
Calusa Land Trust and Nature Preserve of Pine Island Rentals
- 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 $381 per night (USD)
VRBO
House on Matlacha Pass with pool, hot tub, kayak dock & 12k lb boat lift!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our spacious open concept home with a great outdoor living space that opens up fully to a lanai overlooking the Ma ...
From $381 per night (USD)VRBO
- From $413 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 $413 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Island Getaway Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3Bedroom 2 bath remodeled pool home in St James City Triple lot with plenty of privacy with huge 13' deep pool with a wa ...
From $339 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $241 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 $241 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 $760 per night (USD)
VRBO
LVCC Villa Green Adventure
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This spectacular Vacation Villa will take you on a green adventure, in more than one way. Firstly, when thinking of the ...
From $760 per night (USD)VRBO
- From $274 per night (USD)
VRBO
Deluxe King Suite w/Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Deluxe King Suite is the epitome of comfort and sophistication, offering a private escape with distinct features. En ...
From $274 per night (USD)VRBO
- From $542 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 $542 per night (USD)VRBO
- From $191 per night (USD)
VRBO
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 $191 per night (USD)VRBO
- From $242 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 $242 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 $1181 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 $1181 per night (USD)Expedia
- From $344 per night (USD)
VRBO
Spring Summer Specials-close to restaurants, boat ramp & marina,2 paddle-boards
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
15% off 5 days, 20% off 7+ days, 30% 30 days Your gulf access waterfront paradise awaits! Modern home with beautiful can ...
From $344 per night (USD)VRBO
- From $293 per night (USD)
Expedia
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 $293 per night (USD)Expedia
- From $727 per night (USD)
VRBO
Waterfront home with private pool, dock, patio, balconies, & bikes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Maison de Sirens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $727 per night (USD)VRBO
- From $487 per night (USD)
Expedia
VRCC Villa Paradisio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
website: www.vr-capecoral.com Villa Paradisio - Located less than 500 yards from the Stonis Park, Restaurants, Tennis C ...
From $487 per night (USD)Expedia
- From $193 per night (USD)
VRBO
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 $193 per night (USD)VRBO
- From $123 per night (USD)
VRBO
Studio Snapper Room in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy a great time right here in one of the best places on earth! We guarantee the most beautiful sunset of Fl ...
From $123 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Studio Snapper Room in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy a great time right here in one of the best places on earth! We guarantee the most beautiful sunset of Fl ...
From $124 per night (USD)VRBO
- From $258 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 $258 per night (USD)Expedia
- From $382 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 $382 per night (USD)VRBO
- From $437 per night (USD)
Expedia
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars. NCIC member
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Incredible newly renovated 3 bedroom home with gulf views! Open layout with exceptional outdoor spaces including huge fr ...
From $437 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Gulf Hidden Jewel POOL Kayak bikes fish from dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Time! Gulf access waterfront oasis. New pool! Two bedrooms, 1 full bath, full size kitchen and washer/ ...
From $156 per night (USD)VRBO
- From $265 per night (USD)
Expedia
Tropical Oasis Pool Kayak Bikes fish from dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Island Time! Gulf access waterfront home. New Pool Great for family or groups sharing. 3 bedrooms, 2 full ba ...
From $265 per night (USD)Expedia
- From $127 per night (USD)
VRBO
Sunrise In Paradise POOL Kayak bikes fish from dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Island Time! Gulf access waterfront oasis. New pool ! 1 bedroom, 1 full bath with bath tub, 1 kitchen, washer ...
From $127 per night (USD)VRBO
- From $309 per night (USD)
Expedia
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 $309 per night (USD)Expedia
- From $1377 per night (USD)
VRBO
BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 17
VVISIT OUR WEBSITE: WWW.BEAUTYANDTHEBEACHNORTHCAPTIVA.COM BEAUTY AND THE BEACH – 5 Bedrooms with 3 Master Suites | Slee ...
From $1377 per night (USD)VRBO
- From $373 per night (USD)
Expedia
Blue Pearl-close to beach, screened porch, club, courtesy golf cart for 4.
- 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 $373 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Secluded Island Beach Home - Starcut Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Starcut Cottage, our dream home on our favorite island. When we stayed in this home in the spring of 2022 we ...
From $500 per night (USD)VRBO
- From $123 per night (USD)
Expedia
Studio Snapper Room in Matlacha/Fisherman's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
<p>Located on the waterfront, this welcoming vacation home lets you experience it all in Matlacha. Lovegrove Gallery & G ...
From $123 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Seaside Villa Destin - Single home with privat pool in the heart of Pine island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our Seaside Villa Destin is idyllically located on Pine Island, which is situated in front of Cape Coral. Especially for ...
