Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $337 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 $337 per night (USD)VRBO
From $328 per night (USD)Expedia
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 $328 per night (USD)Expedia
From $204 per night (USD)VRBO
Tranquility in St. James City! 2/2 Overlooking Mangroves!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover tranquility in this charming 2-bedroom, 2-bath home nestled among lush mangroves. Enjoy a fully stocked kitchen ...
From $204 per night (USD)VRBO
From $263 per night (USD)Expedia
Dream Vacation Pool and Waterfront Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
With its prime waterfront location, luxurious pool, and beautifully appointed living spaces, this 2-bedroom, 2-bathroom ...
From $263 per night (USD)Expedia
From $119 per night (USD)VRBO
Gulf Access Lake View Bokeelia Condo with Boat Slip.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walking, biking, boating, local dining and friendly people on Pine Island! This 2-bedroom condo is perfect for your esca ...
From $119 per night (USD)VRBO
From $194 per night (USD)Expedia
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 $194 per night (USD)Expedia
From $145 per night (USD)VRBO
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 $145 per night (USD)VRBO
From $520 per night (USD)Expedia
Luxurious waterfront home, pool, boat dock, filet station, private guest suite
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Coastal Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $520 per night (USD)Expedia
From $390 per night (USD)VRBO
Spacious, dog friendly home with pool, on waterway within minutes to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bowline Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $390 per night (USD)VRBO
From $387 per night (USD)Expedia
Gorgeous 3/2 Pool Home in St. James City, Incredible Water Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Brand new and gorgeous pool home in St. James City! This property offers 3 bedrooms, primary bedroom offering a king siz ...
From $387 per night (USD)Expedia
From $629 per night (USD)VRBO
North Captiva House on the Runway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "One Margarita" on North Captiva Island! This charming 3-bedroom, 3-bath beach house is perfect for families ...
From $629 per night (USD)VRBO
From $152 per night (USD)Expedia
2/2 Property in St. James City, Pet Friendly, Fenced in Yard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming 2/2 in St. James City with plenty of space to park a boat trailer and is pet friendly! Both rooms offering quee ...
From $152 per night (USD)Expedia
From $1492 per night (USD)VRBO
Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 🌊 Gulf Front Paradise 🏊♂️ Heated Private Saltwater Pool 🌅 Hot Tub Bliss: Enjoy stunning sunsets from the s ...
From $1492 per night (USD)VRBO
From $302 per night (USD)Expedia
Margaritaville! 3bd2ba house in Saint James City 2 mins to open water w13k lift.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming house in picturesque Saint James City. Close to everything on a quiet and quaint culdesac. With ...
From $302 per night (USD)Expedia
From $176 per night (USD)VRBO
Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a relaxing stay at this lovely 2-bedroom house in Matlacha, with boat lift. The house features 2 queen beds, 2 bat ...
From $176 per night (USD)VRBO
From $154 per night (USD)VRBO
Charming 2-bedroom house in quaint Matlacha with WiFi, AC, POOL and Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the beauty of Matlacha from this lovely 2-bedroom house. With a king bed and a Day bed that converts to a king ...
From $154 per night (USD)VRBO
From $258 per night (USD)VRBO
3-bedroom pool house in charming Bokeelia with AC, WiFi. Beautiful, peaceful,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Your Bokeelia adventure begins at this 3-bedroom pool house. With 1 king bed and 2 queen beds, this phenomenal property ...
From $258 per night (USD)VRBO
From $219 per night (USD)VRBO
Charming 2-bedroom house in delightful Matlacha with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the beauty of Matlacha from this lovely 2-bedroom house. With a king bed and a Day bed that converts to a king ...
From $219 per night (USD)VRBO
From $299 per night (USD)VRBO
Brand New Build, 3/3 Heart of Bokeelia! Boat Ramp Across the Street!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Cracker Jacks! Discover this stunning brand-new build located in the heart of beautiful Bokeelia! Perfectly d ...
From $299 per night (USD)VRBO
From $180 per night (USD)Expedia
Peaceful fishing Island paradise with boat lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our island getaway home is situated at the northwest end of Pine Island (off of FT Myers/ Cape Coral) in the community o ...
From $180 per night (USD)Expedia
From $713 per night (USD)VRBO
Silverseas Cottage-Luxury 3-bedroom, Steps to the Beach, Pool, 2 Carts, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
SILVERSEAS COTTAGE, The Perfect Beach Vacation Mere Steps From the Beach! Experience the ultimate beach vacation! Our ex ...
