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
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.
12–19 SeptIndividual Host,
£163 per night
4.9 out of 5 average rating, 172 reviews
Guest favourite
Home in Captiva
The Pearl Beach House, North Captiva Island,FL
This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs
8–15 JulIndividual Host,
£625 per night
4.98 out of 5 average rating, 104 reviews
Guest favourite
Apartment in Englewood
Gulf Side Condo Englewood Florida
A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.
2–9 MayIndividual Host,
£225 per night
4.94 out of 5 average rating, 116 reviews

Popular amenities for Gasparilla Island holiday rentals

Other great holiday rentals in Gasparilla Island

Superhost
Cottage in Boca Grande
Charming beach cottage house with pool.
11–18 JulIndividual Host,
£385 per night
4.87 out of 5 average rating, 83 reviews
Guest favourite
Cottage in Englewood
Private Cottage on Manasota Key
15–22 OctIndividual Host,
£500 per night
5.0 out of 5 average rating, 53 reviews
Guest favourite
Home in Placida
Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI
10–17 AugProfessional Host,
£570 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Boca Grande
Cavana Boca-Yacht Watch Sleeps 8
27 Aug – 3 SeptIndividual Host,
£716 per night
4.89 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Englewood
Casa Tortuga- Beachfront Oasis
28 Nov – 5 DecIndividual Host,
£694 per night
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Englewood
"Lost Loon" Oceanfront Cottage by Roxy Rentals
9–16 FebProfessional Host,
£643 per night
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Placida
Little Gasparilla Island Beachfront Oasis
6–13 DecIndividual Host,
£535 per night
5.0 out of 5 average rating, 53 reviews
Guest favourite
Home in Englewood
Vacation Condo- Beach Access!
28 Jul – 4 AugIndividual Host,
£364 per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Villa in Placida
Dolphin Watch
9–16 AugProfessional Host,
£775 per night
4.91 out of 5 average rating, 11 reviews
Guest favourite
Home in Boca Grande
Perfect Beach House Excellent Location
7–14 JanIndividual Host,
£723 per night
4.95 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Little Gasparilla Island
Happily Ever After
31 Dec – 7 JanIndividual Host,
£318 per night
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Placida
Family Tides on LGI - Golf Cart Included
30 May – 6 JunIndividual Host,
£398 per night
5.0 out of 5 average rating, 12 reviews

Destinations to explore