Gasparilla Island vacation rentals

We found 107 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024

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    Enjoy full kitchens, laundry, pools, yards and more
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Delight in the waterfront landscape of Gasparilla Island

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

Sightseeing in and around Gasparilla Island

Are you looking for attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Gasparilla Island a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Riverwood Golf and Country Club (16.4 mi / 26.4 km)
  • Cape Haze Pioneer Trail Park (12.6 mi / 20.3 km)
  • Coral Oaks Golf Course (15 mi / 24.2 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 adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Gasparilla Island. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)