From $713 per night (USD)VRBO
From $571 per night (USD)Expedia
Pearl of the Island for 2, Cayo Costa
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This phenomenal beach house on Cayo Costa is the perfect home base for your trip. With 1 fabulous bedroom featuring a qu ...
From $571 per night (USD)Expedia
Click For PricingVRBO
Charlie's of Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Charlie's of Bokeelia on Pine Island – Your Perfect Home Island Escape This marvelous Bokeelia home offers e ...
Click For PricingVRBO
From $315 per night (USD)Expedia
Waterfront Bungalow in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the perfect getaway at this charming one-bedroom, one-bathroom waterfront bungalow. Nestled along the serene sh ...
From $315 per night (USD)Expedia
From $369 per night (USD)VRBO
3634 Bayview: 3 BR, 2.5 BA House in Saint James City, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream vacation destination, located in the highly sought-after waterfront community of Bayview Acres in ...
From $369 per night (USD)VRBO
From $100 per night (USD)Expedia
Charming Cottage in the Heart of Matlacha – Walk to Shops & Bay Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming Cottage in the Heart of Matlacha – Walk to Shops & Bay Views! Escape to paradise at this adorable coastal cott ...
From $100 per night (USD)Expedia
From $202 per night (USD)VRBO
Charming 2BR/2BA Pet-Friendly Home with Pool in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Charming 2BR/2BA Pet-Friendly Home with Pool in St. James City! Welcome to your perfect Florida getaway! This beautiful ...
From $202 per night (USD)VRBO
From $265 per night (USD)Expedia
Tangerine Dream, 2/2 Pool Home in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tangerine Dream! Escape to this charming 2-bedroom, 2-bath waterfront retreat in beautiful St. James City. Ea ...
From $265 per night (USD)Expedia
From $165 per night (USD)VRBO
Charming 3-bedroom mobile home with WiFi, AC in fantastic Saint James City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Unwind in Saint James City at this adorable mobile home. With 3 cozy bedrooms including 2 queen beds and 1 twin bed, gue ...
From $165 per night (USD)VRBO
From $346 per night (USD)VRBO
Blue Agave 2/2 Waterfront w/Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience laid-back Pine Island vibes at this newly renovated home! Relax with expansive waterfront views, a private po ...
From $346 per night (USD)VRBO
From $165 per night (USD)VRBO
\"Waterfront Gulf-Access Getaway – Fully Remodeled 2BR/2BA Vacation Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a peaceful stay at this 2-bedroom house in Saint James City. The cozy bedrooms feature 2 queen beds, perfect for a ...
From $165 per night (USD)VRBO
From $717 per night (USD)Expedia
SANDPIPER INN - TRUE BEACHFRONT Luxury; Pool/Hot tub & Golf cart NEW LISTING
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SANDPIPER INN – BEACHFRONT CONDO – POOL – GOLF CART Experience the ultimate beachfront getaway at this stunning beachfro ...
From $717 per night (USD)Expedia
From $198 per night (USD)VRBO
Charming 2-bedroom condo in a beautiful Bokeelia waterfront community!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the perfect blend of Florida’s timeless charm and modern peacefulness at our recently renovated Bokeelia waterf ...
From $198 per night (USD)VRBO
From $215 per night (USD)Expedia
Charming 2-bedroom waterfront townhome with WiFi, AC Hot Tub and dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Peaceful recently renovated home on Matlacha Island. This 2 bedroom 1 full bath home sits on a waterfront canal just a f ...
From $215 per night (USD)Expedia
From $585 per night (USD)VRBO
Dolphin House for 2, Cayo Costa Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 2
Unwind in Cayo Costa at this lovely house for 2. Including a queen bed, guests can relax in comfort. Enjoy the convenie ...
From $585 per night (USD)VRBO
From $259 per night (USD)Expedia
Paradise Point in St James City
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Charming 2Bd2Ba house in Saint James City heated pool, dock and lift. 1/2 Acre! This marvelous house is a gem waiting to ...
From $259 per night (USD)Expedia
From $815 per night (USD)VRBO
Villas in the Air – Elevated Island Living!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 🏊♂️ Heated pool on the main living level—no stairs for easy access! 🌅 Rooftop porch with stunning views of ...
From $815 per night (USD)VRBO
From $263 per night (USD)Expedia
Waterfront Paradise in Matlacha – 2BR/2.5BA | Adults Only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this stunning adult-only waterfront retreat in the heart of charming Matlacha. This beautifully appointed 2-be ...
From $263 per night (USD)Expedia
From $232 per night (USD)VRBO
Steps to Canal: St James City Home w/ Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beach Gear Provided | Walkable Boating Community | Laid-Back Living Secure your slice of paradise on Pine Island at thi ...
