Calusa Land Trust and Nature Preserve of Pine Island Rentals
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 $309 per night (USD)VRBO
Private home on the canal with dock, screened pool, patio, AC, & W/D - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rock N' Reel Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $309 per night (USD)VRBO
From $434 per night (USD)Expedia
Casa Florida 🌴 waterfront home with boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
☞ Wifi ☞ Free boat ramp ☞ Walk Score 70 (Walk to cafes, dining, shopping etc.) ☞ 50” Smart TV ☞ Private patio w/ seatin ...
From $434 per night (USD)Expedia
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 $224 per night (USD)Expedia
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 $224 per night (USD)Expedia
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 $208 per night (USD)Expedia
The Palm Tree House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
beautiful 3 bedroom 2 bath home in a 55 plus community. Situated on 1/3 of an acre and backing onto a palm tree farm, ...
From $208 per night (USD)Expedia
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 $145 per night (USD)VRBO
2/2 Cherry Estates Vacation Perfection
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***POOL COMING SOON*** Your next getaway awaits at the beautiful Cherry Estates in St. James City, FL. Our inviting 2-b ...
From $145 per night (USD)VRBO
From $296 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 $296 per night (USD)Expedia
From $369 per night (USD)VRBO
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)VRBO
From $196 per night (USD)Expedia
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)Expedia
From $76 per night (USD)VRBO
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 $76 per night (USD)VRBO
From $197 per night (USD)Expedia
2/2.5 condo with docking available for your boat and pools for soaking
- Bedrooms:
- 2
- 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 $197 per night (USD)Expedia
From $313 per night (USD)VRBO
Terrific vacation home on quiet Clipper Lane 2/2 pool home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this remarkable vacation home nestled on peaceful Clipper Lane, just off Sanibel Blvd., in the charming town o ...
From $313 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
From $279 per night (USD)VRBO
3 bedroom 2 bath pool home in quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a charming 3-bedroom, 2-bathroom canal home, offering a delightful pool and dock. This tastefully decorated re ...
From $279 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $360 per night (USD)VRBO
BEAUTIFUL WATERFRONT HOME WITH SALTWATER POOL AND CANAL ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The relaxed atmosphere at this beautiful home is perfect for vacationers who want to get away from everyday stress and w ...
From $360 per night (USD)VRBO
From $157 per night (USD)Expedia
Beautiful waterfront condo with gulf access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bocilla Island Club! Just listed and AVAILABLE JANUARY, FEB AND/OR MARCH 2024. This turnkey waterfront townho ...
From $157 per night (USD)Expedia
From $483 per night (USD)VRBO
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)VRBO
From $374 per night (USD)Expedia
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)Expedia
From $311 per night (USD)VRBO
Dog-friendly, canal-front getaway with a dock, screened lanai, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lavender Life Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $311 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 $261 per night (USD)Expedia
Matlacha Cottage 2/2 remodeled& sunsets!\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Matlacha Cottages, a serene and unique open water getaway, perfect for solo travelers or couples. This ma ...
From $261 per night (USD)Expedia
From $256 per night (USD)VRBO
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)VRBO
From $212 per night (USD)Expedia
Condo in Four Winds! 2/2 Incredible Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This condo offers the finest in island getaway accommodations. Beautiful waterfront 2 bedroom/2 bath unit with abundant ...
From $212 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 $215 per night (USD)VRBO
Studio#1-Back Bay Sunsets in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take it easy at this unique and tranquil open water getaway - perfect for the solo traveler or a couple. Oversized close ...
From $215 per night (USD)VRBO
From $328 per night (USD)Expedia
Beautiful 5/3 Pool, Saltwater Cove, Sleeps 10!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury 5-Bedroom Home on Private Saltwater Cove with Stunning Views! Discover your dream waterfront retreat! This exquis ...
From $328 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 PricingVRBO
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 $324 per night (USD)Expedia
Flamingo Bay Cottage (3-Bedroom) - Pets Allowed by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Flamingo Bay Cottage, your idyllic retreat nestled in the heart of paradise in Saint James City, Florida. T ...
From $324 per night (USD)Expedia
From $326 per night (USD)VRBO
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)VRBO
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 $299 per night (USD)Expedia
3/2 Pool Home in St. James, Gorgeous Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom two home with amazing canal views. This home includes a heated pool, boat lift, 3 bedrooms, large outside ...
From $299 per night (USD)Expedia
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 $398 per night (USD)VRBO
Stunning Waterfront Home with Southeast Bay Frontage - Villa Cuquita
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Cuquita • St. James City Vacation Rental MILITARY DISCOUNT: 10% off for primary guests on Military Active Duty or ...