From $350 per night (USD)VRBO
- From $999 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 $999 per night (USD)Expedia
- From $293 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 $293 per night (USD)VRBO
- From $756 per night (USD)
Expedia
Steps from the beach! Spacious island retreat with pool, grill, and space for 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Coquina Beach House, your home-away-from-home on private North Captiva Island! Just a 4-minute walk from the ...
From $756 per night (USD)Expedia
- Click For Pricing
VRBO
Heart of Matlacha Studio-remodeled! NEW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
It's rare to find a place that's both historic and one-of-a-kind. It’s even rarer to find a place that is historic, uniq ...
Click For PricingVRBO
- Click For Pricing
Expedia
Old world Florida luxury waterfront sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This luxury unit on the open waters of the Matlacha Aquatic Preserve is part of a double unit and is now ready for guest ...
Click For PricingExpedia
- From $185 per night (USD)
VRBO
Pine Island Paradise - Saltwater Canal 2 bed/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for your own piece of island paradise? This beautifully decorated spacious 2 bedroom, 2 bathroom home in St. Jam ...
From $185 per night (USD)VRBO
- 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 $344 per night (USD)
VRBO
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 $344 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- Click For Pricing
VRBO
Your own little bit of paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautifule trailer 1 bedroom plus sofa bed so you have planty of room for 4 people . A few steps to canal that leads to ...
Click For PricingVRBO
- From $1081 per night (USD)
Expedia
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 $1081 per night (USD)Expedia
- From $240 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 $240 per night (USD)VRBO
- From $446 per night (USD)
Expedia
New! Modern 3 Bed Townhome on North Captiva Island w/Beachfront views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahoy, land-ho! Gorgeous getaway destination ahead! Come visit La Casa Delphine: an elegant 3-bedroom waterfront haven, t ...
From $446 per night (USD)Expedia
- From $259 per night (USD)
VRBO
Unique Charlotte Harbor experience on a comfortable Schucker 436 trawler.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boaters Only at this time. I want to welcome boaters to an experience of a lifetime! You must have a boat that you can ...
From $259 per night (USD)VRBO
- From $386 per night (USD)
VRBO
The Bokeelia Boathouse, waterfront, Boat Dock, Pine Island, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise awaits you at our recently renovated island get away home. Located on the water in Bokeelia on Pine Island we ...
From $386 per night (USD)VRBO
- From $628 per night (USD)
VRBO
Beach's Edge, On the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful home is right on the Florida sugar sand beach, which is often uninhabited except by wading birds, ghost c ...
From $628 per night (USD)VRBO
- From $683 per night (USD)
Expedia
Perfect Placement, A beautiful beachfront home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home (sleeps 6 adults and 4 children) is extremely close to the ocean and a Florida sugar sand beach whic ...
From $683 per night (USD)Expedia
- From $825 per night (USD)
VRBO
New luxury pool home, 2 min to beach, 360 water views, club available
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 19
Overview of the property: • Sublime is a new, stunning 3,200 square foot, 7-bedroom, 6-bathroom, luxury beach home w/ s ...
From $825 per night (USD)VRBO
- From $686 per night (USD)
Expedia
Big on the Beach House, Oceanfront with Stunning views!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
This oceanfront 6 bedroom home is located on North Captiva Island and can accommodate up to 16 people. It comes with th ...
From $686 per night (USD)Expedia
- From $958 per night (USD)
VRBO
Reel Laxing: Private Pool, Hammocks & Games
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Reel Laxing, your ultimate retreat on North Captiva Island. This spacious 4-bedroom home offers a blend of re ...
From $958 per night (USD)VRBO
- From $457 per night (USD)
Expedia
Cozy Island home, pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This cozy home sits right in the middle of the island and is located in a cul de sac street making it very quiet and pri ...
From $457 per night (USD)Expedia
- From $109 per night (USD)
VRBO
Lovely 1-Bedroom Vacation Home with Pool & Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax with the whole family at this peaceful place to stay. High speed WI-FI, completely furnished, fully equipped kitch ...
From $109 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Private Heated Pool Home - Pine Island Getaway - One-Level, 3-bedroom, 2-bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private Pool Retreat in Bokeelia | Pine Island’s Hidden Gem -3BR/2BA beautifully remodeled home with private heated poo ...
From $339 per night (USD)VRBO
- From $676 per night (USD)
VRBO
Oceanfront Luxury Home with Secluded Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Sandcastle is a completely updated beachfront home that has been owned by a single family for over 40 years, and i ...
From $676 per night (USD)VRBO
- From $732 per night (USD)
Expedia
Newly Remodeled 4 Bedroom House w Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nama-Stay is located on a barrier island in southwest Florida. In fact, the only way to get to the island by boat or pri ...
