Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $1212 per night (USD)VRBO
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 $1212 per night (USD)VRBO
From $124 per night (USD)Expedia
Island Cottage-boat ramp at end of street! Walk to Jug Creek Marina!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom/one bath island cottage close to public boat ramp; fishing dock and marina. Down the street from kayak and p ...
From $124 per night (USD)Expedia
From $435 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 Due to recent Storm Damage boat lift is not operable at this time ...
From $435 per night (USD)VRBO
From $327 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 $327 per night (USD)Expedia
From $546 per night (USD)VRBO
Hear the Waves & See the Beach - 1 house to shore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 🌊 Amazing beach views & stunning sunsets 🏠 Professionally designed & extremely comfortable 🛥️Shared boat doc ...
From $546 per night (USD)VRBO
From $151 per night (USD)Expedia
Amazing Stay in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully renovated studio has everything you need for a fabulous stay in Matlacha. It is located on a quiet/peac ...
From $151 per night (USD)Expedia
From $516 per night (USD)VRBO
Paradise on Franzone HEATED POOL & OUTDOOR BAR
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Hurricane Ian Updated Description: Hurricane Ian hit Pine Islands very hard. The property has been getting som ...
From $516 per night (USD)VRBO
From $187 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 $187 per night (USD)Expedia
From $162 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 $162 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 $275 per night (USD)VRBO
Turtle House in matlacha on the water with spectacular sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This peacefull yet centrally located property has all the comforts you will need for the perfect getaway or extended sta ...
From $275 per night (USD)VRBO
From $1224 per night (USD)Expedia
Beachfront 3-Bedroom Oasis on North Captiva Island
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
🏠 Charming Interior Design & Coastal Furnishings 🏖️ Private Beach w/ Loungers 🌴 Spectacular Bay Views & Sunrises! ☀️ ...
From $1224 per night (USD)Expedia
From $177 per night (USD)VRBO
Bocilla Island Club Unit H-42
- Bedrooms:
- 3
- 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 $177 per night (USD)VRBO
From $223 per night (USD)Expedia
Matlacha Fishing cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This newly renovated 1940's Fishing Cottage is certain to catch your eye. Matlacha is a quiet village just on the way t ...
From $223 per night (USD)Expedia
From $281 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 $281 per night (USD)VRBO
From $327 per night (USD)Expedia
Beautiful three bedroom, two bath, large home has a pool and boat lift.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this stunning vacation rental, a spacious ground-level guest house with three bedrooms and two bathrooms. This ...
From $327 per night (USD)Expedia
From $390 per night (USD)VRBO
Spacious \"Crab Cakes\" Cottage on beautiful North Captiva Island,FL with GolfCart
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Crab Cakes Cottage on North Captiva Island, your perfect getaway destination! Nestled on a tranquil street, j ...
From $390 per night (USD)VRBO
From $287 per night (USD)Expedia
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 $287 per night (USD)Expedia
From $999 per night (USD)VRBO
~New! Gulf View! Private Pool! Beach, King beds~
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Isle Escape, an ocean view retreat where the Gulf’s beauty greets you the moment you step inside. The open-co ...
From $999 per night (USD)VRBO
From $260 per night (USD)Expedia
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 $260 per night (USD)Expedia
From $199 per night (USD)VRBO
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 $199 per night (USD)VRBO
From $219 per night (USD)Expedia
Off the Charts Inn - Standard Queen room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the sheer bliss of this spacious haven, complete with a fully equipped kitchen for your convenience. ...
From $219 per night (USD)Expedia
From $174 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 $174 per night (USD)VRBO
From $262 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 $262 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 $154 per night (USD)Expedia
Island Getaway, with boat ramp access nearby. You can park your boat on property
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relaxing is an understatement. Perfect island getaway from the city. It's good for retirees to families. Island culture ...
From $154 per night (USD)Expedia
From $609 per night (USD)VRBO
AWESOME NEW POOL HOME SPRAWLING OUTDR ENTERTAINING AREA/STEPS2 OCEAN/2CARTS/DOCK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
GORGEOUS ISLAND HOUSE RENTAL! BOOKING FOR VACATION RENTALS! TYPICALY 7 NIGHT RENTALS - WEEKENDS TO WEEKENDS during Prime ...
From $609 per night (USD)VRBO
From $141 per night (USD)Expedia
Pine Island Breeze where you can relax, swim, fish, see dolphins and manatees!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island Breeze, an island experience without leaving the country. Great place to relax, swim, fish, bike ride, explo ...
From $141 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 $162 per night (USD)Expedia
Incredible location. Waterfront unit in Matlacha with many amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Turnkey furnished - 1 bed, 1 bath with additional queen pullout sofa bed in the living room. Additional outside shower. ...
