Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $701 per night (USD)VRBO
Oceanfront beach home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Robin’s Beach Nest is located on some of the most prized beachfront property on the entire island, featuring some of the ...
From $701 per night (USD)VRBO
From $80 per night (USD)VRBO
Spacious Getaway, 1 to 4 for Easy Going Nature Lovers on beautiful Pine Island.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Comfy home w pretty garden on historic Pine Island. Nearby fishing, kayaking, birding, good eats, tennis. Visit pristine ...
From $80 per night (USD)VRBO
From $1139 per night (USD)VRBO
Parrothead's Paradise - 4 BR House - Private Boat Dock & Brand New Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Parrothead's Paradise! Located on the secluded barrier island of Upper Captiva, Parrothead’s Paradise is a l ...
From $1139 per night (USD)VRBO
From $1166 per night (USD)Expedia
BLUE MANGO -- Tropical Seclusion Steps from the Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
"HURRICANE HELENE/MILTON UPDATE: We sustained only MINOR damage, mostly to the exterior landscape and are READY ...
From $1166 per night (USD)Expedia
From $153 per night (USD)VRBO
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 $153 per night (USD)VRBO
From $294 per night (USD)Expedia
Waterfront cottage in Matlacha, FL -<br>Unavailable at this time due to Hurr Ian.🌴
- Bedrooms:
- 2
- 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)Expedia
From $3000 per night (USD)VRBO
Beachfront🌊4 KING suites&bunk room🛏️Pet Friendly🐾
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 12
🛥️New offering: Free boat dock 👙GULF FRONT 180° amazing beach views 🏠Professionally designed/decorated 🛌🏽Westin Hea ...
From $3000 per night (USD)VRBO
From $450 per night (USD)VRBO
Calling Waters-Gulf access w\/dock, pool and HT.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This canal front home has a heated pool, private dock capable of hosting a 25-foot boat, barbecue grill, patio space, sc ...
From $450 per night (USD)VRBO
From $197 per night (USD)VRBO
Paradise at Serenity Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled away in a quiet community on Pine Island’s NE side, this home is an angler’s or kayaker’s paradise! The home is ...
From $197 per night (USD)VRBO
From $1254 per night (USD)Expedia
Cayo Costa Paradise Found
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 8
Private beach, Air conditioned, sleeps 6 with additional space for two on the 1st floor apartment, (requires additional ...
From $1254 per night (USD)Expedia
From $131 per night (USD)VRBO
Reopened in November 2023!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $131 per night (USD)VRBO
From $499 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 $499 per night (USD)Expedia
From $825 per night (USD)VRBO
The Salty Conch - Luxury Just Steps To The Beach with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Book your stay at the beautiful, new to the rental market, island house, just a short golf cart ride to the beach! The ...
From $825 per night (USD)VRBO
From $386 per night (USD)VRBO
The Perfect Day in Matlacha! Direct Gulf Access!
- Bedrooms:
- 3
- 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 $386 per night (USD)VRBO
From $148 per night (USD)VRBO
Island Paradise, waterfront location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Quiet island living, with quick access to pine island sound from your dock. Great kyaking, fishing and 16 miles of safe ...
From $148 per night (USD)VRBO
From $370 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 $370 per night (USD)Expedia
From $338 per night (USD)VRBO
LUXURY ISLAND TOWNHME\/CLUB w\/POOL! 4 BRs, 2 KINGS, KAYAKS, & BOAT DOCKAGE AVAIL!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
*** The FABULOUS “DRAGONFLY POINT” is a LUXURY ISLAND TOWNHOME located on North Captiva Island! A Remote Barrier Island ...
From $338 per night (USD)VRBO
From $706 per night (USD)VRBO
NEW!!! THE BIRDS & THE BEACH - 4\/3 Sleeps 12, HUGE Private Pool, 2 GOLF CARTS\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
SPACIOUS 4 BR. 3 BATH - sleeps 12 in beds, 2 Golf Carts, PRIVATE HEATED POOL , SPECIAL PRICING FOR SUMMER BOOKINGS Bac ...
From $706 per night (USD)VRBO
From $252 per night (USD)VRBO
Beautiful Bokeelia!!!! Fishing dream!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bokeelia property within walking distance to Bokeelia Fishing pier and captain con’s restaurant. Studio with king size b ...
From $252 per night (USD)VRBO
From $296 per night (USD)VRBO
Fisherman & Kayaker's Delight! 3 BR, 2 BA Waterfront Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This inviting 3-bedroom, 2-bathroom stilt home (stairs required to entrance) is an idyllic retreat for your Southwest Fl ...
