Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $474 per night (USD)VRBO
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Incredible newly renovated 3 bedroom home with gulf views! Open layout with exceptional outdoor spaces including huge fr ...
From $474 per night (USD)VRBO
From $406 per night (USD)VRBO
Florida Island Paradise Home, Bokeelia Canal, Pine Island, w\/Pool & Boat Lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Time Inn! This 3 BR, 3 bath private home is located in Bokeelia Isles, Pine Island, Florida. Welcome ...
From $406 per night (USD)VRBO
From $193 per night (USD)VRBO
Gulf Hidden Jewel POOL Kayak bikes fish from dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Time! Gulf access waterfront oasis. New pool! Two bedrooms, 1 full bath, full size kitchen and washer/ ...
From $193 per night (USD)VRBO
From $369 per night (USD)Expedia
Tropical Oasis Pool Kayak Bikes fish from dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Island Time! Gulf access waterfront home. New Pool Great for family or groups sharing. 3 bedrooms, 2 full ba ...
From $369 per night (USD)Expedia
From $133 per night (USD)VRBO
Sunrise In Paradise POOL Kayak bikes fish from dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Island Time! Gulf access waterfront oasis. New pool ! 1 bedroom, 1 full bath with bath tub, 1 kitchen, washer ...
From $133 per night (USD)VRBO
From $1665 per night (USD)VRBO
Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Stunning sunset views and superior craftsmanship combine with casual elegance in this reverse floor plan beach home, des ...
From $1665 per night (USD)VRBO
From $760 per night (USD)VRBO
LVCC Villa Green Adventure
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This spectacular Vacation Villa will take you on a green adventure, in more than one way. Firstly, when thinking of the ...
From $760 per night (USD)VRBO
From $339 per night (USD)VRBO
Island Getaway Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3Bedroom 2 bath remodeled pool home in St James City Triple lot with plenty of privacy with huge 13' deep pool with a wa ...
From $339 per night (USD)VRBO
From $381 per night (USD)VRBO
House on Matlacha Pass with pool, hot tub, kayak dock & 12k lb boat lift!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our spacious open concept home with a great outdoor living space that opens up fully to a lanai overlooking the Ma ...
From $381 per night (USD)VRBO
From $567 per night (USD)Expedia
Waterfront Property with Dock and 2 Minute Walk to the Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful, brand new, resort style, four bedroom home just completed in October, 2020 and located right on Rum Road; wal ...
From $567 per night (USD)Expedia
From $920 per night (USD)VRBO
Beachy Keen, newly constructed pool home near beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
A stay in Paradise! Beautifully appointed, newly built home on your own secluded Upper Captiva island. 3 bedroom 2.5 b ...
From $920 per night (USD)VRBO
From $353 per night (USD)VRBO
A Personal Waterfront Micro-Resort on SW Florida's Pine Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
The Coconut Cabana is BACK after much clean up and repair from the past Hurricanes Ian, Helene and Milton. This is a ver ...
From $353 per night (USD)VRBO
From $1509 per night (USD)VRBO
BEACHFRONT, HEATED POOL, KAYAKS\/SUP, LANAI W\/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
* ALWAYS CLEANED AND SANITIZED BY A PROFESSIONAL CLEANING SERVICE!! Welcome to North Captiva Island, a private, bridge-l ...
From $1509 per night (USD)VRBO
From $154 per night (USD)Expedia
Comfortable and relaxing house located on a deep water canal.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute little house located on a deep water canal in the heart of Matlacha. Hurricane Milton was a true disaster for most ...
From $154 per night (USD)Expedia
From $286 per night (USD)VRBO
Peacock Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Awesome Matlacha Beauty- Vacation Rental, perfect for snowbirds & your little furry friend too!! Enjoy the warm Florida ...
From $286 per night (USD)VRBO
From $291 per night (USD)Expedia
☀️TRANQUILITY VILLA☀️
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the ...