From $162 per night (USD)Expedia
From $343 per night (USD)VRBO
Waterfront Paradise in St. James City – 2BR/2BA with Pool, Dock & Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your perfect waterfront escape in beautiful St. James City! This spacious and newly updated 2-bedroom, 2-bath ...
From $343 per night (USD)VRBO
From $737 per night (USD)Expedia
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, Bikes+ 🏖️St ...
From $737 per night (USD)Expedia
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 $477 per night (USD)Expedia
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 $477 per night (USD)Expedia
From $156 per night (USD)VRBO
Summer Discounts! Gorgeous Four Winds Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy this beautiful newly remodeled 2 bedroom 2 bath condo with an amazing marina view! Four Winds Marina has The ...
From $156 per night (USD)VRBO
From $225 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 $225 per night (USD)Expedia
From $1115 per night (USD)VRBO
Flip Flops BEACH FRONT house and Sand Bar. \nMajestic panoramic views and sunsets
- Bedrooms:
- 3
- 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 $1115 per night (USD)VRBO
From $162 per night (USD)Expedia
Waterfront condo with easy water access to world class fishing and sightseeing.
- Bedrooms:
- 3
- 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 $162 per night (USD)Expedia
From $577 per night (USD)VRBO
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 $577 per night (USD)VRBO
From $209 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 $209 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 $229 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 $229 per night (USD)Expedia
From $304 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 $304 per night (USD)VRBO
From $887 per night (USD)Expedia
APRIL AND MAY SPECIAL 695/NIGHT! Private beach access, Heated Pool, Outdoor bar!
- 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 $887 per night (USD)Expedia
From $168 per night (USD)VRBO
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)VRBO
From $245 per night (USD)Expedia
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)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 $208 per night (USD)VRBO
Tangerine Dream Tropical Pool and Canal Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your slice of paradise in St. James City. This charming vacation rental offers the perfect blend of comfort, ...
From $208 per night (USD)VRBO
From $217 per night (USD)Expedia
3 bed 2 bath Gulf Access with boat lift in the heart of Saint James City.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This stunning 3-bedroom, 2-bathroom Gulf Access canal home, built in 2023, offers the perfect blend of modern living and ...
From $217 per night (USD)Expedia
From $122 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 $122 per night (USD)VRBO
From $224 per night (USD)Expedia
Welcome to Angler's Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our angler's paradise! This 2 Bedroom and 2 Bath retreat is tailored for the fishermen and fishing tournamen ...
From $224 per night (USD)Expedia
From $291 per night (USD)VRBO
Boaters Paradise in Matlacha Florida
- Bedrooms:
- 3
- 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 $227 per night (USD)VRBO
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
- Bedrooms:
- 3
- 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 $227 per night (USD)VRBO
From $535 per night (USD)Expedia
GORGEOUS ISLAND BEACH HOME 4 BRS/PRIVATE POOL/TIKI/360 ISLAND VIEWS/PET FRIENDLY
- Bedrooms:
- 3
- 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 $535 per night (USD)Expedia
From $83 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 $83 per night (USD)VRBO
From $497 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 $497 per night (USD)Expedia
Click For PricingVRBO
Turquoise Dolphin on Open Water/HeatedPool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: This home is on Matlacha Pass! Enjoy the gorgeous views of Matlacha Pass and watch the dolphins play from nearl ...
Click For PricingVRBO
From $256 per night (USD)Expedia
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 $256 per night (USD)Expedia
From $303 per night (USD)VRBO
Pool home with Dock - March booking special!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom pool home on deep Monroe Canal. Put your boat int he water at the house and avoid the ramp each day ...
From $303 per night (USD)VRBO
From $414 per night (USD)Expedia
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 ...
From $414 per night (USD)Expedia
From $515 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 $515 per night (USD)VRBO
From $199 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 $199 per night (USD)Expedia
From $155 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 $155 per night (USD)VRBO
From $337 per night (USD)Expedia
Gorgeous & Spacious 3/3.5, Incredible Water Views! Sleeps 9!
- Bedrooms:
- 4
- 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 $337 per night (USD)Expedia
From $326 per night (USD)VRBO
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 $326 per night (USD)VRBO
From $178 per night (USD)Expedia
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)Expedia
From $235 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 $235 per night (USD)VRBO
From $151 per night (USD)Expedia
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 $151 per night (USD)Expedia
From $174 per night (USD)VRBO
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)VRBO
From $412 per night (USD)Expedia
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)Expedia
From $262 per night (USD)VRBO
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)VRBO
From $658 per night (USD)Expedia
Treetop getaway on a secluded Island with gulf coast beaches
- Bedrooms:
- 2
- 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 $658 per night (USD)Expedia
From $562 per night (USD)VRBO
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 $562 per night (USD)VRBO
From $288 per night (USD)Expedia
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 $288 per night (USD)Expedia
From $288 per night (USD)VRBO
Cabana @ 2 Fish Inn Pool Side
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $288 per night (USD)VRBO
From $223 per night (USD)Expedia
Welcome to the Gecko House! 2/2 in St. James on Monroe Canal!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NEW PROPERTY! Charming 2 bedroom 2 bath on Monroe Canal! This property sits on a very active canal with direct water acc ...
