Gasparilla Island Holiday Rentals

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Holiday Rentals in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (994)
"Clean room great staff "
The price is NZ$371
includes taxes & fees
3 Oct - 4 Oct
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 NZ$353
includes taxes & fees
5 Oct - 6 Oct
Matlacha Tiny Village

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

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

10.0 out of 10, Exceptional, (50)
"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

South Seas Marina Villa 704 - Gulf & Marina Views

9.4 out of 10, Exceptional, (15)
"The condo was very clean and comfortable for our family. It was 2 adults and 2 teenagers and we had plenty of room. The location was quiet. We would stay here again."
South Seas Marina Villa 704 - Gulf & Marina Views

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

10.0 out of 10, Exceptional, (57)
"We had a wonderful time. The pool was great. We will definitely be back soon."
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!

4-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (143)
"This is our second time at this vacation home and we absolutely love everything about it! From the location, the pool, the house, and the area itself is so quiet as well as peaceful. Not far from beaches. Also, that it is pet friendly which is a plus! Highly recommend this place. "
4-Bedroom Pool Home Convenient To Beaches

HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

10.0 out of 10, Exceptional, (209)
"Was a perfect stay. Would recommend it to everyone"
HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

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

10.0 out of 10, Exceptional, (12)
"Nice and quiet place. Excellent property for a family vacation."
Island Oasis on Manasota Key- Steps to both Gulf & Bay Access, Heated Pool

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

10.0 out of 10, Exceptional, (5)
"We had been looking forward to our family vacation for quite awhile with excitement and the home did not disappoint! Clean, light and bright with a stunning view. We will definitely be back!"
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

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!

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

Big on the Beach House, Oceanfront with Stunning views!

9.8 out of 10, Exceptional, (70)
"Great trip!"
Big on the Beach House, Oceanfront with Stunning views!

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is NZ$911
includes taxes & fees
7 Oct - 8 Oct
Chadwick Cove Resort & Marina

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.6 out of 10, Excellent, (17)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

South Seas Beach Villa 2418 Coastal Luxury

9.8 out of 10, Exceptional, (79)
"Great location! Centrally located and easy to get to beach and pool. Beautiful interior"
South Seas Beach Villa 2418 Coastal Luxury

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!

Windows on the Water "W.O.W" An ocean front oasis!

10.0 out of 10, Exceptional, (60)
"Great place enjoy the views"
Windows on the Water "W.O.W" An ocean front oasis!

1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option

10.0 out of 10, Exceptional, (116)
"Recently remodeled (basically new) house was perfect for our group. Very nice inside and out. All furniture was excellent. We had 11 adults, 2 kids and 1 toddler. Plenty of room for all. large kitchen and dining area made it easy to cook breakfast and dinners for the entire group. 2 complete refrigerators was an excellent idea and really made it nice to store food plus there were two icemakers for drinks! Shally's was fantastic for check-in and check-out. Communication was great with...
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
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, 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$353 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.