From $291 per night (USD)Expedia
From $303 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 $303 per night (USD)VRBO
From $582 per night (USD)Expedia
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 $582 per night (USD)Expedia
From $486 per night (USD)VRBO
2B\/2B Private Heated Pool, Golf Cart, Club Access, Games,
- 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 $486 per night (USD)VRBO
From $132 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 $132 per night (USD)VRBO
From $628 per night (USD)VRBO
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $628 per night (USD)VRBO
From $402 per night (USD)Expedia
North Captiva Island Beach House\/60 Second Walk to 4 Miles of Awesome Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
***** NEW GOLF CART WITH RENTAL***** Winterhaven 4550 Oyster Shell Drive North Captiva Island, Florida NORTH CAP ...
From $402 per night (USD)Expedia
From $1086 per night (USD)VRBO
Peace of Paradise: Pvt. Waterfall Pool, Swing Bar!
- 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 $1086 per night (USD)VRBO
From $1041 per night (USD)Expedia
Exclusive Summer Specials! Luxury Beach House, Private Pool, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Your Perfect Summer Escape Awaits at La Casa Del Sol! Exclusive Summer Specials – Book Your Stay Today! After an exten ...
From $1041 per night (USD)Expedia
From $924 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 $924 per night (USD)VRBO
From $456 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 $456 per night (USD)VRBO
From $134 per night (USD)VRBO
Reopened in November 2024
- 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 $134 per night (USD)VRBO
From $396 per night (USD)Expedia
North Captiva Point House - Boat\/Water Taxi Only **NEWLY RENOVATED **
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
****This property can only be accessed by boat or water taxi.**** The North Captiva Point House was built by Barnacle ...
From $396 per night (USD)Expedia
From $129 per night (USD)VRBO
Serenity Bay #2 Street-side
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This is a studio apartment, with a queen bed, kitchen with two burner cook top, microwave, toaster, coffee pot, and 4 cu ...
From $129 per night (USD)VRBO
From $388 per night (USD)VRBO
LUXURY ISLAND RENTAL\/CLUB w\/POOL, KAYAKS, 4BR PRIV BEACH ACCESS, BOAT DOCK AVAIL
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
FANTASTIC NEW LUXURY ISLAND RENTAL! OPEN and WELCOMING GUESTS! ONE 4 PERSON GOLF CART INCLUDED COMPLIMENTARY IN YOUR VAC ...
From $388 per night (USD)VRBO
From $270 per night (USD)VRBO
Prettiest Sunset View Pine Island, Waterfront Home on Water
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome This is the fishermans delight. In addition to staying in the hous ...
From $270 per night (USD)VRBO
From $271 per night (USD)VRBO
Skipper Lane on Salt Water Canal, Easy Gulf access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated, Open Concept 2 Bed 2 Bath Gulf Access Home in the Heart of St. James City. Fisherman’s Dream Awaits!! Two Man ...
From $271 per night (USD)VRBO
From $281 per night (USD)VRBO
My Only Sunshine Island Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our beautifully remodeled 2-bedroom, 2-bath POOL HOME nestled on a canal leading to Matlacha Pass in the pict ...
From $281 per night (USD)VRBO
From $130 per night (USD)Expedia
*** Studio Tarpon located directly on the Gulf of Mexico ***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Tarpon Suite" in a house with 4 apartments by the water - Cute studio for max. 3 persons - living area with slee ...
From $130 per night (USD)Expedia
From $293 per night (USD)VRBO
Remodeled 3\/2 on quiet canal with 10k boatlift, 5 mins to Charlotte Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Up and running after hurricane Ian and accepting seasonal rentals! the property has a new metal roof and seawall and wor ...
From $293 per night (USD)VRBO
From $259 per night (USD)VRBO
Paradise just waiting for you!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you are looking for an awesome get-a-way, we have the place for you! If you love to fish, swim or just enjoy the Flo ...