From $296 per night (USD)VRBO
From $152 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $152 per night (USD)VRBO
From $229 per night (USD)VRBO
Bocilla Island Club Condo, Boat Dock, 400 foot Private Pier, 2 Pools, Tennis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
16709 Bocilla Palms Dr., Bokeelia Our condo also includes a private dock capable of holding a boat up to 36ft, 400 foot ...
From $229 per night (USD)VRBO
From $534 per night (USD)VRBO
Gulf getaway! Boat dock, HEATED saltwater pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to @TheGulfGetaway an incredible canal-side home built to make memories. You'll enjoy the comfort of a fully equ ...
From $534 per night (USD)VRBO
From $145 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $145 per night (USD)VRBO
From $180 per night (USD)VRBO
Serenity abounds. Astounding sunsets, beautiful waters & perfect weather.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy easy living in a relaxed golf course community ....bike trails, nature walks, kayaking, boating, fishing, golf and ...
From $180 per night (USD)VRBO
From $248 per night (USD)VRBO
Sunset Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Matlacha, it’s a water sports paradise! World class fishing, boating, kayaking, beautiful sunrises and sunsets! See natu ...
From $248 per night (USD)VRBO
From $705 per night (USD)VRBO
Butterfly Breeze on North Captiva Island, Ask About Special Fall and Low Occupancy Rates
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to your own slice of island paradise at Butterfly Breeze – a luxurious retreat just moments away from the beach o ...
From $705 per night (USD)VRBO
From $320 per night (USD)Expedia
North Captiva waterfront Townhome with dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sea Turtle townhouse is a beautifully decorated three bedroom townhouse located in Safety Harbor Club on the unspoil ...
From $320 per night (USD)Expedia
From $464 per night (USD)VRBO
Fun'n Sun-Charming 3 BR\/3 baths waterfront villa- pool, spa, dock, fishing poles
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This property is a boater’s and fisherman’s delight. Fully stocked, and beautifully furnished 3-bedroom 3-bathroom water ...
From $464 per night (USD)VRBO
From $280 per night (USD)VRBO
Quick Gulf Access. This Home has it all.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This home has it all: Direct Five Minute Access, Boat Dock with Use Of Lift Optional. Quiet Neighborhood, Restaurants an ...
From $280 per night (USD)VRBO
From $792 per night (USD)VRBO
The Silverseas Cottage - Charming, Immaculate with Private Pool - 2 Golf Carts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to the Silverseas Cottage, an immaculate and charming 3-bedroom, 2-bathroom vacation home on remote North Captiv ...
From $792 per night (USD)VRBO
From $2022 per night (USD)Expedia
Captiva Beach Sunset ~Gulf front, pool, NCIC, 4 & 6 seater carts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 17
Captiva Beach Sunset - 5 BR/4.5 BA - Sleeps 12 in beds- Beachfront with Private Pool Queen size air mattress is availabl ...
From $2022 per night (USD)Expedia
From $138 per night (USD)VRBO
Mermaid Waterfront Hideaway Great fishing, kayaking, boat lift available too!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Florida home on the water. Located in quaint little village of St. James City, this property is away from the t ...
From $138 per night (USD)VRBO
From $227 per night (USD)Expedia
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Come enjoy a beautiful gulf access condo in Bocilla Island Club, at the northern tip of Pine Island. Enjoy your morning ...
From $227 per night (USD)Expedia
From $759 per night (USD)VRBO
LUNAR TIDES - 3 BR\/2 BA - Your dream vacation spot! Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your dream vacation to an island paradise is just a few clicks away! Lunar Tides is located on the barrier island of No ...
From $759 per night (USD)VRBO
From $155 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $155 per night (USD)VRBO
From $153 per night (USD)VRBO
Private Hideaway in Pine Island community Pool and Marina a few steps away.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is my personal dream getaway I’m newly sharing with avid travelers looking to escape their hectic lives and live in ...
From $153 per night (USD)VRBO
From $688 per night (USD)VRBO
Prime Spot on Pristine North Captiva Island. Private Elevated Pool & Deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to North Captiva Island! A short, ferry ride separates you from reality, for your tropical paradise vacation. A ...
From $688 per night (USD)VRBO
From $311 per night (USD)VRBO
Saint James hidden gem. 3\/2 canal front home with 3 kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your gulf access waterfront paradise is waiting in quaint Saint James City. 3 Kayaks and 2 bikes for your use to explor ...
