A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday rentals

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is NZ$244
includes taxes & fees
2 July - 3 July
Charming cottage for 2 across warm mineral springs park

4 Mi to Hospitals! Port Charlotte Home w/ Lanai

4 Mi to Hospitals! Port Charlotte Home w/ Lanai
3.0 star property
Port Charlotte
The price is NZ$563
includes taxes & fees
2 July - 3 July
4 Mi to Hospitals! Port Charlotte Home w/ Lanai

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is NZ$954
includes taxes & fees
8 July - 9 July
Chadwick Cove Resort & Marina

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, (1,248 reviews)
"Great location clean and specious"
United States
Kathryn
The price is NZ$346
includes taxes & fees
30 July - 31 July
The Suites at Fishermen’s Village- 2 Bedroom Suites

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
9.8 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay at this property. Home is perfect for couples or a small family. Very clean and adorable set up. Love the back yard and lanai! Thanks for a great stay - we would stay again."
United States
Mandy A.
The price is NZ$424
includes taxes & fees
7 July - 8 July
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (292 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
The price is NZ$348
includes taxes & fees
8 July - 9 July
Matlacha Tiny Village

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (74 reviews)
"Very nice property, close to beaches and shopping. I especially liked that they had pretty much everything you needed for a beach day."
United States
Melissa
The price is NZ$568
includes taxes & fees
2 July - 3 July
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (54 reviews)
"Apartment was very clean! Lots of outdoor seating options. Nice beach chairs to take to the beach."
United States
Apryl H.
The price is NZ$526
includes taxes & fees
5 July - 6 July
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.4 out of 10, Exceptional, (3 reviews)
"The house was very clean and well accommodating. There was room for our boat in the driveway. Will definitely stay again if in the area."
United States
Jeremy
The price is NZ$503
includes taxes & fees
7 July - 8 July
Path to Paradise.

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (58 reviews)
"Very good communication from hosts, property was very clean and great location 10/10"
United States
Ashley R.
The price is NZ$526
includes taxes & fees
5 July - 6 July
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (66 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is NZ$421
includes taxes & fees
8 July - 9 July
Completely remodeled beautiful waterfront property on canal with dock

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (68 reviews)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is NZ$527
includes taxes & fees
13 July - 14 July
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (3 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is NZ$424
includes taxes & fees
12 July - 13 July
Charming 2-bedroom house in Englewood with WiFi and AC

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is NZ$688
includes taxes & fees
6 July - 7 July
MALU LANI Inn & Marina

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean and conveniently located. "
United States
Chris F.
The price is NZ$663
includes taxes & fees
2 July - 3 July
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is NZ$859
includes taxes & fees
7 July - 8 July
Home < 1-mi Walk to Warm Mineral Springs Park!

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
South Venice
9.8 out of 10, Exceptional, (56 reviews)
"The backyard was large and well kept , the grandchildren loved being able to use the swing and above ground pool."
United States
gale o.
The price is NZ$720
includes taxes & fees
2 July - 3 July
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

Sunshine Hideaway 6 mins to Warm Mineral Springs

Sunshine Hideaway 6 mins to Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful home. Hoping to book future travels here again"
United States
Jacqueline
The price is NZ$456
includes taxes & fees
8 July - 9 July
Sunshine Hideaway 6 mins to Warm Mineral Springs

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"Very clean property. Great outdoor space. Very quiet and relaxing area. Would definitely stay again. "
United States
Tom D.
The price is NZ$769
includes taxes & fees
2 July - 3 July
Myakka River

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (24 reviews)
"Ammenities were great.Everything you need.Bring a carry on and check inWill stay again."
United States
Keenan F.
The price is NZ$561
includes taxes & fees
2 July - 3 July
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
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$346 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. 

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