Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $855 per night (USD)
VRBO
SPRAWLING PRIVATE BEACHFRONT - Sleeps 10, perfect for a family, 2 golf carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to SEA LA VIE beach house, your luxurious home away from home at the shore. Our private 4 bedroom beach house of ...
From $855 per night (USD)VRBO
- From $864 per night (USD)
Expedia
\"FLORIDAYS\" Newly Completed Private Beach House w\/ Heated Pool & Spa. 2 Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Photos updated December 2023 “FLORIDAYS" Completed in 2019, this new custom-designed and crafted 4 bedroom, 4 full bath ...
From $864 per night (USD)Expedia
- From $204 per night (USD)
VRBO
3 bed, 3 bath home, heated\/cooled pool on quiet canal. Quick boat access to gulf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Treehouse is a well appointed comfortable three bedroom three bathroom home, with a heated pool, situated on a tranquil ...
From $204 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nice relaxing townhome…. Simple, white, clean…. A few steps from the harbors edge. Great place to escape from work, or ...
From $290 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Waterfront Gulf Access- Just a few minutes to Big Water.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
The San Carlos Bay is across the street. If it's fishing and boating you want then this home could be perfect for you. B ...
From $179 per night (USD)VRBO
- From $333 per night (USD)
Expedia
Bokeelia Island Oasis: Waterfront, Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Get a taste of island living at this delightful 3-bedroom, 3-bath Bokeelia escape! Ideally located at the tip of Pine Is ...
From $333 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
Completely remodeled & prof design after hurricane! Open Jun 1! Lrg 5Bdr! Pool!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
*This property is located on North Captiva which is only accessible by ferry or boat. * North Captiva Island is a remot ...
From $1000 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Fisherman's Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Here is an opportunity to rent one of the best waterfront units on Pine Island. The gorgeous views are across the water ...
From $150 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Island Hideaway in Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunny 2 bedroom/bathroom house located right on canal in beautiful Matlacha Island. This house features a screened in fr ...
From $175 per night (USD)VRBO
- From $99 per night (USD)
VRBO
Quiet and Cozy Island Retreat. Beautifully Remodeled.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Enjoy your privacy and peace at our recently renovated Bokeelia Get-Away. This Vacation home is designed for two with r ...
From $99 per night (USD)VRBO
- From $925 per night (USD)
VRBO
ON THE WATER! Best sunsets, best beach, toes in the sand BeachBar, 5 Star rated!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Water front Beach House, ON THE BEACH! Newly added "Flip Flops Beach Bar" on the sand! Full wrap around decks, best view ...
From $925 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Studio Condo, just minutes from Charlotte Harbor and great island shopping!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Captains Cove waterfront end unit-Studio condo, 1 Bath, second floor, with parking under unit. Queen size Murphy bed an ...
From $100 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Beautiful \"Old Florida\" Pine Island Golf Course & Marina Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a lovely, updated 4/3 stilt home located directly on the Alden Pines Golf Course and only 1/2 block from the Pin ...
From $175 per night (USD)VRBO
- From $517 per night (USD)
VRBO
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
***Post Hurricane Ian Update 6/1/23*** Thank you for your interest in Tarpon Cove. We’re happy to report that the isla ...
From $517 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Beautiful water-view home close to boat ramp, fishing and Gulf of Mexico.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to "Sealaxation House". Beautiful canal-side, two-story home. You'll feel like you're in a treehouse. Property ...
From $215 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Soak up Paradise as you Relax in Pool\/Spa Home surrounded by Happy Wildlife
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
New in 2021 Heated Salt Water Pool and Spa on Marble Lanai, with screened enclosure. This side-by-side home is 7 years y ...
From $185 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Private St James City Home w\/ Enclosed Deck!
- 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 $217 per night (USD)VRBO
- From $600 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 $600 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Island Oasis- Olde Florida Keys atmosphere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Forget your worries in this spacious and serene space. Come & relax on this Olde Florida Vibe Island, there is so much ...
From $130 per night (USD)VRBO
- From $467 per night (USD)
VRBO
GORGEOUS BEACH HOUSE 4 BRS, PRIVATE POOL, 360 H2O Views 2 Carts, Outdoor Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
FANTASTIC OPPORTUNITY! BEAUTIFUL HOME! GREAT RATES! BOOK NOW! Thank you for your interest in Paloma Beach House! Book u ...
From $467 per night (USD)VRBO
- From $75 per night (USD)
VRBO
Spacious Getaway, 1 to 4 for Easy Going Nature Lovers on beautiful Pine Island.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Comfy home w pretty garden on historic Pine Island. Nearby fishing, kayaking, birding, good eats, tennis. Visit pristine ...
From $75 per night (USD)VRBO
- From $808 per night (USD)
VRBO
May last min. SPECIAL! 650 a night! Heated pool, private beach access, Boat Bar!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Recently updated, 5 Star Property! We are located on the northern tip of North Captiva Island, with lots of privacy away ...