From $398 per night (USD)VRBO
From $324 per night (USD)Expedia
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)Expedia
From $811 per night (USD)VRBO
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)VRBO
From $242 per night (USD)Expedia
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)Expedia
From $218 per night (USD)VRBO
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)VRBO
From $94 per night (USD)Expedia
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)Expedia
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)Expedia
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)Expedia
From $361 per night (USD)VRBO
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)VRBO
From $437 per night (USD)Expedia
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)Expedia
From $252 per night (USD)VRBO
St James City,Watch sunsets,Dolphins, manatees on Canal while on Spa, kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our spectacular waterfront view deck with direct gulf access, along with various water-based activities with two k ...
From $252 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
From $231 per night (USD)VRBO
Off the Charts Inn - Queen Double Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate comfort and luxury in our expansive Queen double bed room! Immerse yourself in the sheer bliss o ...
From $231 per night (USD)VRBO
From $304 per night (USD)Expedia
Pet friendly 3 bedroom, 2 bath pool home with direct access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this pet-friendly home, eagerly awaiting your arrival. With three bedrooms and two full baths, it provides a ...
From $304 per night (USD)Expedia
From $206 per night (USD)VRBO
Cozy home in Matlacha on the water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
comfy 2 bedroom 2 bathroom house in matlacha. House has beautiful kitchen and bathrooms. This home also is on the water ...
From $206 per night (USD)VRBO
From $540 per night (USD)VRBO
AWESOME POOL HOME SPRAWLING OUTDR ENTERTAINING/STEPS2 OCEAN/2CARTS/CLUB & TENNIS
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
GORGEOUS ISLAND HOUSE RENTAL! BOOKING FOR VACATION RENTALS! TYPICALY 7 NIGHT RENTALS - WEEKENDS TO WEEKENDS during Prime ...
From $540 per night (USD)VRBO
From $476 per night (USD)VRBO
Luxury Island Escape @ Palm Tree Villa: Private Rooftop Deck & Saltwater Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Palm Tree Villa, a luxurious retreat nestled on Pine Island’s serene Gulf Coast in Southwest Florida. Spannin ...
From $476 per night (USD)VRBO
From $189 per night (USD)Expedia
All new, incredible location! Waterfront unit in Matlacha with many amenities.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Professional, full renovation completed Aug 2025. 1 bed, 1 bath with additional queen pullout sofa bed in the living roo ...
From $189 per night (USD)Expedia
From $948 per night (USD)VRBO
Lookout Escape: Private Island Luxury*Gulf Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower 🏖️Steps from ...
From $948 per night (USD)VRBO
From $282 per night (USD)VRBO
Beautiful Island Sanctuary with Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our upscale, spacious 3 br/2 ba home, located in a quiet neighborhood Bokeelia. Here, you and your family can ...
From $282 per night (USD)VRBO
From $635 per night (USD)VRBO
Turtle Escape: Pool, Beach & Fun!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 🍹 Outdoor Oasis: Pool, Bar, Games, TV & Shower 🐚 Beach Access: A Short Leisurely Stroll Away 🛥️ Shared boat ...
From $635 per night (USD)VRBO
From $215 per night (USD)Expedia
Priceless Waterfront Escape in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Discover island living at our newly-remodeled waterfront escape in Matlacha on a deep water canal with a private dock (l ...
From $215 per night (USD)Expedia
From $1078 per night (USD)VRBO
Flip Flops BEACH FRONT house and Sand Bar. \nMajestic panoramic views and sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful 2 story beach front house with ground floor Patio and Sand Bar. Home is located on the exclusive North Captiva ...
From $1078 per night (USD)VRBO
From $709 per night (USD)Expedia
SEA TURTLE COVE-BEACHFRONT LUXURY-3 BR/2BA Pool/Hot tub combo - Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Sea Turtle Cove – Beautiful Sunsets - North Captiva Island Our POOL/HOT Tub combo is complete - check out the new pictu ...
From $709 per night (USD)Expedia
From $211 per night (USD)VRBO
Summer Special! Waterfront 3/2 Pine Island!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3/2 in located in the heart of St. James City! Nestled on a quiet corner, on a large lot offering so much ...
From $211 per night (USD)VRBO
From $357 per night (USD)Expedia
Villa Papaya in St James city !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your island getaway in the charming community of St. James City! This vacation rental home offers the perfect ...
From $357 per night (USD)Expedia
From $384 per night (USD)VRBO
Do you like to fish, relax, chill and enjoy nature? Do we have the place for you
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sonny Palms. This Direct Gulf Access Home has been completely remodeled in fall of 2021. This home offers: 3 ...
From $384 per night (USD)VRBO
From $903 per night (USD)Expedia
Private Beach Access Steps Away, Pool, Outdoor Bar, 2 Golf Carts, 360 Views.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
5 Star Property. We are located on the Northern tip of North Captiva Island, with lots of privacy away from the crowds ...
