came to Pine Island in 1954 and our family has been coming ever since! Grab a cup of coffee (tea or ...
From $360 per night (USD)VRBO
- From $216 per night (USD)
VRBO
Peaceful, Family friendly Home w Pool, dock space & quick access to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful & Fun Family friendly home with 3 bedrooms enough to sleep 8 comfortably. There is an entertainment area with ...
From $216 per night (USD)VRBO
- From $156 per night (USD)
VRBO
Condo w use of a 10k boat lift. 5min to open water. Tarpon capital 15min away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Marina Gardens located on a peninsula surounded by Jug Creek in Bokeelia at the north-end of Pine Island on Florida's we ...
From $156 per night (USD)VRBO
- From $126 per night (USD)
Expedia
Charming & sun-filled condo with pool, W\/D, AC, & balcony - steps from the beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Bokeelia Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $126 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Modern Renovation~Club Pool👙 Kayaks🛶 Golf Cart🚙 Boat Dock⛵️ Private Beach🏖️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A true gem tucked away off the coast of Florida, North Captiva, also known as Upper Captiva Island is an adventure to ge ...
From $400 per night (USD)VRBO
- From $179 per night (USD)
Expedia
Treasure Cove Serenity! 3\/2 with Boat Lift, Beautiful New Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly built home has everything you need to make your stay in St. James City perfect. Brand new appliances and furn ...
From $179 per night (USD)Expedia
- Click For Pricing
Expedia
Dream Island Home Sum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover Pine Island, Florida's hidden gem, in this spacious home boasting high-end finishes. Explore the sceni ...
Click For PricingExpedia
- From $200 per night (USD)
VRBO
Peaceful retreat. Fishing Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful place to stay. Located in 1.04 acre of land this 3 bedrooms and two bathro ...
From $200 per night (USD)VRBO
- From $150 per night (USD)
VRBO
New waterfront Pine Island home awaits your fishing adventure!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our newly constructed waterfront house on Pine Island, located in the serene Charlotte Shore area of Bokeelia, FL, is n ...
From $150 per night (USD)VRBO
- From $800 per night (USD)
Expedia
ABSOLUTELY MAGNIFICENT! BEACH HOME PRIVATE POOL 2 GOLF CARTS\nHERE COMES THE FUN!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
HERE COMES THE FUN! Doo-d-doo-doo FUN FUN FUN Here it Comes! is a new single story 3-bedroom, 3 bathroom home. Finished ...
From $800 per night (USD)Expedia
- Click For Pricing
VRBO
Very private, 3 decks, a pond with many birds. Island living, access to mainland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very private on one acre of land with no neighbors, wild peacocks, ibis, herrons, Eagles woodpeckers, cardinals, ducks, ...
Click For PricingVRBO
- From $255 per night (USD)
Expedia
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 $255 per night (USD)Expedia
- From $283 per night (USD)
VRBO
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 $283 per night (USD)VRBO
- From $118 per night (USD)
Expedia
Aaliyah`s and Amina`s Tropical Retreat - Pine Island St James City Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $118 per night (USD)Expedia
- From $113 per night (USD)
VRBO
Pine Island - Lina`s Tropical Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to what we call ... Lina's Tropical Retreat on beautiful St James City, Florida. We're located within Pine Islan ...
From $113 per night (USD)VRBO
- From $119 per night (USD)
Expedia
Aaliyah`s and Amina`s Tropical Retreat unit 2 - Pine Island St James City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $119 per night (USD)Expedia
- From $113 per night (USD)
VRBO
Aaliyah`s and Amina`s Tropical Retreat 4 - Pine Island St James City Florida
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Named after our daughters as this reminds me of paradise in our beautiful Pine Island, St James City oasis. Aaliyah's an ...
From $113 per night (USD)VRBO
- From $212 per night (USD)
Expedia
First-floor, snowbird-friendly townhouse w\/ shared pool, WiFi, central AC, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Mermaid Haven at Bocilla Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $212 per night (USD)Expedia
- From $360 per night (USD)
VRBO
The Blue Pearl-walk to beach, 3B\/2B with screened porch, and NCIC (pools & more)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cute open concept home is great for gathering, relaxing, and making memories. Stroll just a few minutes to the whit ...
From $360 per night (USD)VRBO
- From $919 per night (USD)
Expedia
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 $919 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $750 per night (USD)
Expedia
North Captiva Island home, private pool, few steps from the beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Coquina Beach House - a five bedroom house, in North Captiva. North Captiva is a private Island, just a sh ...
From $750 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Quaint Waterfront Cottage Near Beaches and Fishing
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
REPAIRS ARE COMPLETE AND WE ARE READY TO RENT!!! Newly renovated cottage with rustic charm. Overlook the mangroves and ...
