Gasparilla Island Holiday Rentals

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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 AU$254
includes taxes & fees
28 Sept - 29 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 AU$276
includes taxes & fees
25 Sept - 26 Sept
Matlacha Tiny Village

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

7.8 out of 10, Good, (21)
"Great spit in Venice to bring the dogs and enjoy some early summer vacations "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

4-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (140)
"Nice place very quiet location. Pool was great (Heated)Took about 5-8 min to get to the beach.Would stay again. Nick was an excellent host"
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, (1)
"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 AU$878
includes taxes & fees
29 Sept - 30 Sept
Chadwick Cove Resort & Marina

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (119)
"Clean & comfortable with the beach just steps away!"
Sand in Your Toes . . . Right Out Your Front Door!

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.8 out of 10, Excellent, (16)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

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)
"Loved our stay! "
The price is AU$518
includes taxes & fees
17 Oct - 18 Oct
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!

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
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 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$254 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.