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, (1002)
"Fantastic place to stay! Everything was top notch! "
The price is AU$317
includes taxes & fees
16 Oct - 17 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, (99)
"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 AU$314
includes taxes & fees
22 Oct - 23 Oct
Matlacha Tiny Village
Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is AU$814
includes taxes & fees
19 Oct - 20 Oct
Chadwick Cove Resort & Marina
Paradise Cove at Lemon Bay
3.5 star property
8.2 out of 10, Very good, (79)
"Nice, quiet area. Private and had everything we needed! Very nice staff!! "
Paradise Cove at Lemon Bay
120 steps to beach! Safely on the beach side of the road!
9.8 out of 10, Exceptional, (186)
"We wanted a local getaway and this home has an excellent location, was clean, and the owners were lovely. Highly recommend to any Floridians wanting to "escape" to the beach for a few days! "
The price is AU$924
includes taxes & fees
31 Oct - 1 Nov
120 steps to beach! Safely on the beach side of the road!
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
10.0 out of 10, Exceptional, (57)
"Very nice, and clean home, with a pool the kids loved; but fishing in the backyard too"
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
Big on the Beach House, Oceanfront with Stunning views!
9.8 out of 10, Exceptional, (71)
"Great trip!"
Big on the Beach House, Oceanfront with Stunning views!
“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
Beautiful waterfront home, heated pool, bbq, dock, close to beaches, restaurant
10.0 out of 10, Exceptional, (51)
"We had just a short stay but the house was gorgeous. The host was super helpful and quick to answer with any questions or concerns we had. We would definitely stay again!"
Beautiful waterfront home, heated pool, bbq, dock, close to beaches, restaurant
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
9.2 out of 10, Wonderful, (19)
"Wonderful stay with a large family of 16. Dreamcatcher is a beautifully decorated home that had everything we needed! From the gorgeous views, comfortable beds, nice showers, and fully stocked kitchen it is truly a slice of paradise! There were two golf carts to explore the island but also a short walk to the beach where we watched the most beautiful sunsets. Would highly recommend and hope to stay at Dreamcatcher again! "
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
South Seas Marina Villa 704 - Gulf & Marina Views
9.4 out of 10, Exceptional, (15)
"We’ve had so "
South Seas Marina Villa 704 - Gulf & Marina Views
Sandcastle Captiva luxurious, 2 minutes from beach, private pool, bay views
8.4 out of 10, Very good, (9)
"We had a wonderful week at Sandcastle! We were able to walk to the beach in around 5-10 minutes but I would suggest a golf cart or car to get any chairs, coolers, umbrellas, etc to the beach. It’s a bit far to carry a lot of stuff."
Sandcastle Captiva luxurious, 2 minutes from beach, private pool, bay views
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
HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
10.0 out of 10, Exceptional, (210)
"This was our second trip and just like the first time it was wonderful. Other than maybe to go get groceries or out to dinner a time or two this location has everything we needed to just stay in and enjoy a nice week away."
HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
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!
4-Bedroom Pool Home Convenient To Beaches
9.8 out of 10, Exceptional, (145)
"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
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
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
Coastal duplex with private beach access & deck - dog-friendly
8.0 out of 10, Very good, (10)
"Overall we had a nice, enjoyable stay. The place was clean. "
The price is AU$576
includes taxes & fees
19 Oct - 20 Oct
Coastal duplex with private beach access & deck - dog-friendly
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 favourite 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 depend 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 AU$314 per night. Entering your travel dates in the search wizard might find you 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.