Gasparilla Island holiday lettings

We found 146 holiday rentals — enter your dates for availability

Find spaces that suit your style

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  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Delight in the waterfront landscape of Gasparilla Island

Enjoy the monuments and other features of Gasparilla Island. This walkable and welcoming city is well known for its island views, golfing and parks. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Gasparilla Island

Are you looking for things to do during your stay? Venture out of your holiday home and experience everything that Gasparilla Island has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Cape Haze Pioneer Trail Park (12.6 mi / 20.3 km)
  • Coral Oaks Golf Course (15 mi / 24.2 km)
  • Riverwood Golf and Country Club (16.4 mi / 26.4 km)
  • Royal Tee Golf Club (16.7 mi / 26.9 km)
  • Tails and Scales Charters (5.4 mi / 8.7 km)
  • Calusa Heritage Trail (9.2 mi / 14.8 km)

Exploring the natural features in Gasparilla Island

Whether you're looking for fun outdoor activities or just want to take in the scenery, Gasparilla Island is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Gasparilla Island State Park (1.3 mi / 2 km)
  • Boca Grande Beaches (2 mi / 3.2 km)
  • Boca Grande Beach (4.1 mi / 6.6 km)
  • Little Gasparilla Island Beach (5.4 mi / 8.6 km)
  • Useppa Island (6.9 mi / 11.1 km)
  • Cabbage Key (7.1 mi / 11.4 km)

Frequently asked questions

What is the most popular type of holiday rental accommodation in Gasparilla Island?
Based on our data, houses are the most in-demand holiday rental type in Gasparilla Island. But of course, everyone’s idea of an epic stay isn’t going to be the same. Vrbo has holiday homes with every size, shape and budget in mind, and we’ll help you find the perfect match.
How much does it cost to rent a holiday rental in Gasparilla Island?
Season, property type and length of stay are among the factors that can affect the price of a holiday home. Simply add your travel dates to find your dream escape. From cosy country cottages to plush villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Gasparilla Island?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Type in your Gasparilla Island travel dates to view your options on Vrbo. Did someone just say “hot tub”? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday rentals in Gasparilla Island?
There certainly are. You’ll have a choice of 78 stays that welcome pets in Gasparilla Island on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your puppy can be near his favourite humans.
Can I rent a house with a pool in Gasparilla Island?
Grab your swimming gear and swim ring, because there are 46 houses with a private pool in Gasparilla Island. Base yourself at one of these superb holiday homes and make every day a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Gasparilla Island?
An ocean view, a barbecue grill and a nearby river head the list of most popular rental amenities in Gasparilla Island. Whether you plan to go solo, with your spouse or a group of family members, Vrbo can help you find a holiday home that fits your tastes with all the features you’re looking for.
Are there large group holiday rentals in Gasparilla Island?
Gasparilla Island has five holiday rentals that can fit 10 or more guests. These properties come with the space and privacy you need to enjoy good times with friends and family.
Are there holiday rentals in Gasparilla Island that welcome kids?
Gasparilla Island has 77 family-friendly holiday homes. And finding a stay that welcomes little ones is a cinch with Vrbo’s “Properties good for families” filter. On top of having the entire place to yourselves, you can also look forward to perks and amenities such as extra bedrooms, full kitchens and private pools.
What are the top attractions for families in Gasparilla Island?
You’ll find lots of awesome things to see and do with the family in Gasparilla Island, including:

  • Boca Grande Beaches
  • Gasparilla Island State Park
  • Uncle Henrys Marina

Are there one-bedroom holiday rentals in Gasparilla Island?
Take your pick from 13 one-bedroom rentals in Gasparilla Island. Whether you’d prefer a comfy cottage or a condo, our one-bedroom rentals are perfect if you don’t need a lot of space. One of the main perks of having your own digs? You won’t need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Gasparilla Island?
Take your pick of 24 two-bedroom properties in Gasparilla Island. Put the kids in the second room or maybe fill it with a couple of your best buddies. There’s a comfy spot for whoever’s fortunate enough to come along for the ride.
Are there holiday rentals with WiFi in Gasparilla Island?
Pick from 33 holiday rentals with WiFi in Gasparilla Island. If you’d like to disconnect from the world on your holiday, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Gasparilla Island?
Pick your travel dates and then make use of our filters to locate holiday rentals with air conditioning in Gasparilla Island on Vrbo. With 77 air-conditioned properties available here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday rental in Gasparilla Island?
The minimum age is normally 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your chosen Gasparilla Island stay before booking your escape.
How long can I rent a holiday rental in Gasparilla Island for?
The amount of time you can rent a Gasparilla Island holiday rental for varies depending on the property. Simply tap in your dates of travel to see available options that offer long-term stays. They include everything you need to make your extended getaway more convenient and comfortable, such as kitchens and backyards. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can have a longer stay for less.

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