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, (698)
"Very enjoyable stay!"
The price is AU$651
includes taxes & fees
3 Jan - 4 Jan 2025
The Suites at Fishermen’s Village- 2 Bedroom Suites

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (238)
"Quiet area and great little houses. Rented the margarita and was not disappointed. At one point our door lock failed and the manager was there within a few minutes to fix it. Would stay again!"
The price is AU$389
includes taxes & fees
1 Jan - 2 Jan 2025
Matlacha Tiny Village

Privacy in Paradise

10.0 out of 10, Exceptional, (62)
"The property was more beautiful than we expected. There was more than enough space to lounge eat or relax. It was so clean we didn’t use the linens or pillows we brought with us. Anything we forgot to bring was in the pantry! And which host leaves us sodas, water and a bottle of great wine?… Richard! We didn’t want to leave and have decided to return in the spring, summer and fall next year. Thanks for treating us so well. Bravo Paradise!!"
Privacy in Paradise

Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning

8.0 out of 10, Very good, (2)
"While many homes in this neighborhood are still struggling to recover from hurricane Ian, this cozy litte place is primed for the tourist season! Recently updated with very pretty, Florida decor, and sitting right on the canal for easy access to the gulf, our time spent here was relaxing and pleasant indeed. One thing to note is, it may not be a good fit for an older person who is prone to falls. I care for my mom, and would not have wanted to bring her here, as most of the rooms are on...
Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning

Enjoy the view to the nature reserve from your private pool & spa at Villa Amara

9.8 out of 10, Exceptional, (162)
"Villa Amara is a comfortable, well equipped house located in an awesome spot on the canal. Private location, beautiful view across to protected land and awesome sunsets. The pool and hot tub are great and we used them everyday. "
Enjoy the view to the nature reserve from your private pool & spa at Villa Amara

BEAUTIFUL OCEANFRONT BEACH LOCATION - View dolphins & Manatees from Living Room!

9.8 out of 10, Exceptional, (68)
"The location is best on island from what I could tell. You can see gulf and bayside. Sunsets are amazing. Wildlife and seashells abound. The beaches are secluded for the most part with an occasion couple or family but night and day when compared to some of the more “touristy” places we have stayed along 30A. We will most certainly return. The owner and caretakers went out of their way to ensure our stay was amazing. Stephanie, Wendy and Bob were excellent communicators!"
BEAUTIFUL OCEANFRONT BEACH LOCATION - View dolphins & Manatees from Living Room!

Quiet Lemon Bay with Pool, Beach and Pier

9.6 out of 10, Exceptional, (33)
"It was a very comfortable home. Very clean and Quiet. The pool was clean and the fish were biting."
Quiet Lemon Bay with Pool, Beach and Pier

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (41)
"Fantastic property in Cape Coral. We unfortunately battled Tropical Storm Betty but still managed to squeeze in a lot of hot tub & pool time. Close to Fort Meyers Beach & Sanibel Island, our other favs. Would definitely come back! "
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

2-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (118)
"Great property, a real convenient location, and the owner is a real gentleman, the kind of person you'd want for a neighbor. He was very accommodating. "
2-Bedroom Pool Home Convenient To Beaches

The Turtle House-Miles and Miles of Private Beach-Sunset Views

9.6 out of 10, Exceptional, (23)
"We recently had the pleasure of staying at this beautiful beach vacation house, and it was an unforgettable experience! From the moment we arrived, we were greeted with breathtaking ocean views and the soothing sound of waves crashing on the shore. Location: 🌊🌴 The house is perfectly situated right on the beach, offering easy access to the sand and surf. We loved waking up to the sunrise over the ocean and enjoying our morning coffee on the spacious deck. Amenities: 🏠✨ The house itself...
The Turtle House-Miles and Miles of Private Beach-Sunset Views

Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly

9.4 out of 10, Exceptional, (3)
"Location is marvelous: Quiet, surrounded by nature. The porch alone is worth the stay, and having the beach a mere mile or so down the road? Eliminates questions about what to do (but bring footware!) Challenges: keycode system is insane, and also non-functional. Glad we had the keys instead. Especially as the promised beach towels were still in the cellar. Thanks to Vacasa team for working us through the entry issues. Otherwise? Spectacular location, very comfortable, and surrounded by all...
Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly

Charming & cozy studio, totally renovated in 2024.Close to beach.Pets welcome!

