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North Captiva Island, Florida Vacation Rentals

148 listings found
About North Captiva Island, Florida

The private wonder of a remote tropical island with the modern luxuries of a high-end vacation—that is what awaits you at North Captiva Island resort. Famous for its five miles of sandy white beaches that are literally covered with ornate seashells from the ocean’s depth, your North Captiva Island vacation takes you to a most wondrous place. Secluded, remote and bordering a 700-acre state land reserve, the beaches of North Captiva Island resort are some of the most private and unpopulated along the Florida coast.

One of the most exciting parts of your North Captiva Island condo rental is how you make your entrance on the island! Part of the charm of its remote location is that North Captiva Island resort is only accessible by ferryboat or private planes.  You will feel like a celebrity coming to your private oasis as you settle into your North Captiva island condominium or your very own vacation house in North Captiva Island.

Historic Legends Surround Your North Captiva Island Rental

With a rich history that includes original occupation by the fierce Calusa Indian tribe, your North Captiva Island house rental is surrounded by legends of yesterday.  Over many generations, the island has been populated by gold seeking Spaniards and pirates seeking refuge from the seas. In fact, legend has it that Jose Gaspar, a pirate infamous for imprisoning captives on the island, was the inspiration for the island’s name.

Natural Beauty Surrounds Your North Captiva Island Rental

With such unspoiled beaches, a North Captiva Island rental is ideal for the serious shell collector. Whether combing for the perfect shell on the barrier island of Cayo Costa or discovering an oceanic treasure right near your very own North Captiva Island house rental, you will find keepsakes that will last a lifetime. A North Captiva vacation also allows you the opportunity to explore the amazing natural wonder on the island’s preserve. Near most all North Captiva vacation rentals, you can also indulge in nature and history cruises.

North Captiva Island Rental Includes Outdoor Sporting Adventure

Taking full advantage of your natural surroundings near your North Captiva Island rental, you and your family can indulge in a wide array of recreational fun on the island. From snorkeling to fishing and diving, a vacation house in North Captiva Island gives you endless opportunities for water sports. The beauty of the island is also a wondrous sight from any chartered boat excursion, with many tours available for fishing, nature and sunset cruises—a perfect way to view the beauty of North Captiva island resort.

Every Condominium in North Captiva Island Close to Aquatic Wonders

Close on the shoreline of your vacation house in North Captiva Island or your North Captiva Island condo, you can be part of nature and swim in close proximity to dolphins, sea otters and manatees. Or if you want to dive a bit deeper, certified SCUBA diving enthusiasts can discover the artificial reef of the Gulf of Mexico, just one of the many oceanic experiences that come with a North Captiva Island condo rental.

North Captiva Island Condo and House Rentals Provide Peaceful Retreat

Even though it has garnered a reputation for its low-key lifestyle, your North Captiva vacation rental is near several gourmet restaurants as well as an island grocer that provides everything you need. For the romantic couple or group gatherings, you can pick up anything you need at a local grocer and plan the perfect cookout right in front of your condominium in North Captiva Island or your very own North Captiva Island house rental. With natural landscapes, unspoiled beauty and one of the most pristine beaches anywhere in Florida, North Captiva Island is the resort vacation of a lifetime.

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Rate & Availability Disclaimer
Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.

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Orchid Estates

Cozy 2BR Florida Home Near the Shore!

King Bed & Patio, Minutes to the Beach

Turtle Bay Hideaway | Large Pet Friendly Home on Siesta Key w/ Private Pool & Spa, Beach Access

Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!

Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach

Sandy Rocks | Ultimate Bundle: 2 Private Pet Friendly Homes, 2 Private Heated Pools, Walk to Beach!

Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Crescent Cottage | Private Pool, Lounging Area, Short Walk to Crescent Beach

Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!

Fiesta Playa | Luxury Home on Siesta Key w/ Private Elevator, 2 Minute Walk to Crescent Beach!

Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!

Casa Coquina | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Conch | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Antilles | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Eulimia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Junonia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Abalone | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Stolida | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Nautilus | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Tegula | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Sandpiper Cottage | Pet Friendly Home in Sarasota w/ Private Pool, 2 Story Loft, Close to Siesta Key

New Listing | Gulf Birdie | Waterfront Home on Siesta Key, w/ Private Heated Pool & Hot Tub!

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach

Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!