From $311 per night (USD)VRBO
From $498 per night (USD)Expedia
Matlacha 3-bedroom vacation home. Lg Dock.Hot tub, Boatlift, walk to restaurants
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Find your ideal vacation home that fisherman and their wives love to bring their familys and vacation in Matlacha.Plenty ...
From $498 per night (USD)Expedia
From $295 per night (USD)VRBO
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 $295 per night (USD)VRBO
From $234 per night (USD)VRBO
Walking, biking, boating, local dining and friendly people on Pine Island!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This immaculate, well-kept condo has 2 bedrooms with in-suite bathrooms, two balconies, 2 pools and tennis courts. Resta ...
From $234 per night (USD)VRBO
From $497 per night (USD)VRBO
Romantic beach home with golf cart kayaks and bikes. 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 $497 per night (USD)VRBO
From $447 per night (USD)VRBO
Southwest Florida Home Pool Fishing Biking Hiking Sun & Fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty and charm of Pine Island, Florida, with our spacious three-bedroom vacation rental, complete with a ...
From $447 per night (USD)VRBO
From $484 per night (USD)VRBO
LaySea 8 - Across from Nature Preserve and steps to the best beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LaySea 8 is an octagonal house with a spectacular 360 degree view of the Gulf of Mexico, Nature Preserve and Pine Island ...
From $484 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 $1597 per night (USD)VRBO
Steps from the beach, gulf views, on the airstrip and Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you are searching for an island vacation that is different from all others, then search no more for you have stumbled ...
From $1597 per night (USD)VRBO
From $534 per night (USD)VRBO
Island Oasis\/Hidden Beach House-Private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This traditional, Florida-style island cottage is situated less than 200 yards down a private path to the Gulf of Mexic ...
From $534 per night (USD)VRBO
From $522 per night (USD)VRBO
Newly Renovated Island Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise, no cars, no crowds. Located in the Castaway Key subdivision on the island, this charming cottage ha ...
From $522 per night (USD)VRBO
From $747 per night (USD)Expedia
Private beach oasis -- 2-minute walk to the ocean! w\/ Golf Cart & Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The first thing you See or should we say "Sea" is the breathtaking Gulf of Mexico from virtually everywhere from each r ...
From $747 per night (USD)Expedia
From $885 per night (USD)VRBO
BEACH FRONT with the best sunsets on the island!!!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Newly remodeled, ON THE BEACH! OCEAN FRONT HOME ON PRISTINE SANDY WHITE BEACHES Spectacular views, best sunsets! WE ar ...
From $885 per night (USD)VRBO
From $504 per night (USD)VRBO
“Viva Captiva” - Vibrant beachfront home, 150 steps to the Gulf of Mexico
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
North Captiva Island remains a relatively undiscovered paradise, offering the laidback lifestyle that Florida used to be ...
From $504 per night (USD)VRBO
From $581 per night (USD)VRBO
The Salty Snook
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unique Gulf Front and View Home : Private Dockage for up to 30 Foot Boat available...Perfect Florida Fishing Get Away. ...
From $581 per night (USD)VRBO
From $403 per night (USD)VRBO
Spectacular Nature! Waterfront! Prime Tarpon Fishing! Bring Boat, 2 Free Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Taking reservations for 2024 & 2025. No hurricane damage. Fishing enthusiasts, kayakers, bird watchers, nature lovers... ...
From $403 per night (USD)VRBO
From $1285 per night (USD)VRBO
At the Beach: Heated Pool, Golf Cart, Club Access, Winter Dates Avail! Book Now
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Gulf Swells & Sea Shells – your ultimate oceanfront haven! Completely renovated, this stunning 5-bedroom, 5-b ...
From $1285 per night (USD)VRBO
From $481 per night (USD)VRBO
Rockstar Beach House North Captiva Island 25’ private boat dock NCIC pools Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** UPDATE ** Rockstar has many recent upgrades including a new Reverse osmosis system in the kitchen, added Super fast S ...
From $481 per night (USD)VRBO
From $144 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $144 per night (USD)VRBO
From $494 per night (USD)Expedia
“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 $494 per night (USD)Expedia
From $131 per night (USD)VRBO
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great holiday days right here in one of the best places on earth! We guarantee the most beautiful sunset ...
From $131 per night (USD)VRBO
From $878 per night (USD)Expedia
Tipsy Turtle: Pvt, swim up bar, golf carts, beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
(In recent news...The fall of 2024 was a challenging one for North Captiva Island due to hurricanes passing through. Ti ...