From $165 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Beautiful waterfront Key West style home with a pool
- Bedrooms:
- 4
- 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 $292 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Breathtaking Views! Sunsets and kayaks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Complimentary tandem kayak! It’s authentic Florida paradise! This special place is close to everything, making it eas ...
From $125 per night (USD)VRBO
- From $141 per night (USD)
Expedia
The heart of Matlacha! Remodeled and new bathroom!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Quick stroll to every Matlacha restaurant, bar, art galleries, & shops! This historic Matlacha Cottage has been restored ...
From $141 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Island Vibe! 3\/2 Salt Water Heated Pool with Bonus Room!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Island Vibe! Brand new look! Gorgeous 3 bedroom two bath with heated salt water pool with incredible Gulf acc ...
From $175 per night (USD)VRBO
- Click For Pricing
Expedia
Cute Bungalow Trailer on Canal in Flamingo Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Summary: Pocket Full Of Shells is located on the barrier island of North Captiva Island, Pocket Full Of Shells ...
Click For PricingExpedia
- From $930 per night (USD)
VRBO
Manatee Haven: Screened-in Pool, Spa and Elevator! 2 Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Manatee Haven Beach House is located on the exclusive barrier island of North Captiva Island, Manatee Haven is ...
From $930 per night (USD)VRBO
- From $159 per night (USD)
VRBO
Immaculate Waterfront Home With Heated Pool. Pet Friendly.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to St. James City on historic Pine Island to enjoy this beautifully renovated 2 bedroom canal home with a gorgeou ...
From $159 per night (USD)VRBO
- From $113 per night (USD)
VRBO
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 $113 per night (USD)VRBO
- Click For Pricing
Expedia
Ebb Tide - Your North Captiva Island Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The pristine beach. The spectacular fishing. The easy boating. The amazing shelling. The unbelievable flora and faun ...
Click For PricingExpedia
- From $94 per night (USD)
VRBO
2\/2 Cherry Estates Vacation Perfection
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Your next getaway awaits at the beautiful Cherry Estates in St. James City, FL. Our inviting 2-bedroom, 2-bathroom home ...
From $94 per night (USD)VRBO
- From $245 per night (USD)
Expedia
Paradise Found: 3\/2 Home with Pool, Canal Access, and Pet-Friendly Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the comfort and convenience of our exceptional ground level vacation rental home. Nestled on the Monroe Canal ...
From $245 per night (USD)Expedia
- From $272 per night (USD)
VRBO
2\/2 Waterfront home with pool and boat lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A gorgeous 2-bedroom, 2-bathroom mobile home located in the picturesque St. James City, FL. This charming retreat offers ...
From $272 per night (USD)VRBO
- From $286 per night (USD)
Expedia
3 Master Suites-EVERYTHING is new pool home on the water
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our amazing waterfront vacation home, where luxury and comfort await you. This newly renovated retreat featur ...
From $286 per night (USD)Expedia
- From $150 per night (USD)
VRBO
2 bed\/ 2.5 bath Waterfront Condo with 2 pools and great fishing
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the ultimate comfort and relaxation at this beautifully remodeled garden front condo. With its inviting ambia ...
From $150 per night (USD)VRBO
- From $67 per night (USD)
Expedia
1 bedroom,1 bath condo, Community heated pool and dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the perfect Winter getaway in Saint James City, FL with our inviting 1-bedroom, 1-bathroom condo. Located in a ...
From $67 per night (USD)Expedia
- From $150 per night (USD)
VRBO
2\/2.5 condo with docking available for your boat and pools for soaking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the picturesque shores of Charlotte Harbor and experience a vacation like no other. This stunning 2-bedroom, 2 ...
From $150 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Terrific vacation home on quiet Clipper Lane 2\/2 pool home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this remarkable vacation home nestled on peaceful Clipper Lane, just off of Sanibel Blvd. in the charming town ...
From $217 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Boater’s Paradise! Beautiful Home on the Water with 2 Boat Lifts & Dockage Space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful Newly Remodeled Home located right On the Water in Florida’s Best Kept Secret… Bokeelia In Pine Island, FL. Th ...
From $299 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Matlacha Sunset Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our beautiful newly renovated cottage just returned to the market in March 2024. Enjoy wide open water views with beauti ...
From $209 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Private Villa, 3 King Beds, Pool, Elevator, close to Ferry for Barrier Islands
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Palm Tree Villa on Pine Island, located on South-West Florida's Gulf of Mexico Coast. This spacious 3400 sq f ...
From $292 per night (USD)VRBO
- From $372 per night (USD)
Expedia
“Coral Cottage”<br>A Cottage Secluded in Palms with a Jacuzzi 2 minute walk 2 Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, ...
