Holiday rentals in Gasparilla Island

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Top-rated holiday rentals in Gasparilla Island

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Flat in Boca Grande

4.89 out of 5 average rating, 178 reviews

Downtown Boca Grande Efficiency Flat#3-Special Rt

We survived Ian and are ready to host you! A great efficiency, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Located across the street from The Temp Restaurant, down the block from Hudson's Market and around the corner from Sister's Pizza. Going to the beach, no worries, it is just down the road. Rent our place through Air BnB and receive a 10% discount on golf cart and bike rentals. You’ll love my place because of the location, and the neighborhood.

8–15 Aug

€ 189 per night
Superhost

Guest house in Englewood

4.93 out of 5 average rating, 232 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

31 Jul – 7 Aug

€ 355 per night
Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 53 reviews

Private Cottage on Manasota Key

If you are looking for a Vacation Cottage with Old Florida Charm and a Private Beach, look no further. The view from the cottage is so amazing, it was the filming site for a movie starring Woody Harrelson, but hey, this is about you. Unwind in our 2 bedroom, 1 bath cottage with all of the amenities of home. Washer, dryer, full kitchen, outdoor shower, the beach, and panoramic views of the Gulf of Mexico. Pelican Shores Cottages are absolutely delightful, you and your family are sure to enjoy.

11–18 Nov

€ 622 per night

Popular amenities for Gasparilla Island holiday rentals

Other great holiday rentals in Gasparilla Island

Guest favourite

Home in Placida

5.0 out of 5 average rating, 54 reviews

Little Gasparilla Island Beachfront Oasis

20–27 Jan

€ 625 per night
Guest favourite

Guest suite in Englewood

4.95 out of 5 average rating, 66 reviews

Cozy Studio with Balcony & View of Gulf!

26 Aug – 2 Sep

€ 139 per night
Guest favourite

Flat in Englewood

4.98 out of 5 average rating, 82 reviews

Super cute fun studio steps from everything beachy

5–12 Sep

€ 163 per night
Guest favourite

Flat in Englewood

5.0 out of 5 average rating, 12 reviews

1st Floor Pvt Beach Access, New! - Heron's Walk #2

3–10 Nov

€ 135 per night
Guest favourite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

23–30 Sep

€ 516 per night
Guest favourite

Cottage in Englewood

4.88 out of 5 average rating, 91 reviews

Free kayak/bikes/walk to beach/full cottage #1

24 Sep – 1 Oct

€ 147 per night
Guest favourite

Home in Englewood

4.97 out of 5 average rating, 32 reviews

Unique-Cotton Cottage

29 Oct – 5 Nov

€ 141 per night
Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 43 reviews

Casa Tortuga - Beachfront Oasis

26 Nov – 3 Dec

€ 810 per night
Superhost

Villa in Placida

4.91 out of 5 average rating, 11 reviews

Dolphin Watch

30 Nov – 7 Dec

€ 1,033 per night
Guest favourite

Cottage in Placida

4.97 out of 5 average rating, 37 reviews

Simply Adrift Island Cottage

7–14 Jul

€ 364 per night
Guest favourite

Home in Rotonda West

5.0 out of 5 average rating, 15 reviews

Paradise Found!

3–10 Nov

€ 157 per night
Guest favourite

Apartment in Cape Haze

4.83 out of 5 average rating, 12 reviews

Comfortable 1 bedroom Condo w/ Marina and ICW view

21–28 Jun

€ 136 per night

Destinations to explore