Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $223 per night (USD)VRBO
Seaside Villa Destin - Single home with privat pool in the heart of Pine island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our Seaside Villa Destin is idyllically located on Pine Island, which is situated in front of Cape Coral. Especially for ...
From $223 per night (USD)VRBO
From $259 per night (USD)VRBO
Unique Charlotte Harbor experience on a comfortable Schucker 436 trawler.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boaters Only at this time. I want to welcome boaters to an experience of a lifetime! You must have a boat that you can ...
From $259 per night (USD)VRBO
From $386 per night (USD)VRBO
The Bokeelia Boathouse, waterfront, Boat Dock, Pine Island, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise awaits you at our recently renovated island get away home. Located on the water in Bokeelia on Pine Island we ...
From $386 per night (USD)VRBO
From $762 per night (USD)Expedia
Beach's Edge, On the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful home is right on the Florida sugar sand beach, which is often uninhabited except by wading birds, ghost c ...
From $762 per night (USD)Expedia
From $725 per night (USD)VRBO
Perfect Placement, A beautiful beachfront home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home (sleeps 6 adults and 4 children) is extremely close to the ocean and a Florida sugar sand beach whic ...
From $725 per night (USD)VRBO
From $1072 per night (USD)Expedia
New luxury pool home, 2 min to beach, 360 water views, club available
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 19
Overview of the property: • Sublime is a new, stunning 3,200 square foot, 7-bedroom, 6-bathroom, luxury beach home w/ s ...
From $1072 per night (USD)Expedia
From $336 per night (USD)VRBO
Canal Life On Matlacha!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Canal life says it all as you relax in this unique spacious home on the quaint little island of Matlacha. Sleeps 8 easil ...
From $336 per night (USD)VRBO
From $719 per night (USD)Expedia
BEAUTIFUL OCEANFRONT BEACH LOCATION - View dolphins & Manatees from Living Room!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
This oceanfront 6 bedroom home is located on North Captiva Island and can accommodate up to 16 people. It comes with th ...
From $719 per night (USD)Expedia
From $506 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 $506 per night (USD)VRBO
From $317 per night (USD)Expedia
Florida Island Paradise Home, Bokeelia Canal, Pine Island, w/Pool & Boat Lift
- Bedrooms:
- 1
- 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 $317 per night (USD)Expedia
From $184 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 $184 per night (USD)VRBO
From $287 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 $287 per night (USD)Expedia
From $129 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 $129 per night (USD)VRBO
From $760 per night (USD)VRBO
LVCC Villa Green Adventure
- Bedrooms:
- 4
- 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 $492 per night (USD)VRBO
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 completed in October, 2020 and located right on Rum Road; walking ...
From $492 per night (USD)VRBO
From $784 per night (USD)VRBO
Beachy Keen, newly constructed pool home near beach
- Bedrooms:
- 2
- 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 $784 per night (USD)VRBO
From $338 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 $338 per night (USD)VRBO
From $1477 per night (USD)Expedia
BEACHFRONT, HEATED POOL, KAYAKS/SUP, LANAI W/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
* ALWAYS CLEANED AND SANITIZED BY A PROFESSIONAL CLEANING SERVICE!! Welcome to North Captiva Island, a private, bridge-l ...
From $1477 per night (USD)Expedia
From $158 per night (USD)VRBO
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 $158 per night (USD)VRBO
From $488 per night (USD)Expedia
Endless Summer - In Search of the Perfect House in North Captiva, sleeps 10.
- Bedrooms:
- 2
- 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 $488 per night (USD)Expedia
From $458 per night (USD)VRBO
2B/2B Private Heated Pool, Golf Cart, Club Access, Games,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Thank you for your interest in Magic Po'Cean and North Captiva Island. Leave your car (and your cares) at The Island Cl ...
From $458 per night (USD)VRBO
From $116 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 $116 per night (USD)VRBO
From $282 per night (USD)VRBO
Come spend some island time at Reel Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $282 per night (USD)VRBO
From $328 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 $328 per night (USD)VRBO
From $246 per night (USD)VRBO
☀️TRANQUILITY VILLA☀️
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $246 per night (USD)VRBO
From $593 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 $593 per night (USD)VRBO
From $402 per night (USD)VRBO
North Captiva Island Beach House/60 Second Walk to 4 Miles of Awesome Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***** NEW GOLF CART WITH RENTAL***** Winterhaven 4550 Oyster Shell Drive North Captiva Island, Florida NORTH CAP ...
