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

Gasparilla Island Vacation Rentals

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Our top choices for Gasparilla Island vacation rentals

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 CA $126
CA $426 total
includes taxes & fees
Aug 3 - Aug 4
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 CA $126
CA $426 total
includes taxes & fees
Aug 3 - Aug 4
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

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, (60 reviews)
The price is CA $126
CA $423 total
includes taxes & fees
Aug 1 - Aug 2
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

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 CA $126
CA $420 total
includes taxes & fees
Jul 30 - Jul 31
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches 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 CA $280
CA $565 total
includes taxes & fees
Aug 2 - Aug 3
MALU LANI Inn & Marina

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 CA $96
CA $742 total
includes taxes & fees
Aug 3 - Aug 4
Chadwick Cove Resort & Marina

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 CA $146
CA $495 total
includes taxes & fees
Aug 2 - Aug 3
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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, (27 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is CA $155
CA $506 total
includes taxes & fees
Aug 2 - Aug 3
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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 CA $159
CA $511 total
includes taxes & fees
Aug 1 - Aug 2
Waterview Vacation Retreat Close To Ocean

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 CA $142
CA $484 total
includes taxes & fees
Jul 30 - Jul 31
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

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 CA $178
CA $570 total
includes taxes & fees
Aug 4 - Aug 5
Casa Florida 🌴 waterfront home with boat ramp

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, (36 reviews)
"Very clean and served out brief visit well."
United States
Patricia M.
The price is CA $164
CA $511 total
includes taxes & fees
Jul 30 - Jul 31
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, 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 CA $212
CA $443 total
includes taxes & fees
Aug 1 - Aug 2
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 CA $254
CA $675 total
includes taxes & fees
Jul 30 - Jul 31
The Perfect Getaway with Private Beach Access

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 CA $95
CA $326 total
includes taxes & fees
Aug 27 - Aug 28
Charming 2-bedroom house in Englewood with WiFi and AC

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 CA $242
CA $523 total
includes taxes & fees
Aug 10 - Aug 11
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 CA $222
CA $605 total
includes taxes & fees
Aug 3 - Aug 4
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 CA $164
CA $553 total
includes taxes & fees
Aug 9 - Aug 10
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!
Grove City
10.0 out of 10, Exceptional, (10 reviews)
"Great stay, great host, and a great time!"
United States
Christopher G.
The price is CA $176
CA $444 total
includes taxes & fees
Jul 30 - Jul 31
2-bedroom pool house with golf cart in Englewood, close to the beaches!

Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (46 reviews)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is CA $238
CA $522 total
includes taxes & fees
Aug 13 - Aug 14
Turtle Cay at The Beach Shack! Come On Down!
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gasparilla Island vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gasparilla Island vacation rentals we have selected for you start as low as CA $277 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 vacation 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 vacation.

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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