From $878 per night (USD)Expedia
From $151 per night (USD)VRBO
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $151 per night (USD)VRBO
From $311 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 $311 per night (USD)Expedia
From $155 per night (USD)VRBO
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $155 per night (USD)VRBO
From $959 per night (USD)Expedia
VILLA IN THE AIR - 2 Golf Carts, Private Pool, Steps to the beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Gorgeous 5 bedroom home with heated elevated pool. So much space at the poolside with sun-beds and screened outdoor liv ...
From $959 per night (USD)Expedia
From $808 per night (USD)VRBO
Ocean views, sleeps 10, heated pool, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
***Milton Update - We are happy to be accepting new bookings*** Featuring a private heated pool, a hot tub, ping pong, ...
From $808 per night (USD)VRBO
From $1226 per night (USD)VRBO
Special summer pricing! Luxury Beach House, Private Pool, just steps to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Do not miss the opportunity to enjoy a relaxing family friendly summer getaway at one of North Captiva's best properties ...
From $1226 per night (USD)VRBO
From $245 per night (USD)VRBO
The Quarterdeck Cottage~Boat dockage available directly across the street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With dockage (across the street at my privately owned property) and golf carts available for your stay (additional fee)B ...
From $245 per night (USD)VRBO
From $1272 per night (USD)VRBO
Peace of Paradise: Pvt., swing bar, pool, beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
(In recent news...The fall of 2024 was a challenging one for North Captiva Island due to hurricanes passing through. Pe ...
From $1272 per night (USD)VRBO
From $493 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 300 feet of seawall. This Villa is a fi ...
From $493 per night (USD)VRBO
From $705 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 $705 per night (USD)VRBO
From $488 per night (USD)VRBO
\"PERFECT SHELL\"LUXURY HOUSE STEPS 2 OCEAN*LRG POOL*FRONT BALCONY*AMENITY PACKED!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***Great Rates, Heated Pool Home, with an Excellent Island Location - High and Dry area which matters! And only Steps t ...
From $488 per night (USD)VRBO
From $402 per night (USD)Expedia
Matlacha Isles Oasis w\/ Gulf Access & Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
An unforgettable Matlacha Isles getaway awaits at this radiant 3-bedroom, 2.5-bathroom vacation rental. The vibrant home ...
From $402 per night (USD)Expedia
From $979 per night (USD)VRBO
Sanderella- Ocean Front Vacation Home w\/ Large Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Sanderella, North Captiva's most family-fun oriented rental with the best unobstructed views of the water and ...
From $979 per night (USD)VRBO
From $139 per night (USD)VRBO
Cozy, clean duplex with outdoor dinning.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Have your vacation in Paradise! This duplex is located in the heart of Pine Island a couple of blocks of the four way st ...
From $139 per night (USD)VRBO
From $259 per night (USD)VRBO
Yellow Fin Cabin of Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Famous Matlacha island with tourism and fishing. Many restaurants and bars at walking distance. The best fishing off a b ...
From $259 per night (USD)VRBO
Click For PricingExpedia
St James City Home on Canal w\/ Boat Davit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Whether you’re planning a snowbird retreat or a relaxing summer getaway, head to the canals of St James City for a stay ...
Click For PricingExpedia
From $817 per night (USD)VRBO
STUNNING BEACH HOME-Private Pool, Bar & Game Area. 2 Carts.\nALL YOU NEED IS FUN!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SAME OWNERS SAME HOME DIFFERENT NAME: A WAVE FROM IT ALL HAS CHANGED TO "ALL YOU NEED IS FUN" Are you ready for the be ...
From $817 per night (USD)VRBO
From $225 per night (USD)Expedia
Well Equipped Pet\/Smoke Free Family Home - bring your boat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WE DON'T LIVE IN A SQUARE WORLD, WHY VACATION IN A SQUARE HOUSE? Come and experience the unique feel of a round house de ...
From $225 per night (USD)Expedia
From $170 per night (USD)VRBO
Charming 2 Bedroom Vacation Home w\/ Pool and Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming getaway is nestled perfectly along Jug Creek with pool, tennis courts and boat slip. Large enough for the ...
From $170 per night (USD)VRBO
From $145 per night (USD)VRBO
Cozy Tropical Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy 2 bedroom /1 bath retreat - located on a quiet residential street. Within walking distance to boat ramp, kayak ren ...
From $145 per night (USD)VRBO
From $729 per night (USD)VRBO
Large home on private penninsula with water views on three sides
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Large four bedroom waterfront home built in 2008. Located on private peninsula at the end of private road with water on ...
