Book Holiday Homes in Gasparilla Island

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Gasparilla Island

Single family pool home in a quiet neighborhood, close to five beaches,

Single family pool home in a quiet neighborhood, close to five beaches,

Port Charlotte FL
With a stay at this vacation home in Port Charlotte (Gulf Cove), you'll be within a 10-minute drive of Cape Haze Pioneer Trail Park and Oyster Creek Golf ...
Opens in a new windowSingle family pool home in a quiet neighborhood, close to five beaches,
WATERFRONT LUXURY PRIVATE HEATED POOL&SPA/MIN TO BEACH/DOCK&LIFT/GULF ACCESS

WATERFRONT LUXURY PRIVATE HEATED POOL&SPA/MIN TO BEACH/DOCK&LIFT/GULF ACCESS

Port Charlotte FL
With a stay at this vacation home in Port Charlotte (South Gulf Cove), you'll be within a 15-minute drive of Cape Haze Pioneer Trail Park and Gasparilla ...
Opens in a new windowWATERFRONT LUXURY PRIVATE HEATED POOL&SPA/MIN TO BEACH/DOCK&LIFT/GULF ACCESS
Tiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time

Tiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time

Bokeelia FL
With a stay at this vacation home in Bokeelia, you'll be within a 5-minute drive of Randell Research Center and Calusa Heritage Trail.
Opens in a new windowTiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time
Save an average of 15% on thousands of hotels when you're signed in
Charming 2-bedroom beach themed Englewood house with heated pool and large yard.

Charming 2-bedroom beach themed Englewood house with heated pool and large yard.

Englewood FL
With a stay at Charming 2-bedroom beach themed Englewood house with heated pool and large yard. in Englewood (Olde Englewood Village), you'll be within a 15-minute ...
Opens in a new windowCharming 2-bedroom beach themed Englewood house with heated pool and large yard.
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
Waterfront Retreat: Fish, Kayak, and Paddle Board  on Property + Pool + Hottub

Waterfront Retreat: Fish, Kayak, and Paddle Board on Property + Pool + Hottub

Englewood FL
With a stay at this vacation home in Placida (Palm Island), you'll be a 1-minute drive from Lemon Bay and 8 minutes from Stump Pass Beach State Park.
Opens in a new windowWaterfront Retreat: Fish, Kayak, and Paddle Board on Property + Pool + Hottub
Lakefront Exquisite Home in Placida Sands,
A Fishing and Wildlife Phenomenon

Lakefront Exquisite Home in Placida Sands, A Fishing and Wildlife Phenomenon

Placida FL
With a stay at this vacation home in Port Charlotte (Rotonda Sands), you'll be within a 10-minute drive of Gasparilla Marina and Cape Haze Pioneer Trail ...
Opens in a new windowLakefront Exquisite Home in Placida Sands, A Fishing and Wildlife Phenomenon
Spacious 4-bedroom, harbor Acces ON canal, fish of the dock Rv parking POOL SPA

Spacious 4-bedroom, harbor Acces ON canal, fish of the dock Rv parking POOL SPA

Port Charlotte FL
Located in Port Charlotte (Edgewater), this vacation home is within a 15-minute walk of Peace River and Port Charlotte Beach Park.
Opens in a new windowSpacious 4-bedroom, harbor Acces ON canal, fish of the dock Rv parking POOL SPA
The Caddyshack

The Caddyshack

Rotonda West FL
With a stay at this vacation home in Rotonda West (Oakland Hills), you'll be within a 10-minute drive of Lemon Bay and Oyster Creek Golf Club.
Opens in a new windowThe Caddyshack
Don't see what you're looking for?
See all available properties in Gasparilla Island
View all properties
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
1228 Holiday Homes
Lowest Price
AU$151
Highest Price
AU$443
Popular accommodation
Single family pool home in a quiet neighborhood, close to five beaches, , WATERFRONT LUXURY PRIVATE HEATED POOL&SPA/MIN TO BEACH/DOCK&LIFT/GULF ACCESS, Tiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time, Charming 2-bedroom beach themed Englewood house with heated pool and large yard., Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views, Waterfront Retreat: Fish, Kayak, and Paddle Board on Property + Pool + Hottub, Lakefront Exquisite Home in Placida Sands, A Fishing and Wildlife Phenomenon, Spacious 4-bedroom, harbor Acces ON canal, fish of the dock Rv parking POOL SPA, The Caddyshack

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$278 per night from 1 Apr to 2 Apr
AU$278
1 Apr - 2 Apr
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$342 per night from 6 Apr to 7 Apr
AU$342
6 Apr - 7 Apr
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
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$151 per night from 12 Apr to 13 Apr
AU$151
12 Apr - 13 Apr
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 ...
Opens in a new windowDays Inn by Wyndham Port Charlotte/Punta Gorda
Save an average of 15% on thousands of hotels when you're signed in
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
The price is AU$443 per night from 15 Apr to 16 Apr
AU$443
15 Apr - 16 Apr
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
Don't see what you're looking for?
See all available properties in Gasparilla Island
View all properties
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

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.