Book Holiday Homes in Gasparilla Island

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Featured Holiday Homes in Gasparilla Island

4-Bedroom Pool Home Convenient To Beaches

4-Bedroom Pool Home Convenient To Beaches

Venice
With a stay at this vacation home in Venice (South Venice), you'll be within a 15-minute drive of Venice Beach and Nokomis Beach.
4-Bedroom Pool Home Convenient To Beaches
South Seas Bayside Villa 5130: Your Perfect Island Retreat

South Seas Bayside Villa 5130: Your Perfect Island Retreat

Captiva
Located in Captiva, this vacation home is by the sea, within a 15-minute walk of Alison Hagerup Beach Park and Jungle Drums.
South Seas Bayside Villa 5130: Your Perfect Island Retreat
120 steps to beach!  Safely on the beach side of the road!

120 steps to beach! Safely on the beach side of the road!

Englewood
With a stay at this vacation home, you'll be centrally located in Englewood, steps from Englewood Beach and 3 minutes by foot from Lemon Bay.
120 steps to beach! Safely on the beach side of the road!
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PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

Cape Coral
With a stay at this vacation home in Cape Coral (Trafalgar), you'll be within a 5-minute drive of Palmetto-Pine Country Club and Cape Coral Sports Complex.
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY

INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY

Punta Gorda
With a stay at this vacation home in Punta Gorda (Burnt Store Isles), you'll be a 3-minute drive from Charlotte Harbor Preserve State Park and 5 minutes from ...
INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY
Manasota Key Dream Beach House

Manasota Key Dream Beach House

Englewood
With a stay at this vacation home in Englewood, you'll be by the sea, within a 15-minute drive of Englewood Beach and Lemon Bay.
Manasota Key Dream Beach House
South Seas Beach Villa 2418 Coastal Luxury

South Seas Beach Villa 2418 Coastal Luxury

Captiva
When you stay at this vacation home in Captiva, you'll be on the beach, within a 15-minute walk of Alison Hagerup Beach Park and Jungle Drums.
South Seas Beach Villa 2418 Coastal Luxury
Walk to Beach, Pool+Hot Tub, Game Room | Captiva 5BDR | Coco Mango by AvantStay

Walk to Beach, Pool+Hot Tub, Game Room | Captiva 5BDR | Coco Mango by AvantStay

Captiva
When you stay at this vacation home in Captiva, you'll be by the sea, within a 10-minute walk of McCarthy's Marina and Captiva Beach.
Walk to Beach, Pool+Hot Tub, Game Room | Captiva 5BDR | Coco Mango by AvantStay
4-bedroom Screened in Pool House with Bar!  Golf Carts, Roof Top, and Amenities!

4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!

North Captiva Island
With a stay at this vacation home in Captiva (North Captiva), you'll be convenient to North Captiva Island Beach.
4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Gasparilla Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gasparilla Island vacation homes are the perfect way for you to wing it.

Holiday houses in Gasparilla Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gasparilla Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gasparilla Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gasparilla Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gasparilla Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gasparilla Island Holiday Homes essential information

Accommodation
1299 Holiday Homes
Lowest Price
AU$100
Highest Price
AU$343
Popular accommodation
4-Bedroom Pool Home Convenient To Beaches, South Seas Bayside Villa 5130: Your Perfect Island Retreat, 120 steps to beach! Safely on the beach side of the road!, PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!, INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY, Manasota Key Dream Beach House, South Seas Beach Villa 2418 Coastal Luxury, Walk to Beach, Pool+Hot Tub, Game Room | Captiva 5BDR | Coco Mango by AvantStay, 4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!

Top trending hotels in Gasparilla Island

Boca Grande Hotel

Boca Grande Hotel

2.5 out of 5
5800 Gasparilla Road, Gasparilla Island, Boca Grande, FL
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 14 Sept to 15 Sept
AU$209
14 Sept - 15 Sept
includes taxes & fees
Located in Boca Grande, Boca Grande Hotel is a 1-minute drive from Uncle Henrys Marina and 5 minutes from Gasparilla Marina.
Boca Grande Hotel
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is AU$343 per night from 2 Sept to 3 Sept
AU$343
2 Sept - 3 Sept
includes taxes & fees
When you stay at Sunseeker Resort Charlotte Harbor in Punta Gorda, you'll be next to a golf course, within a 5-minute drive of Fishermen's Village and Military ...
Sunseeker Resort Charlotte Harbor
Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

2.5 out of 5
4056 Tamiami Trl, Port Charlotte, FL
Fully refundableReserve now, pay when you stay
The price is AU$100 per night from 18 Aug to 19 Aug
AU$100
18 Aug - 19 Aug
includes taxes & fees
A stay at Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda places you in the heart of Port Charlotte, within a 5-minute drive of Bayshore Park Fishing ...
Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda
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Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
1941 Tamiami Trl, Port Charlotte, FL
Fully refundableReserve now, pay when you stay
The price is AU$112 per night from 25 Aug to 26 Aug
AU$112
25 Aug - 26 Aug
includes taxes & fees
Located in Port Charlotte, Days Inn by Wyndham Port Charlotte/Punta Gorda is a 2-minute drive from Port Charlotte Town Center and 6 minutes from Charlotte Sports ...
Days Inn by Wyndham Port Charlotte/Punta Gorda
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See all available properties in Gasparilla Island
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.