From $732 per night (USD)Expedia
- From $499 per night (USD)
VRBO
OCEAN WAVES -LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE BRAND NEW "OCEAN WAVES" CALENDAR IS OPEN TO BOOK YOUR DATES TODAY! ONE OF THE BEST BEACH FRONT LOCATIONS ON NORTH ...
From $499 per night (USD)VRBO
- From $162 per night (USD)
VRBO
Bokeelia Charming Island House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your getaway home- a newly remodeled spacious 3 beds 2 bath house, the left side unit of a duplex. Quiet and ...
From $162 per night (USD)VRBO
- From $471 per night (USD)
VRBO
Butterfly Beach on North Captiva Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
"Experience Island Paradise at Butterfly Beach: Your North Captiva Oasis Escape to a world of luxury and tranquility at ...
From $471 per night (USD)VRBO
- From $682 per night (USD)
Expedia
Special:10% Discount! Book 2026 with private pool, elevator, ocean view!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Turtle Cove on Upper Captiva Island is here to help you provide an experience for your loved ones. Book your stay today ...
From $682 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Pools, Kayaks, Tennis, Golf Cart & Both Island Clubs Included w/Boat Dock Option
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on North Captiva Island, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pool ...
From $365 per night (USD)VRBO
- From $459 per night (USD)
Expedia
Amazing sunsets, Fishing from the dock, Large lanai & Pool - Villa Boa Vista - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Boa Vista – Lake Views, Heated Pool & Gulf Access Paradise! Welcome to Villa Boa Vista, your dream escape in sunny ...
From $459 per night (USD)Expedia
- From $868 per night (USD)
VRBO
Spectacular Sunsets. Private multilevel designer home with heated pool and spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Multilevel Designer Home with plenty of room for family. Multiple living areas and plenty of outside areas to enjoy. T ...
From $868 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Beautiful pool home on canal with 45-foot boat dock. 10 minutes to Gulf by boat.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island is the No. 1 Tarpon fishing spot in the world. Many islands to go to for shelling, fishing, dining. After yo ...
From $323 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Florida style home is for guests who want to relax and unwind. It is located on a quiet street and the refreshing ...
From $145 per night (USD)VRBO
- From $476 per night (USD)
Expedia
Exclusive Deal: Luxury Water Jewel featuring Private Boat & Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Jewel of the Water - this spacious home boasts 4 bedrooms, 2 of which have ensuite baths. Dock and lift with 24ft Swe ...
From $476 per night (USD)Expedia
- From $614 per night (USD)
VRBO
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SANTA CLARA BEACH HOUSE is a NEW LISTING and is a luxurious, newly furnished 3 bedroom harbor front rental property loca ...
From $614 per night (USD)VRBO
- From $193 per night (USD)
VRBO
Pine Island Breeze/Bokeelia 1 Bdrm 1 bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A perfect place to be as close to people or as far away as you like. Pine Island is 20 minutes to busier areas of Fort ...
From $193 per night (USD)VRBO
- From $241 per night (USD)
VRBO
6 Person 1-Bedroom Condo with Waterview Balcony - Lighthouse - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated one-bedroom condo with a balcony, situated on the beautiful Gulf coast! With the ability ...
From $241 per night (USD)VRBO
- From $204 per night (USD)
Expedia
4 Person 1 Bedroom Condo with Waterview Patio - Snapper - Welcome to our newly renovated one-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $204 per night (USD)Expedia
- From $307 per night (USD)
VRBO
6 Person 2-Bedroom Condo with Patio - Redfish - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated two-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep six gu ...
From $307 per night (USD)VRBO
- From $423 per night (USD)
Expedia
8 Person 3-Bedroom Condo with Private Patio - Mermaid - Welcome to our newly renovated, luxurious and spacious three-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated three-bedroom condo situated on the beautiful Gulf coast! With the ability to sleep eight ...
From $423 per night (USD)Expedia
- From $307 per night (USD)
VRBO
8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated two-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the a ...
From $307 per night (USD)VRBO
- From $270 per night (USD)
Expedia
6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated one-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the a ...
From $270 per night (USD)Expedia
- From $166 per night (USD)
VRBO
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $166 per night (USD)VRBO
- From $204 per night (USD)
Expedia
4 Person 1 Bedroom Condo with Waterview Balcony Fisherman Cabin - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $204 per night (USD)Expedia
- From $195 per night (USD)
VRBO
4 Person 1 Bedroom Condo with Waterview Balcony- Dolphin - 4 Person 1 Bedroom Condo with Waterview Balcony - Dolphin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our stunning one-bedroom condo room with a balcony! Imagine waking up to breathtaking views every morning and ...
From $195 per night (USD)VRBO
- From $159 per night (USD)
Expedia
2 Person Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $159 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 $329 per night (USD)
VRBO
Beautiful waterfront home, new refinished heated pool, boat dock bikes & kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and thank you for looking into Casa High Tide! Owners have recently made lots of upgrades to this wonderful prope ...
