Book Holiday Homes in Gasparilla Island

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Featured Holiday Homes in Gasparilla Island

WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!

WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!

Englewood FL
When you stay at this vacation home in Englewood, you'll be on the beach, within a 5-minute walk of Englewood Beach and Lemon Bay.
Opens in a new windowWOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!
COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more

COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more

Englewood FL
When you stay at this vacation home in Englewood, you'll be near the beach, within a 5-minute walk of Englewood Beach and Lemon Bay.
Opens in a new windowCOCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more
Cape Heaven, heated pool, and volleyball court, and park.

Cape Heaven, heated pool, and volleyball court, and park.

Cape Coral FL
With a stay at this vacation home in Cape Coral (Mariner), you'll be within a 10-minute drive of Cape Coral Sports Complex and Fellowship Park.
Opens in a new windowCape Heaven, heated pool, and volleyball court, and park.
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Canal fun! Boat, Pool, Hot tub, Bikes & Kayaks

Canal fun! Boat, Pool, Hot tub, Bikes & Kayaks

Cape Coral FL
With a stay at this vacation home in Cape Coral (Pelican), you'll be within a 15-minute drive of Rotary Park Environmental Center and Glover Bight Trail.
Opens in a new windowCanal fun! Boat, Pool, Hot tub, Bikes & Kayaks
Ultra Modern Home w Heated Salt water Pool pet friendly

Ultra Modern Home w Heated Salt water Pool pet friendly

Cape Coral FL
The price is AU$620 per night from 25 May to 26 May
AU$620
25 May - 26 May
includes taxes & fees
With a stay at this vacation home in Cape Coral (Mariner), you'll be within a 10-minute drive of Cape Coral Sports Complex and Fellowship Park.
Opens in a new windowUltra Modern Home w Heated Salt water Pool pet friendly
Big on the Beach House  6BR Home + Club Access, Private Dock & Stunning Views

Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views

Captiva FL
With a stay at this vacation home in Captiva (North Captiva), you'll be steps from North Captiva Island Beach.
Opens in a new windowBig on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views
New luxury pool home, 2 min to beach, 360 water views, club available

New luxury pool home, 2 min to beach, 360 water views, club available

North Captiva FL
With a stay at this vacation home in Captiva (North Captiva), you'll be 6 minutes by foot from North Captiva Island Beach.
Opens in a new windowNew luxury pool home, 2 min to beach, 360 water views, club available
Private Beach Access Steps Away,  Pool, Outdoor Bar, 2 Golf Carts, 360 Views.

Private Beach Access Steps Away, Pool, Outdoor Bar, 2 Golf Carts, 360 Views.

Captiva FL
With a stay at this vacation home in Captiva (North Captiva), you'll be close to North Captiva Island Beach and Cayo Costa Beaches.
Opens in a new windowPrivate Beach Access Steps Away, Pool, Outdoor Bar, 2 Golf Carts, 360 Views.
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 FL
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.
Opens in a new window120 steps to beach! Safely on the beach side of the road!
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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
1229 Holiday Homes
Lowest Price
AU$285
Highest Price
AU$818
Popular accommodation
WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!, COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more, Cape Heaven, heated pool, and volleyball court, and park., Canal fun! Boat, Pool, Hot tub, Bikes & Kayaks, Ultra Modern Home w Heated Salt water Pool pet friendly, Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views, New luxury pool home, 2 min to beach, 360 water views, club available, Private Beach Access Steps Away, Pool, Outdoor Bar, 2 Golf Carts, 360 Views., 120 steps to beach! Safely on the beach side of the road!

Top trending hotels in Gasparilla Island

Boca Grande Hotel

Boca Grande Hotel

2.5 out of 5
5800 Gasparilla Road Boca Grande FL
Fully refundableReserve now, pay when you stay
The price is AU$302 per night from 17 May to 18 May
AU$302
17 May - 18 May
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.
Opens in a new windowBoca Grande Hotel
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is AU$285 per night from 25 May to 26 May
AU$285
25 May - 26 May
includes taxes & fees
When you stay at Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton in Punta Gorda, you'll be next to a golf course, within a 5-minute drive of Fishermen's ...
Opens in a new windowSunseeker Resort Florida Gulf Coast, Curio Collection Hilton
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is AU$295 per night from 9 June to 10 June
AU$295
9 June - 10 June
includes taxes & fees
With a stay at The Suites at Fishermen’s Village- 2 Bedroom Suites in Punta Gorda (Punta Gorda Isles), you'll be steps from Peace River and Military Heritage ...
Opens in a new windowThe Suites at Fishermen’s Village- 2 Bedroom Suites
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South Seas

South Seas

3.5 out of 5
5400 South Seas Plantation Rd Captiva FL
The price is AU$818 per night from 17 May to 18 May
AU$818
17 May - 18 May
includes taxes & fees
With a stay at South Seas in Captiva, you'll be within a 10-minute walk of Alison Hagerup Beach Park and Jungle Drums.
Opens in a new windowSouth Seas
Don't see what you're looking for?
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.

Top Picks

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^Subject to availability and chosen travel dates.