From $808 per night (USD)VRBO
- From $1192 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 $1192 per night (USD)VRBO
- From $882 per night (USD)
Expedia
BLUE MANGO -- Tropical Seclusion Steps from the Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
**** Under New Property Management as of 04/2022 **** **THE FUN STUFF** Only 100 feet from 4 MILES OF WHITE SAND BEACH ...
From $882 per night (USD)Expedia
- From $118 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 $118 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $160 per night (USD)
VRBO
\"The Mermaid\" - Living in a Lush Tropical Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Vacation Rental: Newly renovated cottage on Pine Island near Fort Myers, Florida. #YesVrbo Perfect couple's getaway. ...
From $160 per night (USD)VRBO
- From $1531 per night (USD)
Expedia
Beachfront🌊4 KING suites&bunk room🛏️Pet Friendly🐾
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
🛥️New offering: Free boat dock 👙GULF FRONT 180° amazing beach views 🏠Professionally designed/decorated 🛌🏽Westin Hea ...
From $1531 per night (USD)Expedia
- From $379 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 $379 per night (USD)VRBO
- From $150 per night (USD)
Expedia
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 $150 per night (USD)Expedia
- From $1100 per night (USD)
VRBO
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 $1100 per night (USD)VRBO
- From $88 per night (USD)
VRBO
Reopened in November 2023!!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $88 per night (USD)VRBO
- From $415 per night (USD)
VRBO
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 $415 per night (USD)VRBO
- From $600 per night (USD)
Expedia
The Salty Conch - Luxury Just Steps To The Beach with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- 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 $600 per night (USD)Expedia
- From $218 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 $218 per night (USD)VRBO
- From $126 per night (USD)
Expedia
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 $126 per night (USD)Expedia
- Click For Pricing
VRBO
Relaxing Island View!
- 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 ...
Click For PricingVRBO
- From $239 per night (USD)
VRBO
LUXE TOWNHME CLUB w\/POOL! 4 BRs, 2 KINGS, KAYAKS & GOLF CART INC, 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 $239 per night (USD)VRBO
- From $793 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 APRIL BOOKINGS (Inqu ...
From $793 per night (USD)VRBO
- From $205 per night (USD)
Expedia
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 $205 per night (USD)Expedia
- From $286 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 $286 per night (USD)VRBO
- From $104 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $104 per night (USD)VRBO
- From $119 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 $119 per night (USD)VRBO
- From $237 per night (USD)
Expedia
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 $237 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $105 per night (USD)VRBO
- From $130 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 $130 per night (USD)VRBO
- From $162 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 $162 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Newly Renovated Beach House! Book your Spring Break and \nSummer Vacations Now!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Relax and enjoy this unique piece of island paradise from our Spacious, custom designed, professionally decorated, luxur ...
From $650 per night (USD)Expedia
- From $295 per night (USD)
VRBO
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 $295 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Fun'n Sun - Charming 3 BR\/ 3 baths waterfront Villa w. boat lift
- 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 $250 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful & laid back pool house!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome!! Fish & Sips is a gorgeous, "Old Florida" style home located on Pine Island. It is a hidden gem for fishing and ...
Click For PricingVRBO
- From $219 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 $219 per night (USD)VRBO
- From $744 per night (USD)
VRBO
This Island Treasure has it all! Pool-Golf Cart -Dock-Airstrip-Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Fish in your back yard off the dock, Play in your private heated pool, Entertain on your cabana / pool deck, Watch sun r ...
From $744 per night (USD)VRBO
- From $600 per night (USD)
Expedia
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 $600 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Captiva Beach Sunset ~Gulf front, pool, NCIC, 4 & 6 seater carts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Captiva Beach Sunset - 5 BR/4.5 BA - Sleeps 12 in beds- Beachfront with Private Pool Queen size air mattress is availabl ...
From $1400 per night (USD)VRBO
- From $119 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 $119 per night (USD)VRBO
- From $154 per night (USD)
VRBO
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 $154 per night (USD)VRBO
- Click For Pricing
VRBO
Private Pool Home Spectacular Sunsets Steps from the Beaches & StarLink Internet
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Your search for the PERFECT beach vacation house is over with your search for "Captiva Isles on North Captiva Island, FL ...
Click For PricingVRBO
- From $536 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 $536 per night (USD)VRBO
- From $105 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 $105 per night (USD)VRBO
- From $110 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 $110 per night (USD)VRBO
- From $558 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 $558 per night (USD)VRBO
- Click For Pricing
VRBO
Pool Home, Steps from the Beach and Spectacular Sunsets plus StarLink Internet
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Your search for the PERFECT beach vacation house is over with your search for "Havana Breeze on North Captiva Island, FL ...
Click For PricingVRBO
- From $135 per night (USD)
VRBO
Pine Island Condo in beautiful Bokeelia, Florida 2 bed, 2 1\/2 bath, w\/boat dock
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Stay at Bocilla Island Club and enjoy this beautiful 2 bedroom, 2 1/2 bath condo featuring a king size bed and a queen ...
