Little Gasparilla Island Vacation Rentals

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Our top choices for Little Gasparilla Island vacation rentals

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,204 reviews)
"We had a great stay!!"
United States
Rebecca
The price is CA $262
CA $293 total
includes taxes & fees
Jun 9 - Jun 10
The Suites at Fishermen’s Village- 2 Bedroom Suites

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (277 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is CA $161
CA $182 total
includes taxes & fees
May 19 - May 20
Kon Tiki Inn

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (287 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is CA $139
CA $362 total
includes taxes & fees
May 21 - May 22
Matlacha Tiny Village

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is CA $280
CA $558 total
includes taxes & fees
May 25 - May 26
MALU LANI Inn & Marina

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is CA $158
CA $795 total
includes taxes & fees
May 18 - May 19
Chadwick Cove Resort & Marina

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is CA $254
CA $639 total
includes taxes & fees
May 18 - May 19
Myakka River

Beach house

Beach house
Manasota Key
10.0 out of 10, Exceptional, (36 reviews)
"Great property. Great hosts. "
United States
Nick B.
The price is CA $337
CA $687 total
includes taxes & fees
May 18 - May 19
Beach house

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)
"Couldn’t been better"
United States
Louis
The price is CA $206
CA $433 total
includes taxes & fees
May 18 - May 19
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
9.8 out of 10, Exceptional, (40 reviews)
"Very private beach. Beautiful lodging and everything you need to have a great beach vacation. The host was wonderful and answered questions quickly. The whole package for a memorable vacation. "
United States
Anonymous traveller
The price is CA $756
CA $1,391 total
includes taxes & fees
May 23 - May 24
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (48 reviews)
"Cute home that was perfect to spend time there as well as go sightseeing. If you stay here be sure to go down to the end of the street to meet UNO.Pictures are very acurate"
United States
Janice F.
The price is CA $235
CA $513 total
includes taxes & fees
Jun 1 - Jun 2
NEW!! The “WATERSIDE” COTTAGE~With dockage

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is CA $118
CA $306 total
includes taxes & fees
May 18 - May 19
Nestled in North Port. Updated 2 Bed / 1 Bath.

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, (7 reviews)
"Everything was great, including the host"
United States
Fred
The price is CA $199
CA $469 total
includes taxes & fees
May 18 - May 19
2-bedroom pool house with golf cart in Englewood, close to the beaches!

Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.4 out of 10, Exceptional, (13 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is CA $184
CA $337 total
includes taxes & fees
May 18 - May 19
Beautiful house with lake view

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife
Bokeelia
9.8 out of 10, Exceptional, (47 reviews)
"Hosts were very helpful and informative. Clean and well equipped house. We loved the pool and hot tub!"
United States
Rosemary L.
The price is CA $275
CA $642 total
includes taxes & fees
Jun 1 - Jun 2
Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart

Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart
North Captiva
10.0 out of 10, Exceptional, (24 reviews)
"The location and accommodations were perfect for our full family getaway! The beach had an abundance of shells and wildlife - we really enjoyed our time together at Sunny By You Beach House!"
United States
Rebekah R.
The price is CA $618
CA $1,809 total
includes taxes & fees
May 18 - May 19
Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart

Beachfront Palace with Birdseye Rooftop Deck!

Beachfront Palace with Birdseye Rooftop Deck!
Manasota Beach
9.8 out of 10, Exceptional, (20 reviews)
"Everything was absolutely terrific from the second we checked in till we left "
United States
Chris N.
The price is CA $547
CA $1,046 total
includes taxes & fees
May 31 - Jun 1
Beachfront Palace with Birdseye Rooftop Deck!

Island Retreat Private Pool + Cart | Green Tortuga

Island Retreat Private Pool + Cart | Green Tortuga
North Captiva
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful location and beautiful home!"
United States
Susan P.
The price is CA $516
CA $1,694 total
includes taxes & fees
May 18 - May 19
Island Retreat Private Pool + Cart | Green Tortuga

Gulf Front Escape at a Beach Resort, Pet Friendly

Gulf Front Escape at a Beach Resort, Pet Friendly
Manasota Beach
9.2 out of 10, Wonderful, (5 reviews)
"We absolutely loved the ocean view, and the proximity to both the beach and parking was incredibly convenient. The beach house itself was charming and cozy—perfect for a relaxing getaway. We would definitely stay here again in the future."
United States
Velnet P.
The price is CA $440
CA $1,029 total
includes taxes & fees
May 24 - May 25
Gulf Front Escape at a Beach Resort, Pet Friendly

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, (4 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 $216
CA $592 total
includes taxes & fees
May 31 - Jun 1
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Manasota Key -Your Piece of Paradise - Steps to beach

Manasota Key -Your Piece of Paradise - Steps to beach
Manasota Key
9.8 out of 10, Exceptional, (11 reviews)
"Great host! Dan made sure My stay was perfect!Master suite even has a view of the GulfWould definitely stay again and recommend "
United States
Jim R.
The price is CA $441
CA $661 total
includes taxes & fees
Jun 4 - Jun 5
Manasota Key -Your Piece of Paradise - Steps to beach
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 Little Gasparilla Island Hotel Reviews

Find out more about Little Gasparilla Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.