From $329 per night (USD)VRBO
- From $868 per night (USD)
VRBO
Solitude North Captiva, Carts, Dock, Private Pool, Club, Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
**Welcome to Solitude – Your North Captiva Island Escape** Solitude offers a truly unique North Captiva experience, ble ...
From $868 per night (USD)VRBO
- From $273 per night (USD)
VRBO
The Hook Oar House - Waterfront Retreat with Private Boat Lifts - 2B/2B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to The Hook Oar House, your perfect waterfront retreat for fishing, kayaking, and boating in St. James City, Flor ...
From $273 per night (USD)VRBO
- From $137 per night (USD)
VRBO
Waterfront Effeciency Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy efficiency apartment attached to the "Hook Oar House" has everything you need for a comfortable and relaxing ...
From $137 per night (USD)VRBO
- From $237 per night (USD)
Expedia
GORGEOUS RENTAL! Paradise In Old Time Florida at \"The Dew Drop Ian\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very secluded on a dead-end road. Fabulous Stilt Cottage where the breeze keeps you cool all day in the many open air si ...
From $237 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Corner Condo in Blue Crab Key, Bokeelia!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Immaculate waterfront condo with one of the best views around. Direct access to Matlacha Pass and some of the worlds bes ...
From $175 per night (USD)VRBO
- From $507 per night (USD)
VRBO
GORGEOUS HOME WITH HEATED POOL ON WATER AND COMMUNITY BOAT RAMP
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come and enjoy Island Time in this beautiful 3 bedroom home with an amazing heated pool. This home has a large master be ...
From $507 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Linesider Hideaway Beach House - North Captiva Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to North Captiva Island and our home Linesider Hideaway. North Captiva is a barrier island to the west of the ma ...
From $574 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Dog-friendly waterfront home with heated pool, lanai, central AC, & W/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beverly's Tarpon Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $254 per night (USD)Expedia
- From $522 per night (USD)
VRBO
Boater's Dream Nestled On a Wide Gulf Access Canal - Bokeelia Breeze
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your ultimate waterfront getaway at Bokeelia Breeze! This stunning vacation rental sits on a wide, Gulf-access ...
From $522 per night (USD)VRBO
- From $285 per night (USD)
Expedia
2/2 Home in Bokeelia, Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pi ...
From $285 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Quiet, clean & comfy 2 bed-2bath with 8000lb boat lift and large screened lanai
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute, clean and comfy 2 bed, 2 full bath mobile home in Saint James City, Florida on a quiet canal with 8000 pound boatl ...
From $195 per night (USD)VRBO
- From $710 per night (USD)
VRBO
Luxury island home with a private pool, game area, golf carts, club access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hakuna Matata – Worry-Free Island Living on North Captiva Escape to Hakuna Matata, a bright, beautiful 3-bedroom, 2-bat ...
From $710 per night (USD)VRBO
- From $793 per night (USD)
VRBO
Private Island Luxury * Pool * Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 🏠 Exquisite interior design & curated coastal furnishings 🏖️ Stroll to beach: chairs, umbrellas, wagon provid ...
From $793 per night (USD)VRBO
- From $362 per night (USD)
Expedia
3/2 Heated Pool Home With Endless Water Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
TThis 3 bedroom 2.5 bath heated pool home is the perfect spot for relaxation. Bring your boat or enjoying the two kayaks ...
From $362 per night (USD)Expedia
- From $512 per night (USD)
VRBO
New Listing!! Dolphin Watch-3 Bedroom Beach Front on North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Our house is located directly on the beach! We are located on the northeast side of the island (the bay side just south ...
From $512 per night (USD)VRBO
- From $145 per night (USD)
Expedia
Relaxing Pine Island Center Nature Lovers Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, location! Wonderful Non smoking Guest home in a quiet, peaceful neighborhood located in convenient Pine Island ...
From $145 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Beautiful waterfront home with pool/spa, boat lift, kayaks and kayak launch!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Island home with direct access to Matlacha Pass. A 2-story property equipped with a pool and spa, high-speed internet, s ...
From $495 per night (USD)VRBO
- From $462 per night (USD)
Expedia
Island Cottage in Quaint Matlacha Florida. Amazing island life is a click away…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy, 3 bedroom bungalow cottage is nestled on a peninsula located in the heart of Matlacha Florida. With the conve ...
From $462 per night (USD)Expedia




































































