From $223 per night (USD)Expedia
From $520 per night (USD)VRBO
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)VRBO
From $402 per night (USD)Expedia
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 $402 per night (USD)Expedia
From $396 per night (USD)VRBO
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 $396 per night (USD)VRBO
From $641 per night (USD)Expedia
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 $641 per night (USD)Expedia
From $303 per night (USD)VRBO
Best Kept Secret #SJC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Saint James City at this pleasant house. Family friendly spacious home, with 3 bedrooms and ...
From $303 per night (USD)VRBO
From $344 per night (USD)Expedia
Weekday Special Rates! Waterfront Oasis w/ Pool, & Dock- Sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Waterfront Retreat in St. James City, Florida – Sleeps 8 Escape to this beautifully finished vacation home in charming ...
From $344 per night (USD)Expedia
From $350 per night (USD)VRBO
The Jade House in Beautiful St James City
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Unwind in Saint James City at this lovely house. With 3 bedrooms including 2 queen beds and 1 bunk bed, this property of ...
From $350 per night (USD)VRBO
From $260 per night (USD)Expedia
Beautiful home with access to private beach, pool and hot tub.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Consider this townhome your home away from home while you visit Bokeelia. With 3 cozy bedrooms including a king, queen, ...
From $260 per night (USD)Expedia
From $233 per night (USD)VRBO
Matlacha Palms - Direct Gulf Access - Near Burnt S
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Matlacha Palms Matlacha Palms is a gorgeous, and cozy tree-bedrooms, 2 full bathroom vacation villa situated ...
From $233 per night (USD)VRBO
From $265 per night (USD)Expedia
The Monroe Lookout! 2/2 Pool Waterfront Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Waterfront Paradise in St. James City! Escape to your perfect island getaway at this stunning home nestled on the vibran ...
From $265 per night (USD)Expedia
From $325 per night (USD)VRBO
3-bedroom pool house on manatee-filled canal. BYOB: Bring your own boat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the beauty of Saint James City from this modern, updated 3-bedroom house in the Manatee Bay subdivision. Inside ...
From $325 per night (USD)VRBO
From $152 per night (USD)Expedia
Bocilla Island Club Unit C-13
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the charming Bocilla Island Club and discover the ultimate island getaway. This beautifully decorated vacation ...
From $152 per night (USD)Expedia
From $173 per night (USD)VRBO
Captains Harbor Island Hide Away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is one of Pine Island's most stunning and modernized two-bed and two-bath condo is waiting for you to live your bes ...
From $173 per night (USD)VRBO
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Furnished 2-bedroom condo in Bokeelia with, boat dock, pool, storage unit, etc.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Seasonal rental. Experience Bokeelia like a local in this 2-bedroom condo. This wonderful property features 1 king bed a ...
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Click For PricingVRBO
Saint James City Boaters Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A cozy cottage, newly renovated, nestled in on Dawson cannel off of Pine Island sound just 30 minutes by boat to Sanibel ...
Click For PricingVRBO
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 $106 per night (USD)Expedia
Lazy Dolphin Retreat\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WARNING ** This property may cause: calmness, relaxation, mindfulness and happiness! Relax at this unique and peaceful ...
From $106 per night (USD)Expedia
From $203 per night (USD)VRBO
Weekly Rental in Bokeelia! Captain's Cove Community!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 2-bedroom, 2-bathroom home in Bokeelia is an excellent choice for a seasonal rental! Situated in Captain's Cove, it ...
From $203 per night (USD)VRBO
From $208 per night (USD)Expedia
Spacious 3-Bedroom Bokeelia Oasis w/ Large Saltwater Pool & Outdoor Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise in Bokeelia, FL! Discover your own slice of paradise in this stunning 3-bedroom, 3 bathroom vacatio ...
From $208 per night (USD)Expedia
From $177 per night (USD)VRBO
3/2 Heated Pool Home on the Water, Monthly Rental Beautiful House!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 3-bedroom, 2-bathroom pool home located in the gated community of Pine Island Shores in St. James City. This be ...
From $177 per night (USD)VRBO
From $220 per night (USD)Expedia
Charming 3/2 Cottage in Bokeelia!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3/2 Cottage in Bokeelia! This cozy off-water property features 3 bedrooms, 2 bathrooms and a spacious living ro ...
From $220 per night (USD)Expedia