From $135 per night (USD)VRBO
- From $152 per night (USD)
VRBO
Saint James hidden gem. 3\/2 canal front home with 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 $152 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Spacious home hot tub, bring boat pacman dock Xtra parking. Walk 2 restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Gulf Access- Embrace the perfect fishing vacation spot for small or larger groups that won't break the bank. Weekley & m ...
From $237 per night (USD)Expedia
- Click For Pricing
VRBO
Moonshine Acres Tropical Horse Farm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Moonshine Acres is located in the historic Saint James section of Pine Island. Our home is conveniently located near num ...
Click For PricingVRBO
- From $184 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 $184 per night (USD)Expedia
- From $199 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 $199 per night (USD)VRBO
- From $363 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 $363 per night (USD)VRBO
- From $390 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 $390 per night (USD)VRBO
- From $419 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 $419 per night (USD)VRBO
- From $200 per night (USD)
VRBO
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 $200 per night (USD)VRBO
- From $843 per night (USD)
VRBO
Steps from the beach, gulf views, on the airstrip and Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
If you are searching for an island vacation that is different from all others, then search no more for you have stumbled ...
From $843 per night (USD)VRBO
- From $536 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 $536 per night (USD)VRBO
- From $430 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 $430 per night (USD)VRBO
- From $650 per night (USD)
VRBO
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 $650 per night (USD)VRBO
- From $699 per night (USD)
VRBO
May, Last min SPECIAL 599 ON THE WATER! Best beach & Sunsets on island! 5 Stars!
- 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 $699 per night (USD)VRBO
- From $420 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 $420 per night (USD)VRBO
- From $600 per night (USD)
Expedia
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 $600 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Spectacular Nature! Waterfront! Prime Tarpon Fishing! Bring Boat, Free Kayak! 🎣
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tired of the cold? Need a warm & tropical place to stay? Let’s Go! Fishing enthusiasts, kayakers, bird watchers, nature ...
From $313 per night (USD)VRBO
- From $1009 per night (USD)
Expedia
Exclusive At the Beach: Pvt Pool, Golf Cart, Club Access, FL Sunshine! Book Now!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Gulf Swells & Sea Shells – your ultimate oceanfront haven! Completely renovated in 2020/21, this stunning 5-b ...
From $1009 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Rockstar Beach House North Captiva Island …accessible by ferry boat only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
** UPDATE ** Rockstar has many recent upgrades including a new Reverse osmosis system in the kitchen, added Super fast S ...
From $366 per night (USD)VRBO
- From $89 per night (USD)
Expedia
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $89 per night (USD)Expedia
- From $372 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 $372 per night (USD)VRBO
- Click For Pricing
Expedia
Ocean Boulevard-New Steps To The Beach - Professionally Decorated -2 Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Breathtaking elegance awaits you at the Ocean Boulevard located approximately 400 feet from the gulf. This brand new (s ...
Click For PricingExpedia
- From $91 per night (USD)
VRBO
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $91 per night (USD)VRBO
- From $815 per night (USD)
VRBO
TIPSY TURTLE - awesome pool, 4 decks, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
We’d like to welcome you to…Tipsy Turtle! TIPSY TURTLE - Located on North Captiva Island; this property is accessed by f ...
From $815 per night (USD)VRBO
- From $343 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 $343 per night (USD)VRBO
- From $103 per night (USD)
Expedia
Reopened in November 2023 !!!
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $103 per night (USD)Expedia
- From $150 per night (USD)
VRBO
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 $150 per night (USD)VRBO
- From $105 per night (USD)
Expedia
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 $105 per night (USD)Expedia
- From $693 per night (USD)
VRBO
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 $693 per night (USD)VRBO
- From $735 per night (USD)
Expedia
Ocean views, sleeps 10, heated pool, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
4/20 to 4/27 is available and priced to book!! Featuring a private heated pool, a hot tub, ping pong, foosball, cornho ...
From $735 per night (USD)Expedia
- From $1080 per night (USD)
VRBO
Luxury Beach House, Completely Remodeled. Special pricing for Summer!!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
HIGH SPEED INTERNET - We now have Starlink satellite high speed internet, providing speed of up to 400 MBS, so work from ...
From $1080 per night (USD)VRBO
- From $238 per night (USD)
Expedia
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 $238 per night (USD)Expedia
- From $885 per night (USD)
VRBO
Peace of Paradise - Private Pool & 2 Golf Carts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
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 $885 per night (USD)VRBO
- From $179 per night (USD)
Expedia
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 $179 per night (USD)Expedia
- From $550 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 $550 per night (USD)VRBO
- From $340 per night (USD)
VRBO
\"PERFECT SHELL\"LUXURY HOUSE STEPS 2 OCEAN*LRG POOL*FRONT BALCONY*AMENITY PACKED!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***Current Openings for 2024 are 4 /20-4/29, 5/17-5/25 6/15 - 6/22, 7/20-7/27 on! Great Rates, Private Pool Home, with ...
From $340 per night (USD)VRBO