Vacation Rentals in Captiva, Florida

50 Properties Available

Drip Castle Estates Captiva Island - 20 Bedroom Estate Rentals for Large Groups! Villa
Drip Castle Estates Captiva Island - 20 Bedroom Estate Rentals for Large Groups!
$19139 / night
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Bring the Family! Beachfront Estate, Private Pool+Spa, 9 Bedrooms, Sleeps 30 Private vacation home
Bring the Family! Beachfront Estate, Private Pool+Spa, 9 Bedrooms, Sleeps 30
$9601 / night
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Beachfront Paradise - Directly On The Beach! Private vacation home
Beachfront Paradise - Directly On The Beach!
$3149 / night
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Get Ready for Adventures! 3 Elegant Villa Units, Pools, Beach Access, Restaurant Apartment
Get Ready for Adventures! 3 Elegant Villa Units, Pools, Beach Access, Restaurant
$2732 / night
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Sunset View Beach Home with Full Resort Access Private vacation home
Sunset View Beach Home with Full Resort Access
$2625 / night
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2 Spacious Villas, Free Parking, Beach and Pool Apartment
2 Spacious Villas, Free Parking, Beach and Pool
$2423 / night
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Dolphin Cove - Captiva Luxury Escape Private vacation home
Dolphin Cove - Captiva Luxury Escape
$2417 / night
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Unparalleled Gulf-to-Bay Living - Luxury Beachfront Retreat-Captiva Island Private vacation home
Unparalleled Gulf-to-Bay Living - Luxury Beachfront Retreat-Captiva Island
$1893 / night
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Your Home Away From Home! 2 Family-friendly Villas, Access to Tennis Court! Apartment
Your Home Away From Home! 2 Family-friendly Villas, Access to Tennis Court!
$1871 / night
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Get Ready for Adventures! 2 Elegant Villa Units, Pools, Beach Access, Restaurant Apartment
Get Ready for Adventures! 2 Elegant Villa Units, Pools, Beach Access, Restaurant
$1822 / night
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Coastal Villa With Panoramic Gulf & Pass Views Private vacation home
Coastal Villa With Panoramic Gulf & Pass Views
$1633 / night
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ANDY ROSSE LUXURY VILLA - WALK TO BEACH, SHOPS & RESTAURANTS Private vacation home
ANDY ROSSE LUXURY VILLA - WALK TO BEACH, SHOPS & RESTAURANTS
$1606 / night
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Villa Del Mar - The ultimate vacation home now reduced for 2024! Private vacation home
Villa Del Mar - The ultimate vacation home now reduced for 2024!
$1384 / night
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Captiva's Finest Multi-Generation Consistent 5-Star Vacation Home! Private vacation home
Captiva's Finest Multi-Generation Consistent 5-Star Vacation Home!
$1367 / night
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Stunning Captiva Vacation Rental - Bella Vita Private vacation home
Stunning Captiva Vacation Rental - Bella Vita
$1279 / night
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South Seas Beach Home 3 Private vacation home
South Seas Beach Home 3
$1260 / night
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4BR Beachfront North Captiva Home with Golf Cart Private vacation home
4BR Beachfront North Captiva Home with Golf Cart
$1232 / night
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Villa Elena-Paradise on Captiva Island with private pool and beach access Private vacation home
Villa Elena-Paradise on Captiva Island with private pool and beach access
$1227 / night
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Sandrift 1071 Captiva`s Premier Gulf-Front Escape: 3BR/3.5BA Retreat with Condo
Sandrift 1071 Captiva`s Premier Gulf-Front Escape: 3BR/3.5BA Retreat with
$1137 / night
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The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock Private vacation home
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
$1130 / night
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Captiva Village Home Private vacation home
Captiva Village Home
$1095 / night
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NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN Private vacation home
NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN
$1082 / night
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South Seas Resort | 2BR Land's End Water Villa Condo
South Seas Resort | 2BR Land's End Water Villa
$951 / night
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Private Island Luxury * Pool * Dock * Club Access Private vacation home
Private Island Luxury * Pool * Dock * Club Access
$947 / night
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South Seas Beach Villa 2028 - Gulf front largest floor plan Private vacation home
South Seas Beach Villa 2028 - Gulf front largest floor plan
$931 / night
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VILLA IN THE AIR - 2 Golf Carts, Private Pool, Steps to the beach Private vacation home
VILLA IN THE AIR - 2 Golf Carts, Private Pool, Steps to the beach
$929 / night
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Sanderella- Ocean Front Vacation Home w\/ Large Private Beach Private vacation home
Sanderella- Ocean Front Vacation Home w\/ Large Private Beach
$924 / night
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Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool Private vacation home
Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool
$900 / night
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South Seas Lands End 1610 Private vacation home
South Seas Lands End 1610
$866 / night
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FULL renovation ongoing. 4 bedroom\/3 bath. Ready for July 2024 rentals. Private vacation home
FULL renovation ongoing. 4 bedroom\/3 bath. Ready for July 2024 rentals.
