Calusa Land Trust and Nature Preserve of Pine Island Rentals
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 $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 $357 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 $357 per night (USD)VRBO
From $384 per night (USD)Expedia
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)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 $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 $348 per night (USD)VRBO
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)VRBO
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 $152 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 $152 per night (USD)VRBO
From $389 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 $389 per night (USD)Expedia
From $385 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 $385 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)VRBO
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)VRBO
From $658 per night (USD)Expedia
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 $658 per night (USD)Expedia
From $200 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 $200 per night (USD)VRBO
From $203 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 $203 per night (USD)Expedia
From $245 per night (USD)VRBO
Welcome to the Gecko House! 3/2 in St. James on Monroe Canal!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront Escape in St. James City, Canal Home with Boat Tie-Up Welcome to your perfect waterfront getaway in the hear ...
From $245 per night (USD)VRBO
From $543 per night (USD)Expedia
Luxurious waterfront home, pool, boat dock, fillet 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 $543 per night (USD)Expedia
From $446 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 $446 per night (USD)VRBO
From $641 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 $641 per night (USD)VRBO
From $312 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 $312 per night (USD)VRBO
From $443 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 $443 per night (USD)Expedia
From $260 per night (USD)VRBO
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)VRBO
From $341 per night (USD)Expedia
3-bedroom waterfront pool house in Manatee Bay. 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 $341 per night (USD)Expedia
From $193 per night (USD)VRBO
Bocilla Island Club Unit C-13
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the charming Bocilla Island Club and discover the ultimate island getaway. This beautifully decorated vacation ...
From $193 per night (USD)VRBO
From $173 per night (USD)Expedia
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)Expedia
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 $279 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 $279 per night (USD)Expedia
From $132 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 $132 per night (USD)VRBO
From $128 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 $128 per night (USD)Expedia
From $240 per night (USD)VRBO
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 $240 per night (USD)VRBO
Click For PricingExpedia
Beachfront! 2 Houses - Sleeps up to 16!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: 🌊 Gulf Front! 🏠2 professionally decorated homes 🛋️Sleeps 16 comfortably 🛥️ Shared boat dock - ask about ava ...
Click For PricingExpedia
From $525 per night (USD)VRBO
Emerald Palms Island Escape - 4 BR Tropical Oasis on Pine Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A spectacular variety of tropical plants, flowers & seashell paths surround this custom built 2 story cedar siding villa ...
From $525 per night (USD)VRBO
From $220 per night (USD)VRBO
Charming Pet-Friendly Bungalow... \n2 bed/2 bath Near Jug Creek & Boat Ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to tranquility on Pine Island! Unplug and unwind at this charming 2-bedroom, 2-bath vacation retreat in the hear ...
From $220 per night (USD)VRBO
From $177 per night (USD)VRBO
Bocilla Island Club H-43
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the heart of serenity, the fantastic Island Condo of H43 at Boccilla Island Club beckons you with its unparal ...
From $177 per night (USD)VRBO
From $271 per night (USD)Expedia
3BR Waterfront townhome Matlacha with hot tub, boat dock WiFi, bikes and kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located in Matlacha, enjoy what this 3-bedroom 2 full bath townhome has to offer. With 1 queen bed, 1 king bed, and 1 tw ...
From $271 per night (USD)Expedia
From $446 per night (USD)VRBO
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Captain's Quarters – A Tropical Paradise on North Captiva Island Welcome to Captain's Quarters, your private island ret ...
From $446 per night (USD)VRBO
From $119 per night (USD)VRBO
Crab Cove Inn. 3/2 Direct Gulf Access with 50 ft sea wall.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our 3-bedroom, 2-bathroom canal front home with a fully equipped kitchen. Enjoy dinner on the deck or in the d ...
From $119 per night (USD)VRBO
From $1566 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 $1566 per night (USD)VRBO
From $326 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 $326 per night (USD)Expedia
From $995 per night (USD)VRBO
WHITE PELICAN WATCH- Unobstructed views, on beach, heated pool, slip NEW LISTING
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Your Dream Unobstructed Beachfront Getaway! Experience the ultimate in island living with our stunning 4-be ...
From $995 per night (USD)VRBO
From $256 per night (USD)VRBO
WATERFRONT, POOL, BOAT LIFT, WALKING DISTANCE TO RESTAURANTS, 2 BED/2 BATH
- 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 $256 per night (USD)VRBO
From $258 per night (USD)VRBO
Bokeelia Oasis! Heated Pool, Sleeps 12!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Escape to this stunning tropical retreat in Bokeelia, where relaxation meets luxury! This beautifully designed home feat ...
