Book Holiday Homes in Gasparilla Island

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Featured Holiday Homes in Gasparilla Island

Bohemian Sunrise

Bohemian Sunrise

Englewood
With a stay at this vacation home in Englewood, you'll be on the waterfront, just a 5-minute walk from Lemon Bay and 6 minutes by foot from Englewood Beach.
Bohemian Sunrise
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!
New Two story Cozy  House  Near Warm Mineral Springs

New Two story Cozy House Near Warm Mineral Springs

North Port
The price is AU$728 per night from 3 Jan to 4 Jan
AU$728
includes taxes & fees
3 Jan - 4 Jan 2025
With a stay at this vacation home in North Port, you'll be within a 5-minute drive of Warm Mineral Springs Pool and North Port Performing Arts Center.
New Two story Cozy House Near Warm Mineral Springs
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Punta Gorda Retreat Near Historic Downtown!

Punta Gorda Retreat Near Historic Downtown!

Punta Gorda
Located in Punta Gorda, this vacation home is within a 15-minute walk of First Macedonia Missionary Baptist Church and Bayfront Health Punta Gorda.
Punta Gorda Retreat Near Historic Downtown!
Adorable 1 Bedroom 1 Apartment

Adorable 1 Bedroom 1 Apartment

North Port
With a stay at this vacation home in North Port (Warm Mineral Springs), you'll be a 1-minute drive from Warm Mineral Springs Pool and 8 minutes from North Port ...
Adorable 1 Bedroom 1 Apartment
Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa.

Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa.

Englewood
Located in Englewood, this vacation home is by the sea, within a 5-minute drive of Lemon Bay and Manasota Beach.
Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa.
November,December and January Available!!!Special!!!!Your Dream Getaways Villa.

November,December and January Available!!!Special!!!!Your Dream Getaways Villa.

Rotonda West
With a stay at this vacation home in Rotonda West (Oakland Hills), you'll be within a 10-minute drive of Lemon Bay and Don Pedro Island State Park.
November,December and January Available!!!Special!!!!Your Dream Getaways Villa.
Private Pool, Rising Tide

Private Pool, Rising Tide

Port Charlotte
Located in Port Charlotte, this vacation home is in a rural location, a 3-minute drive from Ollie's Pond Park and 5 minutes from Peace River.
Private Pool, Rising Tide
Perfect Getaway with the pool

Perfect Getaway with the pool

North Port
The price is AU$678 per night from 30 Dec to 31 Dec
AU$678
includes taxes & fees
30 Dec - 31 Dec
When you stay at this vacation home in North Port, you'll be within a 10-minute drive of North Port Performing Arts Center and North Port Aquatic Center.
Perfect Getaway with the pool
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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
996 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$728
Popular accommodation
Bohemian Sunrise , Approximately 500 feet to beautiful Captiva Beach & private heated pool and spa!, New Two story Cozy House Near Warm Mineral Springs , Punta Gorda Retreat Near Historic Downtown!, Adorable 1 Bedroom 1 Apartment , Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa., November,December and January Available!!!Special!!!!Your Dream Getaways Villa., Private Pool, Rising Tide, Perfect Getaway with the pool

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$314 per night from 23 Dec to 24 Dec
AU$314
includes taxes & fees
23 Dec - 24 Dec
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$390 per night from 5 Jan to 6 Jan
AU$390
includes taxes & fees
5 Jan - 6 Jan 2025
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$190 per night from 29 Dec to 30 Dec
AU$190
includes taxes & fees
29 Dec - 30 Dec
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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Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

2.5 out of 5
9035 Mac Drive, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 29 Dec to 30 Dec
AU$197
includes taxes & fees
29 Dec - 30 Dec
A stay at Baymont by Wyndham Punta Gorda/Port Charlotte places you in the heart of Punta Gorda, within a 5-minute drive of Muscle Car City Museum and Charlotte ...
Baymont by Wyndham Punta Gorda/Port Charlotte
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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.