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Holiday rentals in Gasparilla Sound

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Top-rated holiday rentals in Gasparilla Sound

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

Guest favourite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Check our nearby sister property for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, check out our VIDEOS!
5–12 Dec, Individual Host
£515 per night
Guest favourite
Flat in Boca Grande
Historic Boca Grande: 2 Bedroom Flat:#6 Special Rt
We survived Ian and are ready to host you! A great 2 bedroom 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.
21–28 Oct
£234 per night
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 Jun, Individual Host
£623 per night

Popular amenities for Gasparilla Sound holiday rentals

Other great holiday rentals in Gasparilla Sound

Superhost
Cottage in Boca Grande
Charming beach cottage house with pool.
13–20 Jul, Individual Host
£384 per night
Guest favourite
Home in Placida
Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI
12–19 Jul, Professional Host
£568 per night
Guest favourite
Home in Englewood
"Lost Loon" Oceanfront Cottage by Roxy Rentals
30 Sept – 7 Oct, Professional Host
£415 per night
Guest favourite
Home in Placida
Little Gasparilla Island Beachfront Oasis
15–22 May
£534 per night
Guest favourite
Cottage in Englewood
Casa Tortuga- Beachfront Oasis
29 Jun – 6 Jul, Individual Host
£692 per night
Guest favourite
Cottage in Little Gasparilla Island
Happily Ever After
12–19 Apr, Individual Host
£317 per night
Guest favourite
Cottage in Englewood
Luxury Beach Resort Style Cottage
4–11 Aug, Professional Host
£399 per night
Guest favourite
Home in Captiva
My Sea Shack~ 1 minute to beach, SH Club, G-Cart
21–28 Aug
£299 per night
Guest favourite
Villa in Placida
Dolphin Watch
9–16 Aug, Professional Host
£773 per night
Guest favourite
Home in Placida
Family Tides on LGI - Golf Cart Included
20–27 Apr, Individual Host
£381 per night
Guest favourite
Home in Boca Grande
Perfect Beach House Excellent Location
7–14 Jan, Individual Host
£722 per night
Guest favourite
Home in Captiva
Private Island Luxury * Pool * Dock * Club Access
15–22 Jun, Professional Host
£837 per night

Destinations to explore