Photo by Tom Hunt

Little Gasparilla Island Holiday Rentals

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Holiday Rentals in Little Gasparilla Island

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!!
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!
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (550)
"Fully equipped condo set up. Very clean and comfortable. Employees were very helpful. If they could screen in the balconies it would be great as bugs and birds make it uncomfortable."
The price is NZ$290
per night
10 Jun - 11 Jun
The Suites at Fishermen’s Village- 2 Bedroom Suites
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Exterior
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (113)
"All updated! Comfortable and clean. "
The price is NZ$243
per night
2 Jun - 3 Jun
Kon Tiki Inn
Dock
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (230)
"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 NZ$374
per night
28 May - 29 May
Matlacha Tiny Village
Pool
Beautiful and comfortable home with a pool - 8 minutes to Gulf beaches!!!
10.0 out of 10, Exceptional, (1)
"We were so please with this home! The pool and pool area was amazing, with great privacy and tropical foliage all around. Communication with the homeowner was very easy. The home had everything we needed for our month long stay. The beds were comfortable, as was the living area. The location was perfect, central to the beaches and activities of Venice & Englewood. We would deffinetley stay there again if visiting Venice!"
Beautiful and comfortable home with a pool - 8 minutes to Gulf beaches!!!
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.
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
Pool
2-Bedroom Pool Home Convenient To Beaches
9.8 out of 10, Exceptional, (111)
"Extremely clean!!! The pool area is private with a wooded area directly behind the house. Highly recommend!!!"
2-Bedroom Pool Home Convenient To Beaches
Beach
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
10.0 out of 10, Exceptional, (31)
"This rental was very dreamy. It was clean, affordable, easy to talk to the landlord, and had many ammenities. They had some beach equiptment for when we went to the beach as well as beach towels. The neighborhood was great and we felt like we could come and go as needed. We would absolutely stay here again. Thank you!"
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 NZ$215
per night
14 Jun - 15 Jun
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
Exterior
Palm Island beach home with private pool. Island PARADISE awaits!!!
10.0 out of 10, Exceptional, (111)
"What a wonderful weekend we had at this cute home! We loved hanging in the pool area there after a long day on the beach. Warren was quick to respond to messages. Only wish we could have stayed a little longer!!"
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 NZ$719
per night
15 Jun - 16 Jun
NEW! Waterfront Pool Home Canal Front in Quiet Area
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
Property grounds
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.
Property grounds
New Listing! Englewood Retreat!
10.0 out of 10, Exceptional, (3)
"Plenty of room. Comfortable. Well appointed. Away from the hustle and bustle, but still close enough to find plenty to do. The exercise pool/hot tub was a plus for sure. We would definitely stay here again."
The price is NZ$877
per night
10 Jun - 11 Jun
New Listing! Englewood Retreat!
On the beach, sun-loungers, beach towels
60 STEPS TO BEST BEACH ON THE KEY! PRIVATE HOME ⭐⭐⭐⭐⭐ BEAUTIFUL BOTANICAL GARDEN
9.8 out of 10, Exceptional, (103)
"Perfect place for what my husband and I needed. Pool table was fun, shed full of beach toys. We didn't need to use our vehicle our entire stay - rode bikes when we went to dinner. Nice screened in porch for morning coffee. Excellent location, nice neighbors. Big screen TVs all worked easily! Host was super nice and helpful. Would highly recommend!"
60 STEPS TO BEST BEACH ON THE KEY! PRIVATE HOME ⭐⭐⭐⭐⭐ BEAUTIFUL BOTANICAL GARDEN
On the beach, sun-loungers, beach towels
Spectacular Gulf Front View 1/1 Visitor Unit
10.0 out of 10, Exceptional, (95)
"We had a wonderful time! The views are spectacular! And the unit was so much better than pictured! Very clean and comfortable. We brought our dog and he loved it too! Highly recommend it!!"
The price is NZ$650
per night
30 May - 31 May
Spectacular Gulf Front View 1/1 Visitor Unit
Property grounds
North Port Escape w/ Pool ~ 12 Mi to Beach!
10.0 out of 10, Exceptional, (3)
"The property manager was excellent"
North Port Escape w/ Pool ~ 12 Mi to Beach!
Fridge, microwave, oven, stovetop
Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!
9.6 out of 10, Exceptional, (10)
"If you’re looking for a budget friendly beach vacation, this is a great spot!"
The price is NZ$404
per night
1 Jun - 2 Jun
Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!
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See all available properties in Little 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.

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

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!!
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!
2 outdoor pools, open 8:00 AM to 8:30 PM, pool cabanas (surcharge)
Sunseeker Resort Charlotte Harbor
4.0 star property
9.4 out of 10, Exceptional, (231)
"Friendliness, clean, new"
The price is NZ$341
per night
28 May - 29 May
Sunseeker Resort Charlotte Harbor
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Little Gasparilla Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Little Gasparilla Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Little Gasparilla Island. Seeing all the best attractions is bound to make you fall in love with Little Gasparilla Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Little Gasparilla Island short-term rentals, that won’t be hard to do.

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