9.8 out of 10, Exceptional, (8)
"I was down looking at various properties ti purchase fir my wife and I. Laurie's place was right between the areas we were looking in, close to Venice and Englewood. The unit was clean, neat, stocked with necessities like coffee, tea and accessories. Ahe even bought a camping cot to accomodate a friend of mine from Michigan that has a place in Clearwater for a night. It is now available in the Goose's Shed for othwrs.Great stay and attentive hist.others. "
The price is AU$221
includes taxes & fees
4 Jan - 5 Jan 2025
Charming & cozy studio, totally renovated in 2024.Close to beach.Pets welcome!

Lovely apartment 5 minutes to the beach, restaurants, shopping and services

10.0 out of 10, Exceptional, (38)
"Owner had great communication with my concerns "
Lovely apartment 5 minutes to the beach, restaurants, shopping and services

Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways

10.0 out of 10, Exceptional, (26)
"WONDERFUL PROPERTY. VERY CLEAN AND IN A NICE NEIGHBORHOOD."
Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways

NEW! Waterfront Pool Home Canal Front in Quiet Area

9.4 out of 10, Exceptional, (11)
"House was clean and no issues with checking in. Pool was beautiful. Beds weren’t very comfortable would recommend getting newer updated beds. Needed more linens like more towels, extra bedding when it’s colder. Otherwise great stay would recommend others to stay at this house."
NEW! Waterfront Pool Home Canal Front in Quiet Area

Cape Coral Dream Lake Villa - Heated Pool & Spa

9.6 out of 10, Exceptional, (19)
"We really enjoyed the house and location. No complaints at all and we fully recommend renting this house!"
Cape Coral Dream Lake Villa - Heated Pool & Spa

Perfect getaway! Newly remodeled waterfront suite.

8.6 out of 10, Excellent, (22)
"This place was absolutely perfect for my mother and I. The location was easily accessed. The hosts are so kind and as a bonus, they have a sweet little cat who loves to welcome their guests. I'd 100% recommend and would stay again."
Perfect getaway! Newly remodeled waterfront suite.

Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

9.2 out of 10, Wonderful, (44)
"Enjoyed our stay. Very nice hosts."
Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

Sought after SW Cape Coral in beautiful waterfront neighborhood

9.6 out of 10, Exceptional, (43)
"Great communication with the host. Comfortable house and neighborhood. Excellent pool. Nice fenced in yard. And don’t worry when you reserve it and they send a message that says you aren’t allowed to turn the AC below 73 degrees. We like it cool and it was perfectly cool in the house!"
Sought after SW Cape Coral in beautiful waterfront neighborhood

Pool & Fire Pit: Cape Coral Golf Course Getaway

10.0 out of 10, Exceptional, (4)
"House is perfect nice neighborhood the host is super nice and the communication on point no issues answer any questions within minutes I have no words to describe the amazing time I had with my family thanks Julie"
Pool & Fire Pit: Cape Coral Golf Course Getaway
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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Other types of properties in Gasparilla Island you may be interested in

Boca Grande Hotel

2.5 star property
8.6 out of 10, Excellent, (505)
"The resort was unfortunately damaged by the storm. most restaurants and the pool Was Closed. The stay was nice , quiet clean and the A/c worked great. Im sure when its all back in order it will be fantastic . I will be returning "
The price is AU$333
includes taxes & fees
5 Jan - 6 Jan 2025
Boca Grande Hotel

Sunseeker Resort Charlotte Harbor

4.5 star property
9.2 out of 10, Wonderful, (670)
"Great resort and easy access to all things in the area "
The price is AU$393
includes taxes & fees
4 Jan - 5 Jan 2025
Sunseeker Resort Charlotte Harbor

Days Inn by Wyndham Port Charlotte/Punta Gorda

3.0 star property
7.8 out of 10, Good, (1005)
"Great staff clean room nice breakfast room"
The price is AU$209
includes taxes & fees
29 Dec - 30 Dec
Days Inn by Wyndham Port Charlotte/Punta Gorda
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.