From $729 per night (USD)VRBO
From $850 per night (USD)Expedia
Pirate's Captiva-Golf Cart and HOT Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise!! Golf cart included with your rental. Pirates Captiva was built in 2018, and withheld Hurricane lan ...
From $850 per night (USD)Expedia
From $91 per night (USD)VRBO
Saint James City- Southwest Fl little paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated 2 Bedroom, 2 bathroom with direct access. King bed in master bedroom with walk in closet. Twin beds in g ...
From $91 per night (USD)VRBO
From $473 per night (USD)Expedia
Reel Paradise! 2\/2 with So Much Waterfront! Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom two bath incredible home with water views from all angles! Large lot including, tiki wet-bar, plenty of spac ...
From $473 per night (USD)Expedia
From $761 per night (USD)VRBO
Endless Summer - In Search of the Perfect House in North Captiva, sleeps 10.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the Endless Summer for your next vacation getaway. Endless Summer is a 3 bedroom 2.5 bath home with a heated pool ...
From $761 per night (USD)VRBO
From $144 per night (USD)VRBO
Spacious apartment located within the heart of paradise.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A two-bedroom, two-bathroom, 2nd-floor apartment, located in a duplex on a dead-end road in the heart of Pine Island Cen ...
From $144 per night (USD)VRBO
From $438 per night (USD)VRBO
2B\/2B Private Heated Pool, Games, Golf Cart, Club Access, Updated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Thank you for your interest in Magic Po'Cean and North Captiva Island. Leave your car (and your cares) at Pineland Mari ...
From $438 per night (USD)VRBO
From $329 per night (USD)Expedia
Waterfront Haven w\/ Floating Dock, Alfresco Living, Two Suites & Yard
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 2
Matlacha Mermaid Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $329 per night (USD)Expedia
From $219 per night (USD)VRBO
Dog-Friendly, Canal-Front Home with Canal Access, Central AC, and WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Flamingo Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $219 per night (USD)VRBO
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Beautiful Monthly Condo at the Buccaneer. Minutes from off shore fishing.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The one bedroom one bathroom condo available minutes from Matlacha Florida. The Buccaneer is located on Pine Island and ...
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From $183 per night (USD)VRBO
The Crab Shack - Fully-equipped and Updated 2-bedroom Waterfront Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
* We survived IAN, we have completely remodeled and are back to being fully functional. ** Get away to the Crab Shack, ...
From $183 per night (USD)VRBO
From $780 per night (USD)VRBO
Windows on the Water \"W.O.W\" An ocean front oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
House, 3 bedrooms - 3 full bath. Our renovated home is named "Windows on the Water" because of the spectacular wall of ...
From $780 per night (USD)VRBO
From $246 per night (USD)VRBO
Waterfront condo located in the waterfront paradise of Bokeelia
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Incredible waterfront views in this fully stocked Bocilla Island Club condominium. This is an end unit which gives a pan ...
From $246 per night (USD)VRBO
From $238 per night (USD)Expedia
Pine Island Private Getaway with Dock! (CDC Safe)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Absolutely the best location and value on Pine Island! Beautifully designed, spacious and private two bedroom home with ...
From $238 per night (USD)Expedia
From $506 per night (USD)VRBO
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This charming home is in the perfect location on North Captiva Island. The private heated pool and hot tub won’t stop yo ...
From $506 per night (USD)VRBO
From $393 per night (USD)VRBO
North Captiva Island Beach House\/60 Second Walk to 4 Miles of Awesome Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
***** GOLF CART AVAILABLE WITH RENTAL***** Winterhaven 4550 Oyster Shell Drive North Captiva Island, Florida NORTH CAPTI ...
From $393 per night (USD)VRBO
From $362 per night (USD)VRBO
Bokellia Tarpon Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island life Begins here. Waterfront canal. Take Your boat to Cabbage Key Boca grande Caya costa. Tarpon Capital of the W ...
From $362 per night (USD)VRBO
From $761 per night (USD)VRBO
Kaya Del Sol, the perfect family trip!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a magical island paradise! This quintessential family or couples' retreat inspires a relaxed peaceful ambience ...
From $761 per night (USD)VRBO
From $360 per night (USD)VRBO
Come spend some island time at Reel Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Reel Paradise is a two bedroom two bathroom house on a fenced in large lot located in Matlacha, Florida. The inside is f ...
From $360 per night (USD)VRBO
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Sophisticated home with private pool & fast WiFi - walk & ferry to attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Eagles Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For PricingExpedia