Gasparilla Island Vacation Rentals

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Vacation Rentals in Gasparilla Island

Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (540)
"We stayed here while our kitchen was being painted. It was perfect for a little working staycation. The sunsets were beautiful from the balcony. "
The price is $159
$178 total
includes taxes & fees
May 22 - May 23
The Suites at Fishermen’s Village- 2 Bedroom Suites
Dock
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (229)
"We had a very nice stay at the tiny house! (Keep in mind, it is tiny) But very comfortable!! An unique experience and the property was outstanding compared to all the other units in the vicinity. It had a nice spacious canal front deck, and kayaks with a launching deck. Complete mini kitchen and great coffee preps. The beds were very comfortable and unit was very clean and updated. Decorated nicely! Loved the loft! Great alternative to a hotel room. We would definitely stay at Matlacha Tiny...
The price is $138
$229 total
includes taxes & fees
May 22 - May 23
Matlacha Tiny Village
Beach | On the beach
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
9.4 out of 10, Exceptional, (84)
"I love this cottage. Very clean and comfortable Thank you Angelo for everything!"
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
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Beach
Privacy in Paradise
10.0 out of 10, Exceptional, (58)
"Heat place to stay and anchor our adventures from. Thank you!"
Privacy in Paradise
Fridge, microwave, oven, coffee/tea maker
NEW LISTING! 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...
NEW LISTING! Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning
Pool | Outdoor pool, a heated pool
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
9.8 out of 10, Exceptional, (156)
"We absolutely loved everything about Villa Amara. Our hosts were incredibly kind and communicative and super helpful with all our questions. The villa is in a wonderful location in Cape Coral, and the house and the entire property is so well-kept, lovely, and homey. The view from the lanai and pool is stunning; we spent hours just sitting on the porch watching the water, trees, and birds. The house is beautifully appointed with everything guests could need for a comfortable stay. My husband and...
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
On the beach, sun loungers, beach towels
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
10.0 out of 10, Exceptional, (28)
"Our stay was fantastic from the first day to the last. John's home is welcoming and had everything we needed for our two week stay. The short walk to the beach was wonderful and you could hear the waves crashing the shoreline from the deck of the house. We will definitely be back!!"
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
Beach nearby, sun loungers, beach towels
Steps From Beach. Private entrance.
9.8 out of 10, Exceptional, (73)
"We had a great time, place was nice, so close to the beach, provided everything we needed for spending a weekend at the beach. We will definitely be back! Thanks so much for letting us stay at your place!"
Steps From Beach. Private entrance.
Fridge, microwave, oven, stovetop
🔆🏝LITTLE PARADISE🏝🔆
10.0 out of 10, Exceptional, (29)
"Nice place very comfortable. Enjoyed pool and golf cart."
🔆🏝LITTLE PARADISE🏝🔆
Beach nearby, sun loungers, beach towels
Sweet Home
7.6 out of 10, Good, (4)
"My parents were very satisfied with the property and the host. She was amazing and so helpful. The location was perfect for all their needs. They found everything they needed. Thank you very much. "
Sweet Home
Property grounds
Quiet Lemon Bay with Pool, Beach and Pier
9.8 out of 10, Exceptional, (23)
"We just bought a new home near Lemon Bay. It wasn’t ready so we had to look for reasonable accommodations for a week. We had some time to relax here because that’s what you do in Englewood. Very responsive host, clean, neat cottage among 9 others. The Sunsets were out of this world, the beach was 1 mile away. The people friendly and the pool refreshing. It’s not a 5 star resort BUT Better! No noisy crowds, fish off the long dock, read in the hammock! No one to bother you so make your own Pina...
Quiet Lemon Bay with Pool, Beach and Pier
Outdoor pool, a heated pool
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
9.8 out of 10, Exceptional, (36)
"We very much enjoyed our stay at your home! We hope to be back."
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
Pool
2-Bedroom Pool Home Convenient To Beaches
9.8 out of 10, Exceptional, (110)
"As a native Florida girl, this house felt like home. Great getaway spot!"
2-Bedroom Pool Home Convenient To Beaches
TV, fireplace
Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly
10.0 out of 10, Exceptional, (2)
"We loved the porch, the tranquility, and the location. We also appreciated the openness of the main living area."
Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly
Beach
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
10.0 out of 10, Exceptional, (30)
"The place was just as pictured and described! Quiet neighborhood and easy access. Only thing i might recommend is providing instructions for the thermostat as we struggled with programming it."
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
Terrace/patio
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
10.0 out of 10, Exceptional, (5)
"I was in town for work and this studio was in the absolute best location for me. 20 minutes from work and family and only few minutes to downtown Venice. The studio was in a perfect location. It's in a very quaint little neighborhood. It was very clean and the property taken care of. Laurie reached out a few times to make sure my stay was going well. She was very attentive to her guest. I will 100% be booking here agian for my trips."
The price is $79
$132 total
includes taxes & fees
Jun 14 - Jun 15
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
Fridge, microwave, oven, stovetop
Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways
9.8 out of 10, Exceptional, (20)
"New to VRBO. Loved this house, decor, pool, and hosts. Comfortable King bed, great pressure and hot water in the showers, pool and lanai made the difference. The first day was chilly but the heated pool allowed us to not miss a pool day. Highly recommend this house and hosts."
Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways
Exterior
Palm Island beach home with private pool. Island PARADISE awaits!!!
10.0 out of 10, Exceptional, (110)
"Perfect!"
Palm Island beach home with private pool. Island PARADISE awaits!!!
Outdoor dining
NEW! Waterfront Pool Home Canal Front in Quiet Area
9.2 out of 10, Wonderful, (10)
"Nice clean place that’d be great for a family. Pool was fantastic. Plenty of food options in a 10 minute or so radius. Would stay again."
The price is $75
$440 total
includes taxes & fees
Jun 16 - Jun 17
NEW! Waterfront Pool Home Canal Front in Quiet Area
Outdoor dining
Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.
9.2 out of 10, Wonderful, (43)
"Enjoyed our stay. Very nice hosts."
Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.
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See all available properties in Gasparilla Island
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.