From $259 per night (USD)VRBO
From $572 per night (USD)VRBO
Great Island Retreat- Walk to Beach and Pools
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
PLEASE CONTACT US ABOUT DISCOUNTS FOR RENTALS GREATER THAN 14 DAYS. ALSO FOR STAYS OF 4 DAYS MAXIMUM GUEST COUNT IS 6 ...
From $572 per night (USD)VRBO
From $397 per night (USD)Expedia
SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
‼️ASK ABOUT LAST-MINUTE BOOKING SPECIALS‼️ TRUE ISLAND EXPERIENCE: Steps from the water and right next to the bay, The ...
From $397 per night (USD)Expedia
From $1258 per night (USD)VRBO
Serendipity is BACK - Complete remodel April 2024 - Pool; 2 Golf Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Serendipity beach house is Back and is Better than ever with a COMPLETE REMODEL finished April 2024. Located one hu ...
From $1258 per night (USD)VRBO
From $179 per night (USD)VRBO
Cottage with private deck in the heart of Matlacha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a small cottage with an attached in-law unit, that has the option to rent the house as a 2-bed bath due to this ...
From $179 per night (USD)VRBO
From $213 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Reel Suite". Compared t ...
From $213 per night (USD)VRBO
From $974 per night (USD)VRBO
Bluefin Beach House, Luxury Home with Pool & Spa on North Captiva, 2 Golf Carts
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Bluefin Beach House is a professionally designed and decorated beach home located just 300 feet from the Gulf of Mexico ...
From $974 per night (USD)VRBO
From $247 per night (USD)VRBO
Fisherman's Paradise on the Canal with Covered Boat Lift and Dock\/ Gulf Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please come and enjoy our beautiful 3 BR/2BA 1865 Sq ft home located in the quaint fishing village of Matlacha. Matlach ...
From $247 per night (USD)VRBO
From $91 per night (USD)VRBO
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore Pine Island and the Florida Gulf Coast from this retro two-room cottage set in a pretty back yard. 45 min from F ...
From $91 per night (USD)VRBO
From $198 per night (USD)VRBO
Pine Island Retreat 2\/2 on Canal!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Pine Island treasure is conveniently located in Flamingo Bay. 2 bedroom 2 bathroom. Each room has it's own full bat ...
From $198 per night (USD)VRBO
From $214 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Lure Suite". Compared t ...
From $214 per night (USD)VRBO
From $312 per night (USD)VRBO
ISLAND LIVING, BOATER'S PARADISE, AND MODERN LUXERY !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
If you want it all in a vacation home, this Gulf access waterfront home is the gem you have been looking for. Do you ne ...
From $312 per night (USD)VRBO
From $262 per night (USD)Expedia
Kinsey's Beach Shack- Perfect getaway for two!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The North Captiva Fish Camp is located on the peninsula of the island nestled between Safety Harbor and Pine Island Soun ...
From $262 per night (USD)Expedia
From $1253 per night (USD)VRBO
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 18
Overview of the property: • No Worries Atoll is a stunning 3,300 square foot pool home that is currently being complete ...
From $1253 per night (USD)VRBO
From $143 per night (USD)VRBO
Waterfront Home - Cherry Properties Pine Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a beautiful fully furnished 2004 Manufactured Home. The home was remodeled and updated in Fall of 2021. In addit ...
From $143 per night (USD)VRBO
From $671 per night (USD)VRBO
World Class Fishing, direct canal on Gulf of Mexico, 3\/3, boat lift, heated pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Luxury waterfront home with heated pool, direct Gulf access with private docking for your boat. Open concept layout with ...
From $671 per night (USD)VRBO
From $904 per night (USD)Expedia
Escape To Paradise - Breathtaking Views- Pool-Steps to the beach - 2 Golf Carts!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Escape To Paradise Beach House , a spectacular 4 bedroom, 4 bathroom home that sleeps 10- Completely remo ...
