Book Holiday Homes in Gasparilla Island

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Featured Holiday Homes in Gasparilla Island

Tropical Retreat in Southwest Cape Coral

Tropical Retreat in Southwest Cape Coral

Cape Coral
With a stay at this vacation home in Cape Coral (Pelican), you'll be within a 10-minute drive of Palmetto-Pine Country Club and Rotary Park Environmental ...
Tropical Retreat in Southwest Cape Coral
Bohemian Sunrise

Bohemian Sunrise

Englewood
When you stay at this vacation home in Englewood, you'll be on the waterfront, within a 15-minute drive of Englewood Beach and Manasota Beach.
Bohemian Sunrise
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

North Port
With a stay at this vacation home in North Port, you'll be within a 10-minute drive of North Charlotte Regional Park and North Port Performing Arts Center.
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach
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Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes

Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes

Cape Coral
With a stay at this vacation home in Cape Coral (Pelican), you'll be within a 10-minute drive of Rotary Park Environmental Center and Veterans Foundation ...
Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes
Pool  Side  Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES

Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES

Cape Coral
With a stay at this vacation home in Cape Coral (Pelican), you'll be within a 15-minute drive of Edison Mall and Palmetto-Pine Country Club.
Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES
Luxury Canal Home-5 Bed, Boat rental, MIL Suite, bikes, pickleball,putting green

Luxury Canal Home-5 Bed, Boat rental, MIL Suite, bikes, pickleball,putting green

2 out of 5
Cape Coral
With a stay at this vacation home in Cape Coral (Pelican), you'll be within a 10-minute drive of Rotary Park Environmental Center and Veterans Foundation ...
Luxury Canal Home-5 Bed, Boat rental, MIL Suite, bikes, pickleball,putting green
Beautiful waterfront home with pool, game room, & dog-friendly

Beautiful waterfront home with pool, game room, & dog-friendly

Punta Gorda
With a stay at this vacation home in Punta Gorda (Punta Gorda Isles), you'll be within a 5-minute drive of Peace River and Hounds on Henry.
Beautiful waterfront home with pool, game room, & dog-friendly
Getaway Home with Hot Tub and Close to the Beach!

Getaway Home with Hot Tub and Close to the Beach!

Rotonda West
With a stay at this vacation home in Rotonda West (Oakland Hills), you'll be within a 10-minute drive of Don Pedro Island State Park and Little Gasparilla Island ...
Getaway Home with Hot Tub and Close to the Beach!
Approximately 500 feet to beautiful Captiva Beach & private heated pool and spa!

Approximately 500 feet to beautiful Captiva Beach & private heated pool and spa!

Captiva
With a stay at this vacation home in Captiva, you'll be by the sea, just a 2-minute walk from Captiva Beach and 5 minutes by foot from Jungle Drums.
Approximately 500 feet to beautiful Captiva Beach & private heated pool and spa!
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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
1066 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$588
Popular accommodation
Tropical Retreat in Southwest Cape Coral, Bohemian Sunrise , Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach, Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes, Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES, Luxury Canal Home-5 Bed, Boat rental, MIL Suite, bikes, pickleball,putting green, Beautiful waterfront home with pool, game room, & dog-friendly, Getaway Home with Hot Tub and Close to the Beach!, Approximately 500 feet to beautiful Captiva Beach & private heated pool and spa!

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$351 per night from 9 Mar to 10 Mar
AU$351
includes taxes & fees
9 Mar - 10 Mar
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$588 per night from 7 Mar to 8 Mar
AU$588
includes taxes & fees
7 Mar - 8 Mar
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
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$220 per night from 1 Apr to 2 Apr
AU$220
includes taxes & fees
1 Apr - 2 Apr
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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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$351 per night from 1 Apr to 2 Apr
AU$351
includes taxes & fees
1 Apr - 2 Apr
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 ...
The 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.

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^Subject to availability and chosen travel dates.