
Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $756 per night (USD)
VRBO
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)VRBO
- 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 $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)
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 $344 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
- Click For Pricing
Expedia
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 PricingExpedia
- From $1081 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 $1081 per night (USD)VRBO
- 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)
VRBO
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)VRBO
- 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)
Expedia
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)Expedia
- From $683 per night (USD)
VRBO
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)VRBO
- From $825 per night (USD)
Expedia
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)Expedia
- From $686 per night (USD)
VRBO
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)VRBO
- From $958 per night (USD)
Expedia
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)Expedia
- From $457 per night (USD)
VRBO
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)VRBO
- 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)
VRBO
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)VRBO
- 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)
Expedia
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)Expedia
- From $682 per night (USD)
VRBO
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)VRBO
- From $365 per night (USD)
Expedia
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)Expedia
- From $459 per night (USD)
VRBO
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)VRBO
- From $868 per night (USD)
Expedia
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)Expedia
- 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)
VRBO
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)VRBO
- From $614 per night (USD)
Expedia
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)Expedia
- 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 $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 $307 per night (USD)
Expedia
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)Expedia
- From $270 per night (USD)
VRBO
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)VRBO
- From $166 per night (USD)
Expedia
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)Expedia
- From $204 per night (USD)
VRBO
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)VRBO
- From $195 per night (USD)
Expedia
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)Expedia
- From $159 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- 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)
Expedia
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)Expedia
- 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 $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 $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 $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 $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
- From $397 per night (USD)
VRBO
THREE MASTER SUITES-POOL -WATERFRONT ON CORNER LOT - BOAT LIFT -OUTDOOR KITCHEN
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our beautiful newly remodeled home away from home is located in St. James City, Florida. It was just remodeled from the ...
From $397 per night (USD)VRBO
- From $445 per night (USD)
VRBO
GORGEOUS HUGE BEACH HOUSE W/ISLAND CLUB POOLS/BIKES/KAYAKS/VIEWS/2 GOLF CARTS+
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing the FANTASTIC "COASTAL SOUL"! This GORGEOUS, SPRAWLING, HIGH END Home is in a GREAT ISLAND LOCATION - SECO ...
From $445 per night (USD)VRBO
- From $876 per night (USD)
VRBO
Rum Cove: Private Heated Pool, Golf Cart, Docks, Airstrip & Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
You'll have the entire home to yourself and will only share it with other guests in your party. This Island Treasure ha ...
From $876 per night (USD)VRBO
- From $727 per night (USD)
Expedia
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Introducing Beach Paradise: A Luxurious Beachfront Retreat on North Captiva Island, Now Available for your next vacation ...
From $727 per night (USD)Expedia
- From $753 per night (USD)
VRBO
NORTH CAPTIVA PEARL -
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This newly completed, professionally designed multi-level, multi-deck home is located just 300 feet from the widest beac ...
From $753 per night (USD)VRBO
- From $379 per night (USD)
Expedia
Modern Renovation~2 Club Pools SHC&ICNC 👙 Kayaks 🛶 Bikes 🚲, Golf Cart 🚙 Dock
- 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 $379 per night (USD)Expedia
- From $273 per night (USD)
VRBO
Peaceful retreat. Fishing Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
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 $273 per night (USD)VRBO
- From $628 per night (USD)
VRBO
The Barrancas Barnacle! A Private Canal-Front Island Oasis w/ Dock, Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A one-of-a-kind Private Water-Front Bokeelia Property! Enjoy over an acre of gulf-access island living with this rare r ...
From $628 per night (USD)VRBO
- From $251 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 $251 per night (USD)VRBO
- From $937 per night (USD)
Expedia
NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Introducing Ocean Paradise: A Luxurious Beachfront Retreat on North Captiva Island, Now Available for your next vacation ...
From $937 per night (USD)Expedia
- From $296 per night (USD)
VRBO
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 $296 per night (USD)VRBO
- From $369 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 $369 per night (USD)Expedia
- From $196 per night (USD)
VRBO
2 bed/ 2.5 bath Waterfront Condo with 2 pools and great fishing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the ultimate comfort and relaxation at this beautifully remodeled garden front condo. With its inviting ambia ...
