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Our top choices for Gasparilla Island villas
1. Matlacha Tiny Village
Matlacha Tiny VillageMatlacha
9.0 out of 10, Wonderful, (299 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
Shannon
The price is HK$1,037
HK$1,745 total
includes taxes & fees
10 Nov - 11 Nov
2. 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, (47 reviews)
"I travel down South for business every so often and I'm always looking for a nice spot to stay. This place was great and extremely clean. Heather was great with responding to any questions I had. A lot of fun restaurants and local bars within less than a mile. I will be back."
John M.
The price is HK$1,321
HK$2,892 total
includes taxes & fees
17 Nov - 18 Nov
3. Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Water Front Boundary Vacation Home Villa close to beaches, golfing, FishingOakland Hills
9.8 out of 10, Exceptional, (78 reviews)
"Great hosts and great stay! Would highly recommend."
Kerry M.
The price is HK$840
HK$2,650 total
includes taxes & fees
10 Nov - 11 Nov
4. Seashell Shanty at The Beach Shack! Come On Down!
Seashell Shanty at The Beach Shack! Come On Down!Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place and a great location "
Matthew C.
The price is HK$1,321
HK$2,892 total
includes taxes & fees
12 Nov - 13 Nov
5. Waterview Vacation Retreat Close To Ocean
Waterview Vacation Retreat Close To OceanOakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"The property was great for 3 adults on a golf trip."
Lisa D.
The price is HK$953
HK$2,784 total
includes taxes & fees
10 Nov - 11 Nov
6. 3BR Boundary Breeze Heated Pool Beach Golf Nearby
3BR Boundary Breeze Heated Pool Beach Golf NearbyOakland Hills
10.0 out of 10, Exceptional, (3 reviews)
"Clean. Fast communication. Lots of space for our stay. Will stay again next time we drive down for the weekend!"
Catherine P.
The price is HK$1,122
HK$2,989 total
includes taxes & fees
10 Nov - 11 Nov
7. Flamingo's Nest at the Beach Shack. Just one block from the beach!
Flamingo's Nest at the Beach Shack. Just one block from the beach!Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"Location was great, property condition is excellent!"
Mabel
The price is HK$1,321
HK$2,892 total
includes taxes & fees
10 Nov - 11 Nov
8. Stunning Villa in Golfer's Paradise/Canal Views
Stunning Villa in Golfer's Paradise/Canal ViewsLong Meadow
9.6 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay. Beautiful house with plenty of space. Enjoyed lanai with great sunsets. Would stay again."
Carol C.
The price is HK$1,185
HK$4,001 total
includes taxes & fees
10 Nov - 11 Nov
9. "Sea Dunes" 3 bedrooms 2 bath
"Sea Dunes" 3 bedrooms 2 bathPort Charlotte
7.4 out of 10, Good, (3 reviews)
"For our purposes, shopping and other activities were close enough. "
Charles H.
The price is HK$604
HK$3,015 total
includes taxes & fees
10 Nov - 11 Nov
10. Lake Marlin Villa 2
Lake Marlin Villa 2Englewood East
10.0 out of 10, Exceptional, (20 reviews)
"House was very clean and the location was just what we were looking for. "
Maria K.
The price is HK$855
HK$1,586 total
includes taxes & fees
10 Nov - 11 Nov
11. Beautiful house with lake view
Beautiful house with lake viewEnglewood East
9.6 out of 10, Exceptional, (17 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
Amara D.
The price is HK$847
HK$1,577 total
includes taxes & fees
10 Nov - 11 Nov
12. Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf BeachesEnglewood South
10.0 out of 10, Exceptional, (4 reviews)
"This was a wonderful vacation! The house was perfect! Very clean and decorated beautifully! We had everything that we needed! Great location too! We would recommend this house to anyone coming to Englewood, it was wonderful! We will be coming back! Thank you for sharing your beautiful house with us!!"
Lisa M.
The price is HK$1,207
HK$3,371 total
includes taxes & fees
10 Nov - 11 Nov
13. Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, FishingPebble Beach
9.6 out of 10, Exceptional, (4 reviews)
"The house was beautiful and lived up to the pictures. The hosts were responsive and very helpful during our stay. We were so happy to rent for a month and be able to bring our dog. Thank you so much!"
Deborah M.
The price is HK$1,231
HK$2,921 total
includes taxes & fees
16 Nov - 17 Nov
14. Waterview Villa With Heated Pool
Waterview Villa With Heated PoolOakland Hills
10.0 out of 10, Exceptional, (1 review)
"Our host was very good at responding to our questions. The home was great! Very clean with everything you could need."
Barbara H.
The price is HK$1,192
HK$3,068 total
includes taxes & fees
10 Nov - 11 Nov
15. Seaglass Inn at the Beach Shack Just one block from the beach!
Seaglass Inn at the Beach Shack Just one block from the beach!Manasota Key
10.0 out of 10, Exceptional, (28 reviews)
"The Seaglass Inn was perfect for our weekend stay with the family. The location was great, and the place had everything we needed and then some. The beach was a quick walk away and beautiful! We would definitely book here again in the future. "
erika b.
The price is HK$1,820
HK$3,824 total
includes taxes & fees
10 Nov - 11 Nov
16. The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor KitchenPort Charlotte
9.8 out of 10, Exceptional, (22 reviews)
"The house was great, the pool terrific. Our family enjoyed time together. Thank you."
Marlo S.
The price is HK$1,999
HK$5,210 total
includes taxes & fees
10 Nov - 11 Nov
17. Pineapple Express at the Beach Shack Just one block from the beach!
Pineapple Express at the Beach Shack Just one block from the beach!Manasota Key
10.0 out of 10, Exceptional, (38 reviews)
"Everything you could want or need was available!Excellent location!Heather was amazing to work with!"
lisa w.
The price is HK$1,820
HK$3,824 total
includes taxes & fees
10 Nov - 11 Nov
18. Massive Cali King Villa | Heated Saltwater Pool
Massive Cali King Villa | Heated Saltwater PoolPelican
9.6 out of 10, Exceptional, (24 reviews)
"100% recommended for a family vacation!"
Tommy P.
The price is HK$1,380
HK$3,792 total
includes taxes & fees
15 Nov - 16 Nov
19. Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View
Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal ViewTrafalgar
9.2 out of 10, Wonderful, (35 reviews)
"Such a beautiful house! We had a great time, everything was 10/10!"
Amy B.
The price is HK$2,152
HK$5,875 total
includes taxes & fees
1 Dec - 2 Dec
20. Casa del Lago: Relaxing Waterfront Pool House
Casa del Lago: Relaxing Waterfront Pool HouseMariner
The price is HK$2,744
HK$4,859 total
includes taxes & fees
10 Nov - 11 Nov
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.
Learn more about Gasparilla Island
Pristine beaches and the historic Port Boca Grande Lighthouse beckon visitors to this Gulf Coast gem. Rent a bike to explore charming Boca Grande, or cast a line for tarpon in the island's world-renowned fishing spots.
Photo by Dan Rose
Open Photo by Dan Rose