Beach Dream | Home w/ Ocean Views, 2 Private Pools, & Rooftop Lookout! Steps to Siesta Key Beach

Silver Shore | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Crystal Sands | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Beach Palm Villa | Private Heated Pool, Fire Pit, & Spacious Outdoor Lounging Area

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!

Casa De Mariposa | Ocean Views, Spacious Balcony, Private Heated Pool, & Steps to Siesta Key Beach!

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Seaside Cottage | Pet Friendly Siesta Key Home w/ Private Pool, Across From Beach Access 9!

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

New Listing! Avanti Villa | Hot Tub, Walk to Siesta Beach and Village, Beach Views

Endless Views | Walking Distance To Siesta Key Beach + Village, Panoramic Views

The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!

Beach Walk Cottage | Pet Friendly Home on Palm Island, Private Pool, Ping Pong Table, Walk to Beach!

Seas the Day | Canal Front Home on Siesta Key w/ Private Heated Pool & Kayaks, Walk to Beach!

Isla Amor | Waterfront Home on Siesta Key w/ Private Heated Pool, Fire Pit, Walk to Beach!

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

New Listing! Don't Be Salty | Gorgeous Modern Home w/ Private Heated Pool & Spa, Near Beach!

The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village

Sophie's Cottage | Pet Friendly, Waterfront Home w/ Private Pool & Kayaks! Beach & Village Close!

Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!

Sophie's Quartier | Siesta Bundle, 2 Pet Friendly Waterfront Homes w/ 2 Private Pools, Near Village

Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Siesta Salt Life | Walking Distance to Siesta Key Beach & Village w/ Private Heated Pool!

Sea la Vie | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

The Palms Cottage | Pet Friendly Home w/ Private Pool & Spa, Walking Distance to Siesta Key Beach!

Caribbean Dream | Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

Siesta Villa | Luxury Condo in Siesta Village w/ Heated Pool, Walking Distance to Beach & Village!

Siesta Breeze Retreat | Walk to Beach, Siesta Village, Shared Pool!

At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!

Vinca | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Honeysuckle | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Plumbago | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Lantana | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mimosa | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

The Hummingbird | Pet Friendly Home Located in Siesta Key Village w/ Private Pool, Walk to Beach!

New Listing | Pet Friendly Home on Siesta Key w/ Outdoor Patio & Private Screened-In Heated Pool!

Casa Ohana | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

The Big Kahuna | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, Steps to Beach & Village!

Casa Mahalo | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

New Listing! The Birdhouse | Private Siesta Key Home w/ Heated Pool, Minutes Away From Beach!

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Coral Reef! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Bali Hai House | Luxury Waterfront Home on Siesta Key w/ Large Private Heated Pool & Outdoor Patio!

Blu Sky Cottage | Pet Friendly, Canal Front Home on Siesta Key w/ Private Heated Pool & Spa, Kayaks!

Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area

Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!

New Listing! Sunburst Courtyard | Pet Friendly Waterfront Home, Walk to Siesta Key Beach & Village!

New Listing! Island Sol | Private Pool, Pet Friendly, Minutes from Siesta Beach

Luna Flores | Pet Friendly Home in Sarasota w/ 2 Private Heated Pools & Screened-In Porches

Villa Las Flores | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Luna Nueva | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!

Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space

The Pearl on the Bay | Luxury Water Front Home Near Siesta Key, Gorgeous Views & Private Pool!

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

New Listing! Siesta Dolce | Luxury Siesta Key Home w/ Private Heated Pool, Close To Beach!

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Lush Landscaping

Ocean Sky | Pet Friendly Home in Sarasota w/ Private Heated Pool & Fire Pit!

Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach

Baydream Bungalow | Pet Friendly Home w/ Private Heated Screened-In Pool

Casa Leone | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Putting Green!

Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

Floritas Key | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

New Listing! Mermaids Oasis | Private Pool, 5 Minute Walk to St. Armands Circle!

Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!

New Listing! Manatee Cove | Waterfront Home on Lido Key, 30 Second Walk to St. Armands Circle!

Sunset Heaven | St Armands - Lido Key Home w/ Water Views, Dock Access, Private Heated Pool & Spa!

Florida Retreat Nr Lakewood Ranch Sports Campus

New Listing! | Front Row Seat | Luxury Beachfront Home Located On Anna Maria Island!

New Listing! | Beach a la Mode | Luxury Canal Front Home on Anna Maria Island!