Gasparilla Island Vacation Rental Travel Info

Popular accommodation
Gasparilla Island private vacation homes
International airports
Fort Myers, FL (RSW-Southwest Florida Intl.) and Punta Gorda, FL (PGD-Charlotte County)

Other types of properties in Gasparilla Island you may be interested in

Room, 1 King Bed | Down comforters, iron/ironing board, free WiFi, bed sheets
Boca Grande Hotel
2.5 star property
8.6 out of 10, Excellent, (467)
"The property itself is well kept and clean. The rooms are quiet. The staff is helpful. For the price and staying in a pristine area of old Florida, it really can’t be beat."
The price is $165
$184 total
includes taxes & fees
May 22 - May 23
Boca Grande Hotel
2 outdoor pools, open 8:00 AM to 8:30 PM, cabanas (surcharge)
Sunseeker Resort Charlotte Harbor
4.0 star property
9.4 out of 10, Exceptional, (214)
"If you're seeking the ultimate getaway, look no further than this resort oasis. Nestled amidst lush, meticulously manicured grounds, this hotel offers a serene escape from the hustle and bustle of everyday life. From the moment you arrive, you're greeted with unparalleled hospitality from a team that's not just helpful, but genuinely friendly. One of the standout features is the abundance of culinary options. With multiple dining venues on-site, you'll embark on a culinary journey that delights...
The price is $220
$280 total
includes taxes & fees
May 26 - May 27
Sunseeker Resort Charlotte Harbor
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (540)
"We stayed here while our kitchen was being painted. It was perfect for a little working staycation. The sunsets were beautiful from the balcony. "
The price is $159
$178 total
includes taxes & fees
May 22 - May 23
The Suites at Fishermen’s Village- 2 Bedroom Suites
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Gasparilla Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Recent reviews of Gasparilla Island properties
Expedia verified reviews

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

5/5 Excellent
"Wonderful and convenient property! Was upgraded to a newer and bigger room! Will stay here again!"
A verified traveler from Delaware stayed at Baymont by Wyndham Punta Gorda/Port Charlotte
Posted 14 hours ago
Baymont by Wyndham Punta Gorda/Port Charlotte