$847 / night
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Beachfront Secluded Sunset Sanctuary with Panoramic Views Private vacation home
Beachfront Secluded Sunset Sanctuary with Panoramic Views
$833 / night
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Best Views & Beach on Captiva - Jensen's “On the Gulf” - Casual Lux - South Beach Suite 3 Hotel resort
Best Views & Beach on Captiva - Jensen's “On the Gulf” - Casual Lux - South Beach Suite 3
$826 / night
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New to the rental program! Book your week today! Condo
New to the rental program! Book your week today!
$810 / night
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Beach Front, South Seas Beach Villa 2111 Private vacation home
Beach Front, South Seas Beach Villa 2111
$806 / night
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Triple Tales - Waterfront Property with Dock, Private pool & 2 minutes to beach! Private vacation home
Triple Tales - Waterfront Property with Dock, Private pool & 2 minutes to beach!
$803 / night
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Private & Spacious [2300sqft] home w/Pool,Hot Tub,Golf Cart, Pet Friendly & Club Private vacation home
Private & Spacious [2300sqft] home w/Pool,Hot Tub,Golf Cart, Pet Friendly & Club
$792 / night
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Stunning Captiva Home-Centrally Located- Steps to the Beach Private vacation home
Stunning Captiva Home-Centrally Located- Steps to the Beach
$792 / night
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Ocean views, sleeps 10, heated pool, 2 golf carts Private vacation home
Ocean views, sleeps 10, heated pool, 2 golf carts
$786 / night
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Solitude North Captiva 2 Carts, Dock, Private Pool, Club, Sleeps 12 Private vacation home
Solitude North Captiva 2 Carts, Dock, Private Pool, Club, Sleeps 12
$776 / night
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Beach Villa 2004 -Sublime Gulf Beach Villa Condo
Beach Villa 2004 -Sublime Gulf Beach Villa
$771 / night
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Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week Private vacation home
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
$765 / night
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Silverseas Cottage: Cozy 3BR Fall Retreat - Private Pool, Beach Access, 2 Carts Private vacation home
Silverseas Cottage: Cozy 3BR Fall Retreat - Private Pool, Beach Access, 2 Carts
$762 / night
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Five bedroom Channel Front Estate home on Captiva! Perfect for Family & Friends Private vacation home
Five bedroom Channel Front Estate home on Captiva! Perfect for Family & Friends
$756 / night
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SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access Private vacation home
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
$750 / night
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Beach House 29 Captiva Island beach view resort home Private vacation home
Beach House 29 Captiva Island beach view resort home
$749 / night
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SALTY SMUGGLER - 4 Bed, 3 Bath, Sleeps 12, Large Private Pool, 2 Golf Carts Private vacation home
SALTY SMUGGLER - 4 Bed, 3 Bath, Sleeps 12, Large Private Pool, 2 Golf Carts
$741 / night
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The Wicked Dolphins - Home with Private Pool & Golf Cart- Sunset Cruise & Ferry Tickets Included! Private vacation home
The Wicked Dolphins - Home with Private Pool & Golf Cart- Sunset Cruise & Ferry Tickets Included!
$737 / night
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Paradise 3-BR 2-BA steps to the beach, private pool surrounded by nature! Private vacation home
Paradise 3-BR 2-BA steps to the beach, private pool surrounded by nature!
$734 / night
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Wait and Sea! Now Reduced for Oct until Christmas week 2024! Amazing location! Private vacation home
Wait and Sea! Now Reduced for Oct until Christmas week 2024! Amazing location!
$728 / night
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Endless Summer - In Search of the Perfect House in North Captiva, sleeps 10. Private vacation home
Endless Summer - In Search of the Perfect House in North Captiva, sleeps 10.
$724 / night
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