From $402 per night (USD)VRBO
From $815 per night (USD)Expedia
Peace of Paradise: Private Pool, Optional NCI Club
- 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 $815 per night (USD)Expedia
From $867 per night (USD)VRBO
Summer Specials! Luxury Beach House, Private Pool, 2 golf carts
- Bedrooms:
- 2
- 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 $867 per night (USD)VRBO
From $880 per night (USD)Expedia
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 $880 per night (USD)Expedia
From $115 per night (USD)VRBO
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 ...
From $115 per night (USD)VRBO
From $697 per night (USD)VRBO
All Conched Out - Luxe 3 Br, Private pool, outdoor pool table - pets considered
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
All Conched Out This adorable “pink palace” retreat has everything you need for a fun, wonderful and relaxing vacation ...
From $697 per night (USD)VRBO
From $268 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 $268 per night (USD)VRBO
From $365 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 $365 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 $318 per night (USD)VRBO
LUXURY ISLAND RENTAL/CLUB w/POOL, KAYAKS, 3BR PRIV BEACH ACCESS, BOAT DOCK AVAIL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FANTASTIC NEW LUXURY ISLAND RENTAL! OPEN and WELCOMING GUESTS! ONE 6 PERSON GOLF CART INCLUDED COMPLIMENTARY AS AVAILABL ...
From $318 per night (USD)VRBO
From $246 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 $246 per night (USD)VRBO
From $257 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 $257 per night (USD)VRBO
From $146 per night (USD)VRBO
Serenity Bay Studio #3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In addition to the Big House on our property, we have a 4-plex, with four studio apartments. Two face the water, two fa ...
From $146 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 $115 per night (USD)VRBO
Price drop for last-minute bookings - your perfect break!
- 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 $115 per night (USD)VRBO
From $399 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 $399 per night (USD)Expedia
From $1152 per night (USD)VRBO
Serendipity is BACK - Complete remodel April 2024 - Pool; 2 Golf Carts
- Bedrooms:
- 3
- 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 $1152 per night (USD)VRBO
From $312 per night (USD)VRBO
Remodeled 4/2 on quiet canal with 10k boatlift, 5 mins to Charlotte Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful and quiet waterfront home with amazing view and great fishing. The master bath was a focus point on this house ...
From $312 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:
- 3
- 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 $178 per night (USD)VRBO
Cottage with private deck in the heart of Matlacha
- Bedrooms:
- 1
- 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 $178 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:
- 1
- 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 $171 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 $171 per night (USD)VRBO
From $916 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 $916 per night (USD)Expedia
From $808 per night (USD)VRBO
Bluefin Beach House, Luxury Home with Pool & Spa on North Captiva, 2 Golf Carts
- Bedrooms:
- 4
- 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 $808 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:
- 0
- 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 $158 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 $158 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)Expedia
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)Expedia
From $240 per night (USD)VRBO
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 $240 per night (USD)VRBO
From $1094 per night (USD)Expedia
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 18
Overview of the property: • No Worries Atoll is a stunning 3,300 square foot pool home. $1.5 million extensive renovati ...
From $1094 per night (USD)Expedia
From $175 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 $175 per night (USD)VRBO
From $897 per night (USD)VRBO
AWESOME HUGE BEACH HOUSE GREAT FLOOR PLAN VIEWS UPDATES CLUB!2 CARTS PETS
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
RUFF LIFE is a WOW Beach Vacation Rental! Tropical Ruff Life Beach House is Amenity Packed! It is a Truly Fantastic, L ...
From $897 per night (USD)VRBO
From $238 per night (USD)VRBO
Hurricane Ian update Roofs are on pools are heated life rolls on Thank God
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Beautifully upgraded yet very comfortable condo it the best fishing spot! Over looking the pool and watet inlet. Enjoy t ...
From $238 per night (USD)VRBO
From $154 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 $154 per night (USD)VRBO
From $1026 per night (USD)VRBO
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Since 2017, "The Blue Marlin" has provided sea-loving families with the ultimate North Captiva beachfront retreat. This ...
