Holiday Rentals in Gasparilla Island

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Holiday Rentals in Gasparilla Island

Our top choices for Gasparilla Island holiday rentals

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (985)
"Great stay and well managed. Also, very clean and comfortable rooms. "
The price is €142
includes taxes & fees
25 Sept - 26 Sept
The Suites at Fishermen’s Village- 2 Bedroom Suites

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (98)
"Everything was perfect."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (265)
"Very nice place with all necesary accommodations for a Pleasant stay. "
The price is €155
includes taxes & fees
25 Sept - 26 Sept
Matlacha Tiny Village

4-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (141)
"We enjoyed our stay! Pool was nice! Good location close to beaches and restaurants! "
4-Bedroom Pool Home Convenient To Beaches

South Seas Beach Villa 2418 Coastal Luxury

9.8 out of 10, Exceptional, (78)
"The location was great to sit and enjoy the view. Short walk to the beach. "
South Seas Beach Villa 2418 Coastal Luxury

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (42)
"We had a wonderful time!"
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

Beautiful waterfront home, heated pool, bbq, dock, close to beaches, restaurant

10.0 out of 10, Exceptional, (47)
"Was traveling with my mother who is on hospice and the host was the most understanding, accommodating, and always extremely promptly responsive. The best Vrbo experience so far."
Beautiful waterfront home, heated pool, bbq, dock, close to beaches, restaurant

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay

South Seas Bayside Villa 4222

10.0 out of 10, Exceptional, (2)
"It was a wonderful getaway before school starts!"
South Seas Bayside Villa 4222

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is €447
includes taxes & fees
23 Sept - 24 Sept
Chadwick Cove Resort & Marina

The Barefoot Bungalow

9.4 out of 10, Exceptional, (119)
"Clean updated. Everything you would want in a beach place. Comfortable close to everything. Owner very responsiv3."
The Barefoot Bungalow

Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!

10.0 out of 10, Exceptional, (57)
"We had a family of 10 staying and it was a great property for all of us to enjoy time together with the pool, kayaks and games. It’s close to town and also private and quiet neighborhood. Great place!"
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!

“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

10.0 out of 10, Exceptional, (5)
"This property is amazing! Beautiful views and great fishing right off the dock. My wife and I stayed for our belated anniversary and we couldnt have been happier. We will be back."
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

9.2 out of 10, Wonderful, (19)
"We took our multigenerational family for a few days of quiet & sunshine. They loved the place so mush that they want to go back next year!We had a few problems with the house but the management team made it right.Lovely place to spend a few days - or more!"
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.0 out of 10, Wonderful, (62)
"This poolhouse was just perfect for us. It was well equipped for anything we could possibly need. The furnishings were very comfortable and the home was immaculate. The bonus was the grill and pool. We highly recommend this place to everyone. "
The price is €296
includes taxes & fees
19 Sept - 20 Sept
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

BEAUTIFUL OCEANFRONT BEACH LOCATION - FALL SPECIALS!!!!

9.8 out of 10, Exceptional, (69)
"Great trip!"
BEAUTIFUL OCEANFRONT BEACH LOCATION - FALL SPECIALS!!!!

Special:10% Discount! Book 2026 with private pool, elevator, ocean view!

10.0 out of 10, Exceptional, (15)
"The house and property are fantastic! The owners are very nice , easy to reach and helpful. Hoping to be back again soon! "
Special:10% Discount! Book 2026 with private pool, elevator, ocean view!

This Villa has it all! Waterfront - boat dock, tiki hut, hot tub, sauna & pool!

10.0 out of 10, Exceptional, (30)
"We had a great time with our kids and grandkids. Grandson loved fishing from the dock and kayaking with his dad. Great dining areas inside and out. We will definitely be returning. "
This Villa has it all! Waterfront - boat dock, tiki hut, hot tub, sauna & pool!

New luxury pool home, 2 min to beach, 360 water views, club available

9.8 out of 10, Exceptional, (108)
"We loved staying at Sublime! The owners and property managers were fantastic and attentive. Any obstacles were quickly resolved. Communication was great. My whole family (14 of us) had a great time. Core memories created left and right! Highly recommended!"
New luxury pool home, 2 min to beach, 360 water views, club available

Island Oasis on Manasota Key- Steps to both Gulf & Bay Access, Heated Pool

10.0 out of 10, Exceptional, (11)
"Nice and quiet place. Excellent property for a family vacation."
Island Oasis on Manasota Key- Steps to both Gulf & Bay Access, Heated Pool
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

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, apart-hotels, 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 €142 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.