From $232 per night (USD)VRBO
From $258 per night (USD)Expedia
Outstanding 3 BR waterfront pool home in Matlacha Isles / kayaks/ fishing poles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully stocked and beautifully furnished 3 bedroom/ 2 bath waterfront home with heated pool, kayaks, and fishing poles. L ...
From $258 per night (USD)Expedia
From $766 per night (USD)VRBO
Matlacha Tiny Village
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $766 per night (USD)VRBO
From $261 per night (USD)Expedia
Beautiful 3/3 Island Retreat with Heated Pool, Dock & Private Boat Ramp.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to your perfect Pine Island getaway at this beautifully elevated 3-bedroom, 3-bath retreat, designed for relaxati ...
From $261 per night (USD)Expedia
From $807 per night (USD)VRBO
\" Here Comes The Fun\" Absolutely Magnificent! Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
HERE COMES THE FUN! Doo-d-Doo-Doo FUN FUN FUN HERE IT COMES! No detailed has been missed. This is truly a luxury home. ...
From $807 per night (USD)VRBO
Click For PricingExpedia
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 $344 per night (USD)VRBO
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 $344 per night (USD)VRBO
From $235 per night (USD)Expedia
Treasure Cove Serenity! 3/2 with Hot Tub!
- 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 $235 per night (USD)Expedia
From $194 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 $194 per night (USD)VRBO
From $233 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 $233 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 $278 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 $278 per night (USD)Expedia
From $262 per night (USD)VRBO
2/2 Waterfront home with pool and docking for a vessel.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A gorgeous 2-bedroom, 2-bathroom mobile home in the picturesque St. James City, FL. This charming retreat offers a perfe ...
From $262 per night (USD)VRBO
From $349 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 $349 per night (USD)Expedia
From $152 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 $152 per night (USD)VRBO
From $76 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 $76 per night (USD)Expedia
From $187 per night (USD)VRBO
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 $187 per night (USD)VRBO
From $254 per night (USD)Expedia
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 $254 per night (USD)Expedia
From $260 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 $260 per night (USD)VRBO
From $264 per night (USD)Expedia
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 $264 per night (USD)Expedia
From $367 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 $367 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 $167 per night (USD)VRBO
Waterfront condo with easy water access to world class fishing and sightseeing.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully appointed waterfront condo boasting two bedrooms and 2 1/2 baths in a quaint island atmosphere. Enjoy the fa ...
From $167 per night (USD)VRBO
From $206 per night (USD)Expedia
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 $206 per night (USD)Expedia
From $341 per night (USD)VRBO
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 $341 per night (USD)VRBO
From $213 per night (USD)Expedia
3/3 Amazing Heated Pool Home in St. James City!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom 3 bathroom home off water with an heated amazing pool! Recently upgraded including a beautiful kitch ...
From $213 per night (USD)Expedia
From $437 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 $437 per night (USD)VRBO
From $168 per night (USD)Expedia
Welcome to Island Vibes with a Modern Touch! Come enjoy Pine Island.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Relaxing property inside and out! Space for your family to enjoy the home and yard! Sitting out back during the day or n ...
From $168 per night (USD)Expedia
From $245 per night (USD)VRBO
Cozy Cottage on Direct Access Canal with Boat Lift
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Waterman is a newly remodeled 2 bedroom, 1 bath stilt bungalow. Located on the Monroe Canal, this home is perfect fo ...
From $245 per night (USD)VRBO
From $166 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 $166 per night (USD)Expedia
From $291 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 $291 per night (USD)VRBO
From $117 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 $117 per night (USD)Expedia
From $80 per night (USD)VRBO
Slice of Paradise on Pine Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in a peaceful, quiet, & private wooded area. Perfect for indulging in the laid-back island lifestyle with old Fl ...
From $80 per night (USD)VRBO
From $503 per night (USD)Expedia
The Secret Island Retreat Heated Pool Open Water
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a d ...
From $503 per night (USD)Expedia
From $178 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 $178 per night (USD)VRBO
From $234 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 $234 per night (USD)VRBO
From $149 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 $149 per night (USD)VRBO
From $174 per night (USD)Expedia
Captain`s Harbor Condo 2\/2 on the Water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy nature at its finest from the screened in porch of this beautiful 2 bedroom 2 bathroom Condo. This spacious condo ...
From $174 per night (USD)Expedia
From $412 per night (USD)VRBO
Gorgeous 3\/3 W\/ Downstairs Suite! Pool Home! Boat Lift!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Gorgeous 3/3 pool home with suite downstairs! This newly renovated home offers 2 bedrooms upstairs with a den that has a ...