From $1026 per night (USD)VRBO
From $844 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 $844 per night (USD)Expedia
From $115 per night (USD)VRBO
Price drop for last-minute bookings - your perfect break!
- 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 $115 per night (USD)VRBO
From $149 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 $149 per night (USD)VRBO
From $563 per night (USD)VRBO
Private Elevated Pool & Deck!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to North Captiva Island! A short, ferry ride separates you from reality, for your tropical paradise vacation. A ...
From $563 per night (USD)VRBO
From $855 per night (USD)VRBO
Private Pool Home Spectacular Sunsets Steps from the Beaches & StarLink Internet
- Bedrooms:
- 2
- 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 ...
From $855 per night (USD)VRBO
From $354 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 $354 per night (USD)VRBO
From $325 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 $325 per night (USD)VRBO
From $350 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 $350 per night (USD)VRBO
From $166 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 $166 per night (USD)Expedia
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 $79 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 $79 per night (USD)VRBO
From $564 per night (USD)VRBO
NOW OPEN, SHC private lakefront,minutes to gulf, with STARLINK HiSpeed Internet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Second Star is a peaceful place with a state-of-the-art interior, a unique 3 bedroom, 2 bath, 1450 sf home, nestled in p ...
From $564 per night (USD)VRBO
From $248 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 $248 per night (USD)Expedia
From $207 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 $207 per night (USD)VRBO
From $526 per night (USD)Expedia
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home
- Bedrooms:
- 2
- 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 $526 per night (USD)Expedia
From $387 per night (USD)VRBO
Spectacular Nature! Waterfront! Prime Fishing! Bring Boat, 2 Free Kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical paradise that can't be beat! Incredible views! Taking reservations for 2025. No hurricane damage. Fishing enthu ...
From $387 per night (USD)VRBO
From $821 per night (USD)Expedia
EXCLUSIVE AT THE BEACH: 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 Large, 5-bedro ...
From $821 per night (USD)Expedia
From $352 per night (USD)VRBO
Rockstar Beach House North Captiva Island, 25’ boat slip, NCIC pools, golf cart
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*NORTH CAPTIVA AND THIS HOUSE ARE ONLY ACCESSIBLE BY FERRY BOAT. ...
From $352 per night (USD)VRBO
![☀︎🏝⛱︎ Beachfront Elegance⛱︎🏝☀︎ \n[2025 Spring + Summer Weeks Available Now!]](https://media.vrbo.com/lodging/19000000/18770000/18767200/18767197/c4e76946.jpg?impolicy=ccrop&w=350&h=233&q=medium)
From $723 per night (USD)Expedia
☀︎🏝⛱︎ Beachfront Elegance⛱︎🏝☀︎ \n[2025 Spring + Summer Weeks Available Now!]
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Our unique, fully renovated island home is 75 steps from the beach with spectacular panoramic views. Spring -> Summer ...
From $723 per night (USD)Expedia
From $500 per night (USD)VRBO
Island Oasis/Hidden Beach House-Private pool
- Bedrooms:
- 2
- 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 $500 per night (USD)VRBO
From $467 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 $467 per night (USD)Expedia
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 $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
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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 $188 per night (USD)Expedia
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 $188 per night (USD)Expedia
From $441 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 $441 per night (USD)VRBO
From $115 per night (USD)Expedia
Price drop for last-minute bookings - your perfect break!
- 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 $115 per night (USD)Expedia
From $709 per night (USD)VRBO
BEACH FRONT with the best sunsets on the island!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Newly remodeled, ON THE BEACH! OCEAN FRONT HOME ON PRISTINE SANDY WHITE BEACHES Spectacular views, best sunsets! WE ar ...
From $709 per night (USD)VRBO
From $910 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 $910 per night (USD)VRBO
From $544 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 $544 per night (USD)VRBO
From $845 per night (USD)Expedia
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 $845 per night (USD)Expedia
From $617 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 preserve on both sides—secluded, serene, and truly privat ...
From $617 per night (USD)VRBO
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 $635 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 $635 per night (USD)VRBO
From $335 per night (USD)Expedia
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 $335 per night (USD)Expedia