From $258 per night (USD)VRBO
From $734 per night (USD)Expedia
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 $734 per night (USD)Expedia
From $351 per night (USD)VRBO
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Its all about the WOW!! Your Matlacha adventure begins at this chic 3-bedroom 3 full bath house. This home has been rebu ...
From $351 per night (USD)VRBO
From $758 per night (USD)Expedia
Shellabration - Ocean Views and Family Fun!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: 🏡 Spacious luxury home – ensuite baths in every bedroom 🌊 Breathtaking ocean & preserve views 🏖 Beach-ready! ...
From $758 per night (USD)Expedia
From $1060 per night (USD)VRBO
4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Island Time Beach House – Your Ultimate Getaway on North Captiva Island! Welcome to Island Time Beach House, a newly re ...
From $1060 per night (USD)VRBO
From $244 per night (USD)Expedia
Sandpiper Oasis St James
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
to spend with. Set in a prime location, it offers modern amenities and comfortable accommodations for a memorable vacati ...
From $244 per night (USD)Expedia
From $841 per night (USD)VRBO
Beautiful Island Beach Home, Private Pool, Steps from the Best Beach, Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Sunny By You Beach House has EVERYTHING you need for a perfect North Captiva Island getaway! Welcome to Paradise on Nort ...
From $841 per night (USD)VRBO
From $415 per night (USD)Expedia
3-bedroom house in charming Saint James City with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming house in Saint James City is a serene retreat for guests seeking a pleasant getaway. With 3 cozy bedrooms ...
From $415 per night (USD)Expedia
From $182 per night (USD)VRBO
ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is laid back Old Florida wher ...
From $182 per night (USD)VRBO
From $1106 per night (USD)Expedia
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Paraíso – A Luxury Beachfront Escape with Private Dock & Resort-Style Amenities. Welcome to Paraíso, your exclusive lux ...
From $1106 per night (USD)Expedia
From $415 per night (USD)VRBO
The Boat House! Home with 2 Living Spaces in Bokeelia, Sleeps 11!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Spacious Waterfront Retreat in Bokeelia – Perfect for Families & Groups! Discover your ideal island getaway at this bea ...
From $415 per night (USD)VRBO
From $139 per night (USD)VRBO
Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to your slice of coastal heaven just minutes from Sanibel, Fort Myers & Captiva! This beautifully decorated 2-be ...
From $139 per night (USD)VRBO
From $206 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 $206 per night (USD)VRBO
From $1211 per night (USD)Expedia
TURTLE & PIPER SHORES–Double Your Pleasure–6 BR BEACHFRONT - POOL, 2 GOLF CARTS
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
TURTLE & PIPER SHORES – DOUBLE YOUR PLEASURE – BEACHFRONT 6 BEDROOMS SIDE BY SIDE DUPLEX WITH PRIVATE POOL/HOT TUB COMBO ...
From $1211 per night (USD)Expedia
From $736 per night (USD)VRBO
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 $736 per night (USD)VRBO
From $223 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 $223 per night (USD)Expedia
From $397 per night (USD)VRBO
3634 Bayview Avenue (Paradise): 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 $397 per night (USD)VRBO
From $204 per night (USD)Expedia
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 $204 per night (USD)Expedia
From $162 per night (USD)VRBO
St James City brand new 3-bedroom home with WiFi, AC and boat lift
- 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 $162 per night (USD)VRBO
From $950 per night (USD)Expedia
Villas in the Air – Elevated Island Living!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 🏊♂️ Heated pool on the main level—no stairs for easy access! 🛋️ Thoughtfully designed with elevated interio ...
From $950 per night (USD)Expedia
From $355 per night (USD)VRBO
Beach house with Lake View, Boat Slip, Golf Cart, Pickleball and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME Quiet, safe, peaceful, golf cart community with Beautiful powder white undiscovered sandy beaches, and cryst ...
From $355 per night (USD)VRBO
From $198 per night (USD)Expedia
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)Expedia
From $175 per night (USD)VRBO
Matlacha Tiny Village-Iguana
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Ti ...