From $903 per night (USD)Expedia
From $296 per night (USD)VRBO
Pine Island canal home with boat access to Gulf.\n\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your morning coffee with spectacular sunrises looking down the canal. Typical Florida landscaping with palm trees, ...
From $296 per night (USD)VRBO
From $397 per night (USD)Expedia
Casita Salida del Sol-North Captiva Island Waterfront townhouse w/dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "Casita Salida del Sol", your private sanctuary nestled on the pristine shores of North Captiva Island, Flori ...
From $397 per night (USD)Expedia
From $137 per night (USD)VRBO
3/2 Stilt Home in the Heart of Saint James City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very desirable stilt vacation rental in a wonderfully friendly and quiet neighborhood. Old Saint James City has a conve ...
From $137 per night (USD)VRBO
From $188 per night (USD)Expedia
Welcome to Angler's Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our angler's paradise! This 2 Bedroom and 2 Bath retreat is tailored for the fishermen and fishing tournamen ...
From $188 per night (USD)Expedia
From $285 per night (USD)VRBO
Boaters Paradise in Matlacha Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This peaceful yet centrally located cottage within walking distance to town has an open floor plan with master suite and ...
From $285 per night (USD)VRBO
From $144 per night (USD)Expedia
Paradise on the water w/ a pool & great fishing!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A fishing and boating paradise! ~You're on Island Time~ A beautiful, professionally decorated waterfront condo in St. ...
From $144 per night (USD)Expedia
From $197 per night (USD)VRBO
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come enjoy island time year-round and soak up the laid-back island vibes from this newly renovated, cozy bungalow situat ...
From $197 per night (USD)VRBO
From $552 per night (USD)VRBO
GORGEOUS ISLAND BEACH HOME 4 BRS/PRIVATE POOL/TIKI/360 ISLAND VIEWS/PET FRIENDLY
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FANTASTIC OPPORTUNITY! GREAT RATES! BOOK NOW! Thank you for your interest in Paloma Beach House! Book us today for your ...
From $552 per night (USD)VRBO
From $305 per night (USD)VRBO
Fishing inshore, offshore, with easy access to Charlotte Harbor and Gulf.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated cottage with three bedrooms located on the tip of Pine Island. Go boating in Charlotte Harbor with qu ...
From $305 per night (USD)VRBO
From $348 per night (USD)Expedia
Pool home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom pool home on deep Monroe Canal. Put your boat in the water at the house and avoid the ramp each day ...
From $348 per night (USD)Expedia
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Colorful waterfront home with private W/D, WiFi, and dock access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Castaway Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
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From $520 per night (USD)VRBO
BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"BEACH DAYZ" HAS JUST OPENED UP! SPECIAL RATES FOR THIS NEWLY LISTED BEACH FRONT PROPERTY!" SIMPLY ONE OF THE BEST BEAC ...
From $520 per night (USD)VRBO
From $228 per night (USD)VRBO
4/2 Off Water Property in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4/2 Off Water Home in St. James City! This 4 bedroom 2 bathroom homes offers a ton of space for the entire family with a ...
From $228 per night (USD)VRBO
From $152 per night (USD)Expedia
Charming Waterfront Cottage on peaceful Matlacha! FULL RENOVATION DECEMBER 2024
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a fisherman’s paradise in picturesque Matlacha. This charming vacation rental offers a cozy retreat for guests ...
From $152 per night (USD)Expedia
From $389 per night (USD)VRBO
Gorgeous & Spacious 3/3.5, Incredible Water Views! Sleeps 9!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Incredible 3 bedroom 3.5 bath home with endless water views! This brand new renovated home offers so much space for the ...
From $389 per night (USD)VRBO
From $385 per night (USD)Expedia
Antigua Cay Retreat is a stylish home with pool on deep water canal in Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably right on the water in Bokeelia at this amazing 3 bedroom 2 bath fully renovated custom home. This lovel ...
From $385 per night (USD)Expedia
From $200 per night (USD)VRBO
Charming 2-bedroom house in beautiful Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our charming retreat in Bokeelia, FL. Nestled on Pine Island, this cozy getaway offers a serene escape with b ...
From $200 per night (USD)VRBO
From $238 per night (USD)VRBO
Charming waterfront home in Saint James City on Main Canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Island Blues Charming Home! Welcome to our tranquil Island Blues home with beautiful canal views and direct access to ...
From $238 per night (USD)VRBO
From $203 per night (USD)VRBO
Relax on Island Time In This 2 Bed / 1 Bath Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Saint James City, FL, and unwind in this charming 2-bedroom home near Tropical Point Park. Enjoy an open kitch ...
From $203 per night (USD)VRBO
From $299 per night (USD)Expedia
Florida Style Villa by the Water with heated Pool, Dock, Gulf access! Kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You love the water... then this is your place to be! The villa has been completly renovated in 2024! Start kayaking or b ...
From $299 per night (USD)Expedia