From $372 per night (USD)Expedia
- From $600 per night (USD)
VRBO
The Salty Snook
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unique Gulf Front and View Home : Private Dockage for up to 30 Foot Boat available...Perfect Florida Fishing Get Away. ...
From $600 per night (USD)VRBO
- From $200 per night (USD)
Expedia
The Blue Lagoon With Heated Pool \/on the Canal With NEW Boat Lift and Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please come and enjoy our 2BR / 2BA 1410 Sq ft. POOL home located in the quaint fishing village of Matlacha. ...
From $200 per night (USD)Expedia
- From $239 per night (USD)
VRBO
Spacious home hot tub, bring boat pacman dock Xtra parking. Walk 2 restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Gulf Access- Embrace the perfect fishing vacation spot for small or larger groups that won't break the bank. Weekley & m ...
From $239 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Private beach oasis -- 2-minute walk to the ocean! w\/ Golf Cart & Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The first thing you See or should we say "Sea" is the breathtaking Gulf of Mexico from virtually everywhere from each r ...
From $650 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Captiva Beach Sunset ~Gulf front, pool, NCIC, 4 & 6 seater carts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Captiva Beach Sunset - 5 BR/4.5 BA - Sleeps 12 in beds- Beachfront with Private Pool Queen size air mattress is availabl ...
From $1400 per night (USD)VRBO
- From $119 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 $119 per night (USD)VRBO
- From $157 per night (USD)
VRBO
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
- Bedrooms:
- 3
- 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 $157 per night (USD)VRBO
- From $500 per night (USD)
Expedia
LUNAR TIDES - 3 BR\/2 BA - Your dream vacation spot! Private Pool
- 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 $500 per night (USD)Expedia
- From $192 per night (USD)
VRBO
Beautiful Waterfront Ideal for fishing and boating!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a fisherman;s paradise with a boat lift, and you are only minutes from the waters of Pine Island Sound. This ar ...
From $192 per night (USD)VRBO
- From $157 per night (USD)
VRBO
Walking, biking, boating, local dining and friendly people on Pine Island!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This immaculate, well-kept condo has 2 bedrooms with in-suite bathrooms, two balconies, 2 pools and tennis courts. Resta ...
From $157 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Romantic beach home with golf cart kayaks and bikes. Remodeled Coastal charm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing property , newly renovated vacation home with 1800 square feet for you to enjoy , all air conditioned . Enjoy i ...
From $350 per night (USD)VRBO
- From $150 per night (USD)
Expedia
SANDY TUNDRA TOWNHOUSE, WATER-VIEWS, BOAT SLIP, PRIVATE BEACH, CLUB ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SANDY TUNDRA is a luxurious 3 bedroom waterfront townhouse with Safety Harbor Club access and the use of a private boat ...
From $150 per night (USD)Expedia
- From $708 per night (USD)
VRBO
TIPSY TURTLE - awesome pool, 4 decks, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
We’d like to welcome you to…Tipsy Turtle! TIPSY TURTLE - Located on North Captiva Island; this property is accessed by f ...
From $708 per night (USD)VRBO
- From $238 per night (USD)
Expedia
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 $238 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come, enjoy this 3 bedroom/2 bath 2000 sq.ft. home in Saint James City with over 300 feet of seawall. This Villa is a fi ...
From $179 per night (USD)VRBO
- From $561 per night (USD)
VRBO
The Wheelhouzz - Luxury Island Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Wheelhouzz is a beautiful three-bedroom beach property in Safety Harbor Club on North Captiva Island. It is privatel ...
From $561 per night (USD)VRBO
- From $104 per night (USD)
VRBO
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 $104 per night (USD)VRBO
- From $189 per night (USD)
Expedia
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 $189 per night (USD)Expedia
- From $180 per night (USD)
VRBO
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 $180 per night (USD)VRBO
- From $150 per night (USD)
Expedia
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 $150 per night (USD)Expedia
- From $302 per night (USD)
VRBO
Waterfront Haven w\/ Floating Dock, Alfresco Living, Two Suites & Yard for Dog
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Matlacha Mermaid Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $302 per night (USD)VRBO
- From $126 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 $126 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 $154 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 $154 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Windows on the Water \"W.O.W\" An ocean front oasis!
- Bedrooms:
- 4
- 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 $850 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Waterfront condo located in the waterfront paradise of Bokeelia
- Bedrooms:
- 3
- 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 $235 per night (USD)Expedia
- From $165 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 $165 per night (USD)VRBO
- From $150 per night (USD)
VRBO
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 $150 per night (USD)VRBO
- From $558 per night (USD)
VRBO
Kaya Del Sol, the perfect family trip!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a magical island paradise! This quintessential family or couples' retreat inspires a relaxed peaceful ambience ...