From $196 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Escape to SALTWATER&SUNSETS -Newly Remodeled-Pool & Club Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
🏝 As soon as you step on one of the BOAT FERRIES THAT DELIVERS you to the island let your cares melt away, enjoy the l ...
From $525 per night (USD)VRBO
- Click For Pricing
VRBO
Matlacha Island House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience the colorful charm and laid back style of Matlacha! This beautiful, bright and clean 2 bedroom, 2 bath ...
Click For PricingVRBO
- From $483 per night (USD)
Expedia
Holiday house Bokeelia for 1 - 8 persons with 3 bedrooms - Holiday house
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
ED Refnr. 3170641 This beautifully Tropical-appointed stilt house is located on Bokeelia with a view of Charlotte Harbo ...
From $483 per night (USD)Expedia
- From $374 per night (USD)
VRBO
3 Bed 2 Bath on Deep Canal 5 minutes to channel CLEAN & NICE. New boat hoist
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
No hurricane damage. This property is 100% ready to occupy. Nestled in Saint James City, Pine Island, Florida, this hous ...
From $374 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Cozy and warm 3-bedroom cottage with a pool in the island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the peace and tranquility of island living in this super clean cozy cottage that sits on a nearly 2/3-acre lot in ...
From $219 per night (USD)Expedia
- From $297 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 $297 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Tropical Island Oasis Full Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
4 bed • 2 bath • 1,600 sqft • 0.26 acres lot This lush tropical island oasis is the boating enthusiast's paradise: Priv ...
From $256 per night (USD)Expedia
- From $258 per night (USD)
VRBO
Waterside Cottage: Newly Renovated on canal w 26’ boat dock!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our peaceful little 5 Star rated island paradise nestled beneath sprawling oaks and scattered palms just minutes f ...
From $258 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Tarpon @ 2 Fish Inn with Pool and Dockage on Pine Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Tarpon is a one-bedroom suite at Two Fish Inn that offers a cozy retreat, featuring a queen bed in the bedroom, a pl ...
From $270 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Kayaks, Bicycles, Pool, Gulf Access: Endless Summer Feelings
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your secret haven of bliss in Southwest Cape Coral! This 3-bedroom, 2-bathroom dream home is your personal sa ...
From $324 per night (USD)VRBO
- From $211 per night (USD)
Expedia
2/2.5 Waterfront condo with pools and tennis courts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the enchanting Bocilla Island Club and experience the epitome of island living. This beautifully designed town ...
From $211 per night (USD)Expedia
- From $225 per night (USD)
VRBO
3/3 Home in Matlacha with Downstairs Suite! Incredible Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Check out this 2/2 in the heart of Matlacha! Two bedrooms upstairs with deck overlooking open water and 1 bedroom suite ...
From $225 per night (USD)VRBO
- From $318 per night (USD)
Expedia
Hidden Gem of South West Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your gulf access waterfront paradise in quaint Saint James City, Florida. A beautiful community to bask in the s ...
From $318 per night (USD)Expedia
- Click For Pricing
VRBO
PELICAN PERCH - Unobstructed Views, Private Pool, Golf Cart -Wow!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Pelican’s Perch – Location, Location, Location! This luxury home is just steps to the beach, unobstructed gulf views, a ...
Click For PricingVRBO
- From $326 per night (USD)
Expedia
The Clubhouse - Fish, Bike and Relax in this spacious Home with a Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Florida retreat. Nestled in a prime island location, our stylish well appointed home is ready for you to ...
From $326 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Dockside Breeze
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Fisherman’s getaway. You’ll treasure your peaceful time in St. James City with excellent fishing just minutes away. En ...
From $158 per night (USD)VRBO
- From $167 per night (USD)
VRBO
1 Mi to Boat Ramp: Bokeelia Home w/ Screened Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Seeking a coastal adventure filled with sunshine and good times? Look no further than this 2-bedroom, 1-bathroom vacatio ...