From $412 per night (USD)VRBO
From $262 per night (USD)Expedia
Florida Style Villa by the Water with Pool, Dock, Gulf access!
- 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 $262 per night (USD)Expedia
From $608 per night (USD)VRBO
Treetop getaway on a secluded Island with gulf coast beaches
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to paradise! Your North Captiva Island stay includes The Island Club access to clubhouse pools, pool bar, hot t ...
From $608 per night (USD)VRBO
From $534 per night (USD)Expedia
Charming 2-bedroom house Welcome to Cay Cove Retreat, your serene getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Cay Cove Retreat, your serene getaway nestled at MATLACHA! This charming home offers the perfect blend of com ...
From $534 per night (USD)Expedia
From $289 per night (USD)VRBO
Snook/Sheephead @ 2 Fish Inn Waterside Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
The Snook/Sheephead @ the 2 Fish Inn offers an exceptional retreat for those seeking to explore the abundant charms of P ...
From $289 per night (USD)VRBO
From $289 per night (USD)Expedia
Cabana @ 2 Fish Inn Pool Side
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Are you searching for your slice of island paradise while on vacation? Look no further than the Cabana at the 2 Fish Inn ...
From $289 per night (USD)Expedia
From $643 per night (USD)VRBO
Tipsy Turtle: Private Pool, Optional NCI Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Are you familiar with what it takes to vacation on North Captiva Island, FL? (If you are, you're welcome to jump down to ...
From $643 per night (USD)VRBO
From $749 per night (USD)Expedia
Private beach oasis -- 2-minute walk to the ocean! w/ Golf Cart & Club Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The first thing you See or should we say "Sea" is the breathtaking Gulf of America from virtually everywhere from each ...
From $749 per night (USD)Expedia
From $311 per night (USD)VRBO
“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 $311 per night (USD)VRBO
From $283 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 $283 per night (USD)Expedia
From $292 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 150 feet of seawall. This Villa is a fi ...
From $292 per night (USD)VRBO
From $701 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 $701 per night (USD)VRBO
From $565 per night (USD)VRBO
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Find your ideal vacation home that fisherman and their wives love to bring their familys and vacation in Matlacha.Plenty ...
From $565 per night (USD)VRBO
From $264 per night (USD)Expedia
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 $264 per night (USD)Expedia
From $366 per night (USD)VRBO
Romantic beach home with golf cart 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 $366 per night (USD)VRBO
From $242 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 $242 per night (USD)Expedia
From $646 per night (USD)VRBO
The Salty Snook - LARGE BEACH HOME w/VIEWS!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
SPECIAL OPENING PRIME 4TH OF JULY WEEK AVAILABLE! JUNE 28TH or earlier to JUNE 5! Please inquire! - 7 night+ rental! ...
From $646 per night (USD)VRBO
From $259 per night (USD)Expedia
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bring the boat, kayaks, bikes and water toys. This high and dry Pine Island home on a canal has withstood all the storms ...
From $259 per night (USD)Expedia
From $299 per night (USD)VRBO
Game Room & Deck: Spacious Home in St James City
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Palm trees, warm weather, chic interior, oh my! Take that much-needed break from your day-to-day and travel to the islan ...
From $299 per night (USD)VRBO
From $166 per night (USD)Expedia
Island TreeTop House, Pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely cozy 2bed 1bath secluded house in quiet neighborhood. My home is very clean and uncluttered. Great for Two or t ...
From $166 per night (USD)Expedia
From $294 per night (USD)VRBO
Waterfront cottage in Matlacha, FL -<br>Unavailable at this time due to Hurr Ian.🌴
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our paradise cottage is in the cutest, artsiest, fishingest town, Matlacha FL, on Pine Island. Clean, updated and beauti ...
From $294 per night (USD)VRBO
From $453 per night (USD)Expedia
North Captiva Island- Ocean bay views and modern decor. Two new carts!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Bay - North Captiva Island Welcome to paradise! This townhome boasts the best of ocean bay views, wild beaches w ...
From $453 per night (USD)Expedia
From $282 per night (USD)VRBO
The Perfect Day in Matlacha! Direct Gulf Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Kick back & relax enjoying all that South West Florida has to offer!! Savor your morning coffee or evening wine on a bea ...
From $282 per night (USD)VRBO
From $351 per night (USD)Expedia
Relaxing Island View! Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a newer home with a spectacular view of the water. We are on a large bridged island that is very laid back and ...
From $351 per night (USD)Expedia