From $558 per night (USD)VRBO
- From $124 per night (USD)
Expedia
Sophisticated home with private pool & fast WiFi - walk & ferry to attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Eagles Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $124 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Canalfront St James City Home w\/ Unique View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The sand and sun await when you escape to this charming vacation rental. In addition to 2 bedrooms, 1 bathroom, and a su ...
From $331 per night (USD)VRBO
- From $318 per night (USD)
VRBO
Perfectly Located Island Unit in Matlacha Isles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Located on Matlacha Isles, this 2nd story unit is perfect island location and also easy to access all the ameni ...
From $318 per night (USD)VRBO
- From $180 per night (USD)
VRBO
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 Pool & DIRECT Gulf Access! Vill ...
From $180 per night (USD)VRBO
- From $283 per night (USD)
Expedia
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 $283 per night (USD)Expedia
- From $1273 per night (USD)
VRBO
Gulf of Mexico Beach House, Private Pool, 360 Island Views, Airstrip Membership
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Spectacular Beach House on North Captiva Island. 3 minute walk to the beach! Owner has Airstrip membership available for ...
From $1273 per night (USD)VRBO
- From $576 per night (USD)
Expedia
FlipFlopper Beach House - 3 Min to The Beach - Golf Carts and Club Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Well appointed family focused beach home only a 3 minutes walk from the White Sand Beaches on the Gulf of Mexico and 5 m ...
From $576 per night (USD)Expedia
- From $133 per night (USD)
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 ...
From $133 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Treetops: Comfortable Island Home with Golf Cart Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are looking for a quick getaway Treetops is a elegant bright beach house on North Captiva, has 3 bedrooms 2 bathr ...
From $359 per night (USD)Expedia
- From $238 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 $238 per night (USD)VRBO
- From $179 per night (USD)
VRBO
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 $179 per night (USD)VRBO
- From $9999 per night (USD)
VRBO
3\/2 in Bokeelia with INCREDIBLE GULF ACCESS, BOAT SLIP INCLUDED! Spacious upstairs unit with amazing porch overlooking canal!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a rental in Bokeelia? Look no further than PortoBello-21! This property is located at the end of a canal tha ...
From $9999 per night (USD)VRBO
- From $721 per night (USD)
Expedia
🌀IAN Updated🌀 Private Pool\/Hot Tub💦 Golf Carts 🚙 Pet Friendly 🐶 A+ Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Complete exterior renovation completed March 2023 Welcome to our home on North Captiva Island. Remote and undiscovered, ...
From $721 per night (USD)Expedia
- From $285 per night (USD)
VRBO
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 $285 per night (USD)VRBO
- From $191 per night (USD)
Expedia
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 $191 per night (USD)Expedia
- From $145 per night (USD)
VRBO
Island Home within the Pines; 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 $145 per night (USD)VRBO
- From $137 per night (USD)
Expedia
ISLAND TIME STARTS HERE! Stunning Fresh Water Pond Wildlife Views.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Time Begins when you cross over the Bridge!! The people of Pine Island are super friendly and not stressed out at ...
From $137 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 $60 per night (USD)
VRBO
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 ...
From $60 per night (USD)VRBO
- From $195 per night (USD)
VRBO
BEAUTIFUL GULF ACCESS HOME SAINT JAMES CITY CHERRY ESTATES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Immaculate saltwater canal Gulf access with no bridges minutes from open water. It doesn't get any better than this. Loo ...
From $195 per night (USD)VRBO
- From $590 per night (USD)
VRBO
Hidden Treasure - NEW near Beach-Pool-Tiki-Basketball- Club Use - Dock Available
- Bedrooms:
- 4
- 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 $590 per night (USD)VRBO
- From $695 per night (USD)
VRBO
NEW LISTING! SERENITY NOW~1 Min. To BEACH!-SCREENED-IN HEATED POOL-2 Carts-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 $695 per night (USD)VRBO
- From $333 per night (USD)
VRBO
***No Hurricane Ian Damage*** 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 $333 per night (USD)VRBO
- From $277 per night (USD)
VRBO
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 $277 per night (USD)VRBO
- From $149 per night (USD)
Expedia
A Florida Island, beautiful waterways, serenity!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“Something Fishy” is a newly remodeled, cozy, two bedroom, one bath mobile home on a quiet Florida island, with all the ...
From $149 per night (USD)Expedia
- From $250 per night (USD)
VRBO
My Sea Shack~ 1 minute to beach, SH Club access, golf cart
- Bedrooms:
- 4
- 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 $250 per night (USD)VRBO
- From $371 per night (USD)
VRBO
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 $371 per night (USD)VRBO