Gasparilla Island holiday lettings

We found 158 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Gasparilla Island

Showing deals for:10 Oct - 17 Oct
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Gasparilla Island

  • Idyllic beach retreat: Gasparilla Island is perfect for families and couples seeking a relaxing coastal getaway.
  • Stunning scenery: Experience the island's breathtaking landscapes, including secluded beaches and picturesque surroundings.
  • Outdoor adventures: Enjoy a range of activities, from beachcombing to various outdoor excursions.
  • Charming accommodation: Choose from private holiday homes, stylish condos, and luxurious villas to suit your needs.
  • Welcoming locals: Immerse yourself in the friendly atmosphere and vibrant culture of Gasparilla Island.

Popular types of accommodation around Gasparilla Island

You’ve chosen Gasparilla Island for your getaway, and now it’s time to select the perfect accommodation. From charming houses and stylish condos to luxurious villas, the island offers a variety of options to suit every traveller's needs. Explore the best Gasparilla Island holiday rentals, including those on Little Gasparilla, and find the ideal vacation rental for a memorable stay.

  • Houses: The top choice for holidaymakers in Gasparilla Island, offering spacious living for families, couples, or groups of friends.
  • Condos: A popular selection for those seeking a blend of comfort and convenience, ideal for shorter stays.
  • Villas: These luxurious accommodations provide a serene retreat with ample amenities for a relaxing getaway.
  • Apartments: A practical option for independent travellers, perfect for enjoying a home-like atmosphere.
  • Cottages: Quaint and charming, these are ideal for those who prefer a cosy and intimate setting.**

Top attractions near Gasparilla Island

Gasparilla Island is an idyllic destination for beach and outdoor enthusiasts, offering stunning scenery and a wealth of cultural experiences. Visitors can indulge in beach adventures and explore the captivating landscapes of the island and its surrounding areas. Don't miss the Gasparilla getaway, where you can fully immerse yourself in this charming locale's natural beauty and vibrant atmosphere. It's the perfect spot for a memorable vacation, whether you're travelling solo or with loved ones.

  • Gasparilla Island State Park: This stunning national park offers a blend of adventure and natural beauty, featuring scenic trails, pristine beaches, and abundant wildlife, perfect for outdoor enthusiasts.
  • Boca Grande Beach: Renowned for its soft sands and tranquil waters, this beach is ideal for sunbathing and swimming, providing a quintessential Floridian beach vibe.
  • Whidden's Marina: A historic gem showcasing the local culture, this marina offers a glimpse into the island's maritime heritage, with opportunities for fishing and boat rentals.

Things to do recommended for couples

For a romantic getaway on Gasparilla Island, consider a round of golf at Oyster Creek Golf Club, only 7.5km away, or Burnt Store Golf & Activity Club, 8.1km away. Twin Isles Country Club, 10.6km from the island, offers a luxurious atmosphere perfect for couples.

Things to do recommended for families

Families visiting Gasparilla Island can enjoy a thrilling day at Sun Splash Water Park, relax at Cedar Point Environmental Park, or cheer on their favourite teams at Charlotte Sports Park, all offering unique experiences within a short drive from the island.

Things to do recommended for groups

Groups visiting Gasparilla Island can enjoy a vibrant shopping experience at Fishermen's Village, unwind at the scenic Riverwood Golf and Country Club, or immerse themselves in culture and entertainment at the Lemon Bay Playhouse, all within a short drive from the island.

Booking with Vrbo is a breeze

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay near Gasparilla Island

Gasparilla Island offers an idyllic beach retreat, perfect for families and couples seeking relaxation and adventure. With charming rentals on Little Gasparilla Island, visitors can enjoy the serene atmosphere, picturesque scenery, and friendly locals. From secluded beaches to outdoor excursions, this delightful getaway spot is ideal for those looking to unwind and explore the natural beauty of Florida’s coast.

  • Boca Grande: Situated a mere 124m from Gasparilla Island, Boca Grande is a charming city renowned for its stunning beaches and outdoor activities. Visitors flock here for the picturesque scenery and a laid-back atmosphere, making it an ideal spot for relaxation. The city boasts pristine beaches and a variety of recreational areas, along with delightful resorts and a shopping mall centre. Whether you're lounging on the beach or exploring local shops, Boca Grande offers a perfect blend of tranquillity and adventure.
  • Downtown Boca Grande Historic District: Located 186m from Gasparilla Island, the Downtown Boca Grande Historic District is a delightful neighbourhood known for its family-friendly environment and outdoor experiences. With lovely beaches and a vibrant shopping area, this district is a hub for those looking to enjoy a leisurely day out. Engage in underwater sports or enjoy a leisurely stroll through the historic streets, where charm meets modern amenities. The local attractions, including family beaches, make it a perfect destination for visitors of all ages.
  • Golden Beach: Golden Beach, positioned 435m away from Gasparilla Island, is a serene neighbourhood celebrated for its beautiful beaches and outdoor scenery. This area attracts travellers seeking relaxation and recreational activities, with access to shopping centres and a recreation centre. The allure of Golden Beach lies in its tranquil environment, where families can enjoy sun-soaked days by the shore. With its proximity to family-friendly beaches and the island, it's a splendid choice for a peaceful getaway.

Best time to go to Gasparilla Island

If you're planning a trip to Gasparilla Island, Boca Grande, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January and March to April, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January63.7°F (17.6°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February66.0°F (18.9°C)No Rain (Dry)SunnyAverageAverage
March68.7°F (20.4°C)No Rain (Dry)SunnySlightly HighSlightly High
April73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
August83.7°F (28.7°C)Light RainMostly SunnySlightly LowAverage
September81.9°F (27.7°C)Light RainMostly SunnyAverageSlightly Low
October77.5°F (25.3°C)Light RainMostly SunnySlightly LowSlightly Low
November71.2°F (21.8°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
December67.3°F (19.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

What do I need to keep in mind when booking a vacation around Gasparilla Island

If you're travelling with a group, family, or pets, or if you're considering longer stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Gasparilla Island with a group: Think about how many bedrooms you require, as well as any additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Gasparilla Island with young kids: Embarking on a journey with young children can present its difficulties. It's essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Gasparilla Island: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Gasparilla Island: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new getaways, pick up from where you last stopped, or manage your travel arrangements. You can easily access the properties you've previously saved or booked, now categorised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Burnt Store Golf & Activity Club (13.5 mi / 21.7 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)
  • Oyster Creek Golf Club (12.4 mi / 20 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.

More Holiday Rentals ideas

People also search for