Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday rentals

Boca Grande Bliss: Stunning Condo with Boat Lift & Panoramas of Gulf Shores

Boca Grande Bliss: Stunning Condo with Boat Lift & Panoramas of Gulf Shores
Boca Grande
10.0 out of 10, Exceptional, (2 reviews)
"This property was fantastic is so many ways. The condo was completely renovated. The overall style is beautiful and functional. My family (2 adults and 3 boys) had a terrific experience. The views from the front and back of the property are both amazing! The property owners, Teresa and Kim were extremely helpful and attentive. Very much looking forward to returning to Boca North! "
United States
Ryan F.
Boca Grande Bliss: Stunning Condo with Boat Lift & Panoramas of Gulf Shores

The Beach Bus - Skoolie Camping!

The Beach Bus - Skoolie Camping!
Manasota
9.8 out of 10, Exceptional, (12 reviews)
"The schoolie was very comfortably situated as to be off the road and quite private. The hosts were very accommodating and provided the additional needs we requested. It was clean and fully stocked with plenty of bath and beach towels. The outdoor seating area is cute with lots of lush foliage. We enjoyed our stay immensely! "
United States
Michele
The price is NZ$460
includes taxes & fees
3 May - 4 May
The Beach Bus - Skoolie Camping!

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,146 reviews)
"Clean place Staff was friendly Place was fun "
United States
LaRae
The price is NZ$424
includes taxes & fees
26 Apr - 27 Apr
The Suites at Fishermen’s Village- 2 Bedroom Suites

Port Charlotte Waterfront Home

Port Charlotte Waterfront Home
2.5 star property
Port Charlotte
Port Charlotte Waterfront Home

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (285 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is NZ$394
includes taxes & fees
29 Apr - 30 Apr
Matlacha Tiny Village

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is NZ$701
includes taxes & fees
9 Apr - 10 Apr
MALU LANI Inn & Marina

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$792
includes taxes & fees
4 Apr - 5 Apr
Myakka River

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is NZ$1,161
includes taxes & fees
27 Apr - 28 Apr
Chadwick Cove Resort & Marina

Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location

Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location
Burnt Store Isles
10.0 out of 10, Exceptional, (22 reviews)
"House is always clean. Great location and very quiet neighborhood. "
United States
Yvonne T.
The price is NZ$650
includes taxes & fees
1 May - 2 May
Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location

Beach house

Beach house
Manasota Key
10.0 out of 10, Exceptional, (34 reviews)
"Great property. Great hosts. "
United States
Nick B.
The price is NZ$959
includes taxes & fees
18 Apr - 19 Apr
Beach house

Beautiful Entire House on a Canal W/ a Pool & Lanai - Serene & Private Setting!!

Beautiful Entire House on a Canal W/ a Pool & Lanai - Serene & Private Setting!!
New York Section
8.2 out of 10, Very good, (22 reviews)
"Loved the place! My kids loved the pool!"
United States
Leslie P.
The price is NZ$597
includes taxes & fees
7 Apr - 8 Apr
Beautiful Entire House on a Canal W/ a Pool & Lanai - Serene & Private Setting!!

Waterfront Home with Private Heated Pool, Dock, Wifi

Waterfront Home with Private Heated Pool, Dock, Wifi
Port Charlotte
9.6 out of 10, Exceptional, (82 reviews)
"This was a great stay, caught fish to eat... and pool was good, no steps to pool only a latter, so one family memeber was not able to use pool."
United States
Bradley L.
The price is NZ$1,072
includes taxes & fees
3 Apr - 4 Apr
Waterfront Home with Private Heated Pool, Dock, Wifi

The Bungalow - Captiva Beach Cottage on Turner Beach

The Bungalow - Captiva Beach Cottage on Turner Beach
Captiva
8.2 out of 10, Very good, (31 reviews)
"Beach was awesome!"
United States
juanita b.
The price is NZ$1,677
includes taxes & fees
3 Apr - 4 Apr
The Bungalow - Captiva Beach Cottage on Turner Beach

Gorgeous Marina Villas Residence at South Seas

Gorgeous Marina Villas Residence at South Seas
Captiva
9.0 out of 10, Wonderful, (10 reviews)
"Room was clean. Location was perfect. We’ll be booking again for sure next year "
United States
JOEL G.
The price is NZ$1,440
includes taxes & fees
23 Apr - 24 Apr
Gorgeous Marina Villas Residence at South Seas

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$484
includes taxes & fees
1 May - 2 May
Old Floridian cottage in Historic Gulf Village

Beachfront Palace with Birdseye Rooftop Deck!

Beachfront Palace with Birdseye Rooftop Deck!
Manasota Beach
9.8 out of 10, Exceptional, (15 reviews)
"Wonderful house!!!! We had such an amazing time. Highly highly recommend. Lots of stairs but bedrooms on main level helped with elderly family that said with us. "
United States
Raia R.
The price is NZ$1,696
includes taxes & fees
11 Apr - 12 Apr
Beachfront Palace with Birdseye Rooftop Deck!

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!
Manasota Key
9.2 out of 10, Wonderful, (53 reviews)
"Amazing weekend and the condo was perfect. Will definitely book again! "
United States
Irene P.
The price is NZ$857
includes taxes & fees
13 Apr - 14 Apr
Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!

Chic Captiva Villa Residence with Great Amenities

Chic Captiva Villa Residence with Great Amenities
Captiva
9.2 out of 10, Wonderful, (13 reviews)
"Host kept us informed of everything."
United States
Kirk C.
The price is NZ$1,186
includes taxes & fees
10 Apr - 11 Apr
Chic Captiva Villa Residence with Great Amenities

Beachfront 2BR North Captiva Cottage with Private Beach

Beachfront 2BR North Captiva Cottage with Private Beach
North Captiva
9.0 out of 10, Wonderful, (58 reviews)
"No complaints about the house. Location great, lodging great. Everything else overpriced. "
United States
Melinda G.
The price is NZ$2,513
includes taxes & fees
4 Apr - 5 Apr
Beachfront 2BR North Captiva Cottage with Private Beach

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds
South Venice
10.0 out of 10, Exceptional, (38 reviews)
"We were in town for a quick family reunion and stayed at the Poolside Oasis. We were delighted with the location (very close to restaurants, the beach, and of course the family) also the cleanliness of the property. We would definitely recommend this place and would stay here again. "
United States
Jeremiah P.
The price is NZ$769
includes taxes & fees
2 May - 3 May
Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gasparilla Island Hotel Reviews

Find out more about Gasparilla Island

Everything you need to know about Gasparilla Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gasparilla Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gasparilla Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gasparilla Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gasparilla Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gasparilla Island holiday rentals we have selected for you start as low as NZ$394 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gasparilla Island rentals

At Expedia, we put the best Gasparilla Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gasparilla Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gasparilla Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gasparilla Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.