From $904 per night (USD)Expedia
From $176 per night (USD)VRBO
Fishermen, Kayakers & Birdwatchers Paradise -Fish in 5 Minutes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 3
Location: Bokeelia, Pine Island, Florida South West Florida, USA (25 miles to Fort Myers International Airport) A fishe ...
From $176 per night (USD)VRBO
From $115 per night (USD)VRBO
St. James City; Pine Island Cove- 55 yrs and older Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Private home located on the canal-2 bedrooms/2 bathrooms in a 55 yr and older community. Only 2 guests full time and on ...
From $115 per night (USD)VRBO
From $263 per night (USD)VRBO
Hurricane Ian update Roofs are on pools are heated life rolls on Thank God
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Beautifully upgraded yet very comfortable condo it the best fishing spot! Over looking the pool and watet inlet. Enjoy t ...
From $263 per night (USD)VRBO
From $162 per night (USD)VRBO
Serenity Bay Studio 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
On the same property as Serenity Bay Cottages, Big House, is a 4 plex, with four studio apartments. Each about 250 sq. ...
From $162 per night (USD)VRBO
From $1272 per night (USD)VRBO
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Since 2017, "The Blue Marlin" has provided sea-loving families with the ultimate North Captiva beachfront retreat. This ...
From $1272 per night (USD)VRBO
From $1067 per night (USD)Expedia
Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Newly remodeled (2025) Luxury 4 BR/5 BA - Brand New Kitchen and Baths – Close to beach, Island Club and Preserve, yet a ...
From $1067 per night (USD)Expedia
From $361 per night (USD)VRBO
Laid Back Old Florida Style Home with Pool and Hammock Gardens
- 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 ...
From $361 per night (USD)VRBO
From $261 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 $261 per night (USD)VRBO
From $311 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 $311 per night (USD)VRBO
From $374 per night (USD)VRBO
Calling Waters-Gulf access w\/dock, pool and HT.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning canal front home in Southwest Florida features a heated pool, a private dock that can accommodate a 25-foo ...
From $374 per night (USD)VRBO
From $166 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 $166 per night (USD)VRBO
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 $233 per night (USD)Expedia
Soak up Paradise and Relax in Heated Pool\/Spa Home surrounded by Happy Wildlife
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Heated Salt Water Pool and Spa on Marble Lanai, with large screened enclosure. This side-by-side home is fully equipped ...
From $233 per night (USD)Expedia
From $207 per night (USD)VRBO
Beautiful \"Old Florida\" Pine Island Golf Course & Marina Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $207 per night (USD)VRBO
From $570 per night (USD)Expedia
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $570 per night (USD)Expedia
Click For PricingVRBO
Canal Front Home , direct Gulf access with lanai and dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and enjoy your 2/2 home. Perfect secluded waterfront location.with your private dock, You are minutes away Sanibe ...
Click For PricingVRBO
From $863 per night (USD)VRBO
All Conched Out - Luxe 3 Br, Private pool, outdoor pool table - pets considered
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
All Conched Out This adorable “pink palace” retreat has everything you need for a fun, wonderful and relaxing vacation ...
From $863 per night (USD)VRBO
From $316 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 $316 per night (USD)VRBO
From $447 per night (USD)Expedia
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)Expedia
From $464 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 $464 per night (USD)VRBO
Click For PricingExpedia
Moonshine Acres Tropical Horse Farm
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Moonshine Acres is located in the historic Saint James section of Pine Island. Our home is conveniently located near num ...
Click For PricingExpedia
From $247 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 $247 per night (USD)VRBO
From $134 per night (USD)VRBO
Reopened in November 2024
- 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 $134 per night (USD)VRBO
From $144 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 $144 per night (USD)VRBO
From $660 per night (USD)Expedia
LAST MINUTE SPECIAL RATE! MARCH 9-16 400\/night! 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 $660 per night (USD)Expedia
From $385 per night (USD)VRBO
WARM! Spectacular Nature! Waterfront! Prime Fishing! Bring Boat, 2 Free Kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tired of the cold? This place is HOT! Taking reservations for 2025. No hurricane damage. Fishing enthusiasts, kayakers, ...