From $175 per night (USD)VRBO
From $199 per night (USD)Expedia
Matlacha Tiny Village - Flamingo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $199 per night (USD)Expedia
From $207 per night (USD)VRBO
Matlacha Tiny Village - Dolphin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $207 per night (USD)VRBO
From $292 per night (USD)Expedia
\"Charming 3-Bedroom House One Canal from Bay with Boat Lift in Saint James City
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Your cozy getaway in Saint James City awaits at this charming 3-bedroom home. Complete with a washing machine, iron, hai ...
From $292 per night (USD)Expedia
From $313 per night (USD)VRBO
Waterfront 2BR/2BA Getaway w/Pool In Sunny Saint James City, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect island getaway in beautiful St. James City, located on the southern tip of Pine Island, Florida. ...
From $313 per night (USD)VRBO
From $174 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 $174 per night (USD)Expedia
From $289 per night (USD)VRBO
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 $289 per night (USD)VRBO
From $622 per night (USD)Expedia
Waterfront with Private Dock!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: 🛥️ Private dock for boating, fishing, or relaxing 🚣♂️ Kayak launch next door — kayaks included! 🌅 Stunning ...
From $622 per night (USD)Expedia
From $818 per night (USD)VRBO
Casa Blanca on the Gulf: Elegant Beachfront Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 🏖️ Beachfront paradise, bordered by untouched nature on both sides— serene, and truly private 🖼️ Coastal-chic ...
From $818 per night (USD)VRBO
From $1827 per night (USD)Expedia
Private Island Oasis! Gulf Views + Pool & Carts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 🌴 Total privacy in a lush garden retreat 🌅 Front-row sunsets with unobstructed gulf views 🌿 Scenic trails th ...
From $1827 per night (USD)Expedia
From $339 per night (USD)VRBO
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 $339 per night (USD)VRBO
From $240 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 $240 per night (USD)VRBO
From $276 per night (USD)VRBO
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 $276 per night (USD)VRBO
From $526 per night (USD)Expedia
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 $526 per night (USD)Expedia
From $669 per night (USD)VRBO
Charming 2-bedroom house in pleasant Saint James City with AC, WiFi, Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in one of the sweetest parts of Saint James City, this delightful house offers 2 cozy bedrooms - one with a king ...
From $669 per night (USD)VRBO
From $172 per night (USD)Expedia
Tiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Bokeelia, walking distance from the Pineland marina, this 4-bedroom house offers a peaceful elevated retreat ...
From $172 per night (USD)Expedia
From $184 per night (USD)VRBO
The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Golden Flamingo – Old Florida Charm with Modern Comforts Welcome to The Golden Flamingo, your peaceful escape in th ...
From $184 per night (USD)VRBO
From $143 per night (USD)VRBO
Island Treasure! Brand new on an olde Florida island in the Gulf.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Welcome to Island Treasure.** Nestled on a dirt, jungly road, this brand-new 3 bedroom, 2 bath oasis is your gateway ...
From $143 per night (USD)VRBO
From $261 per night (USD)VRBO
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)VRBO
From $510 per night (USD)Expedia
CAPTAIN JACKS -LOOK NO FURTHER - THIS IS TRUE LUXURY! 6 P GOLF CART; POOL; SLIP
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the coastal charm of North Captiva Island with this beautiful townhome. From the living area and gue ...
From $510 per night (USD)Expedia
From $172 per night (USD)VRBO
The Flamingo at Sandpiper 2 bed 2 bath waterfront location with dock and lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A stunning 2-bedroom, 2-bathroom coastal retreat where you can park your boat right behind your house! Enjoy the ultimat ...
From $172 per night (USD)VRBO
From $202 per night (USD)Expedia
Waterfront getaway direct Gulf access, open living area two bed and two baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to Your Perfect Waterfront Getaway in St. James City, Pine Island! Experience the ultimate coastal retreat at th ...
From $202 per night (USD)Expedia
From $327 per night (USD)VRBO
Stilted Waterfront Escape with Dock, Lift, Fire Pit & Game Room
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 level vacation rental on stilts is a perfect getaway. The upper level boasts two bedrooms (both with ensuite bath ...
From $327 per night (USD)VRBO
From $228 per night (USD)VRBO
Sunset Retreat on Matlacha. Charming 2/1 house on Matlacha Pass.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our cozy 2-bedroom, 1-bathroom waterfront retreat in the heart of Matlacha, Florida! Nestled on the serene wa ...
From $228 per night (USD)VRBO