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

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood
10.0 out of 10, Exceptional, (50 reviews)
"Clean and comfortable. Had everything I needed. Location is great if you want to be away from the hustle and bustle but still want to be near the beach and rivers. Katja and Alex were attentive and pleasant hosts."
United States
Mindy A.
The price is AU$430
includes taxes & fees
31 July - 1 Aug
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

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, (69 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 AU$432
includes taxes & fees
1 Aug - 2 Aug
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

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 AU$430
includes taxes & fees
6 Aug - 7 Aug
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

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 AU$576
includes taxes & fees
29 July - 30 July
MALU LANI Inn & Marina

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, (59 reviews)
"Everything was great, welcoming to pets, clean, laundry, relaxing areas to sit and great response to any questions we had. "
United States
DJ H.
The price is AU$430
includes taxes & fees
6 Aug - 7 Aug
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

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, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is AU$349
includes taxes & fees
6 Aug - 7 Aug
Charming 2-bedroom house in Englewood with WiFi and AC

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Oakland Hills
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AU$495
includes taxes & fees
29 July - 30 July
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

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, (76 reviews)
"Nice stay in good location"
United States
John W.
The price is AU$500
includes taxes & fees
28 July - 29 July
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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 AU$762
includes taxes & fees
11 Aug - 12 Aug
Chadwick Cove Resort & Marina

Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (18 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is AU$516
includes taxes & fees
27 July - 28 July
Waterview Vacation Retreat Close To Ocean

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, (26 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AU$475
includes taxes & fees
28 July - 29 July
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
The price is AU$437
includes taxes & fees
6 Aug - 7 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

The Perfect Getaway with Private Beach Access

The Perfect Getaway with Private Beach Access
Cape Haze
9.8 out of 10, Exceptional, (20 reviews)
"Lovely and peaceful yet plenty of things to do in the area. Enjoyed our stay."
United States
sharon b.
The price is AU$672
includes taxes & fees
6 Aug - 7 Aug
The Perfect Getaway with Private Beach Access

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Oakland Hills
10.0 out of 10, Exceptional, (35 reviews)
"Very clean and served out brief visit well."
United States
Patricia M.
The price is AU$515
includes taxes & fees
31 July - 1 Aug
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"Nice place on canal, having everything you need . Enjoyed the stay. "
United States
John M.
The price is AU$565
includes taxes & fees
24 Aug - 25 Aug
Casa Florida 🌴 waterfront home with boat ramp

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (8 reviews)
"The home was absolutely perfect , clean, spacious, and very comfortable. Beautifully decorated , beds were cozy, and everything was exactly as described. The host was friendly and responsive, which made the stay stress-free. Great location and a perfect home base for our family trip.”"
United States
Kelly R.
The price is AU$598
includes taxes & fees
6 Aug - 7 Aug
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 AU$283
includes taxes & fees
29 July - 30 July
Matlacha Tiny Village

Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (15 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is AU$296
includes taxes & fees
25 July - 26 July
Beautiful house with lake view

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (50 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
The price is AU$554
includes taxes & fees
11 Aug - 12 Aug
NEW!! The “WATERSIDE” COTTAGE~With dockage

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (28 reviews)
"The property was very clean and conveniently located. "
United States
Chris F.
The price is AU$550
includes taxes & fees
9 Aug - 10 Aug
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A 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

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$298 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. 

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