From $385 per night (USD)VRBO
From $1056 per night (USD)Expedia
BE AT THE BEACH: Private Pool, Golf Cart, Club Access included, 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 $1056 per night (USD)Expedia
From $403 per night (USD)VRBO
Rockstar Beach House North Captiva Island, 25’ boat slip, NCIC pools, golf cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*NORTH CAPTIVA AND THIS HOUSE ARE ONLY ACCESSIBLE BY FERRY BOAT. ...
From $403 per night (USD)VRBO
![☀︎🏝⛱︎ Beachfront Elegance⛱︎🏝☀︎ \n[2025 Spring + Summer Weeks Available Now!]](https://d1g8n4w8yie14k.cloudfront.net/lodging/19000000/18770000/18767200/18767197/6055b3c8.jpg?impolicy=ccrop&w=350&h=233&q=medium)
From $917 per night (USD)Expedia
☀︎🏝⛱︎ Beachfront Elegance⛱︎🏝☀︎ \n[2025 Spring + Summer Weeks Available Now!]
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our unique, fully renovated island home is 75 steps from the beach with spectacular panoramic views. Spring -> Summer ...
From $917 per night (USD)Expedia
From $618 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 $618 per night (USD)VRBO
From $511 per night (USD)Expedia
Newly Renovated Island Pool Home\nLast minute get 2 nights free March 8th
- 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 $511 per night (USD)Expedia
From $904 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 $904 per night (USD)VRBO
From $840 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 $840 per night (USD)Expedia
From $1072 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 $1072 per night (USD)VRBO
From $764 per night (USD)VRBO
Wicked Dolphins: Private Pool, Tiki Bar & Golf Cart Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Wicked Dolphins, your perfect island getaway on North Captiva Island. This 3-bedroom, 2-bathroom beach view h ...
From $764 per night (USD)VRBO
From $617 per night (USD)VRBO
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 $617 per night (USD)VRBO
From $610 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 $610 per night (USD)VRBO
From $401 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 $401 per night (USD)VRBO
From $199 per night (USD)Expedia
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 $199 per night (USD)Expedia
From $293 per night (USD)VRBO
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 $293 per night (USD)VRBO
From $260 per night (USD)Expedia
Bokeelia Bliss! 3\/3 Heated Pool, Boat Ramp Included!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Captain's Cove Treasure Discover the perfect getaway in this 3-bedroom, 3-bathroom home with a heated pool and a stunni ...
From $260 per night (USD)Expedia
From $2868 per night (USD)VRBO
Beachfront! 2 Houses - Sleeps up to 16!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: 🌊 Gulf Front! 🏠2 professionally decorated homes 🛋️Sleeps 16 comfortably 🛥️ Shared boat dock - ask about ava ...
From $2868 per night (USD)VRBO
From $454 per night (USD)Expedia
House in Florida - Gulf of Mexico - Pine Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 6
<p>Located in Bokeelia, this 4-bedroom, 5-bathroom vacation home lets you experience it all. Fans of nature and the outd ...
From $454 per night (USD)Expedia
From $147 per night (USD)VRBO
1\/1 Condo in St. James City! Boat Slip Included!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming 1/1 Condo in St. James City! This cozy one-bedroom, one-bath condo offers beautiful views of the Monroe Canal. ...
From $147 per night (USD)VRBO
From $525 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 $525 per night (USD)VRBO
From $187 per night (USD)VRBO
Charming Cottage in St. James City – Seasonal Rental with Boat Lift!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Charming Cottage in St. James City – Seasonal Rental with Boat Lift! Escape to this cozy retreat, perfect for one couple ...
From $187 per night (USD)VRBO
From $464 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 $464 per night (USD)VRBO