From $167 per night (USD)VRBO
- From $621 per night (USD)
VRBO
Newer construction designed to bring the outside in, short walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Breezy Palm is a two minute barefoot walk to the Island’s pristine white sand gulf beach. Come here to enjoy the tranqu ...
From $621 per night (USD)VRBO
- From $1230 per night (USD)
Expedia
Escape to CASA PALMA HIDEAWAY! 4BD/3BA, Pool, Outdoor Kitchen, boat slip & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This enchanting 4-bedroom, 3-bathroom retreat is a harmony of comfort and luxury, promising an unforgettable escape. On ...
From $1230 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Cozy and Private our island home on North Captiva is the perfect escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled at the conclusion of a tranquil lane lies Calliope Cottage, a snug and well-appointed bungalow offering optimal ...
From $324 per night (USD)VRBO
- From $811 per night (USD)
Expedia
Hear the Waves & See the Beach - 1 house to shore
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 🌊 Amazing beach views & stunning sunsets 🏠 Professionally designed & extremely comfortable 🛥️Shared boat doc ...
From $811 per night (USD)Expedia
- From $242 per night (USD)
VRBO
Off the charts Inn - Double Efficiency Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience comfort in our Double Efficiency, featuring two double beds, a living area, and a fully equipped kitchen. Unw ...
From $242 per night (USD)VRBO
- From $218 per night (USD)
Expedia
Off the Charts Inn King Efficiency
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the epitome of luxury with our King Efficiency suite. Indulge in the grandeur of a spacious king bed, a cozy ...
From $218 per night (USD)Expedia
- From $94 per night (USD)
VRBO
Island Getaway - Monthly Rental - 3 Queen Beds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy island life in this spacious and serene space. Gulf access and restaurants are in walking distance as well as boat ...
From $94 per night (USD)VRBO
- From $1293 per night (USD)
VRBO
Beachfront 3-Bedroom Oasis on North Captiva Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
🏠 Charming Interior Design & Coastal Furnishings 🏖️ Private Beach w/ Loungers 🌴 Spectacular Bay Views & Sunrises! ☀️ ...
From $1293 per night (USD)VRBO
- From $178 per night (USD)
VRBO
Bocilla Island Club Unit H-42
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Immerse yourself in the splendor of Charlotte Harbor with a stay in this exquisite waterfront condo. Prepare to be capti ...
From $178 per night (USD)VRBO
- From $361 per night (USD)
Expedia
A piece of heaven on earth, where island time begins.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for peace and tranquility? Come visit and get to know quaint Saint James City, FL. Beautiful sunset views right ...
From $361 per night (USD)Expedia
- From $437 per night (USD)
VRBO
Spacious \"Crab Cakes\" Cottage on N. Captiva Island,FL with GolfCart and Starlink
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Crab Cakes Cottage on North Captiva Island, your perfect getaway destination! Nestled on a tranquil street, j ...
From $437 per night (USD)VRBO
- From $1347 per night (USD)
Expedia
New Family Getaway • King Beds, Pool & Gulf Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Isle Escape, an ocean view retreat where the Gulf’s beauty greets you the moment you step inside with easy ac ...
From $1347 per night (USD)Expedia
- From $234 per night (USD)
VRBO
The Island House on Pine Island\nwith heat-pump heated most privacy pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to "The Island Home", a fully equipped private retreat nestled on Pine Island. Wake up to the serene ambiance of ...
From $234 per night (USD)VRBO
- From $260 per night (USD)
Expedia
Off the Charts Inn - King Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate luxury in our expansive King Suite! Indulge yourself in the grandeur of a king-sized bed, comple ...
From $260 per night (USD)Expedia




































































































