A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

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Our top choices for Gasparilla Island vacation homes

1. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
The price is ¥16,057
¥58,596 total
includes taxes & fees
Aug 24 - Aug 25
Casa Florida 🌴 waterfront home with boat ramp

2. WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (29 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is ¥17,374
¥56,960 total
includes taxes & fees
Aug 21 - Aug 22
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

3. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (29 reviews)
"The property was very clean and conveniently located. "
United States
Chris F.
The price is ¥14,098
¥56,659 total
includes taxes & fees
Aug 27 - Aug 28
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

4. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (51 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
The price is ¥27,288
¥59,210 total
includes taxes & fees
Sep 2 - Sep 3
NEW!! The “WATERSIDE” COTTAGE~With dockage

5. WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Oakland Hills
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is ¥16,804
¥56,162 total
includes taxes & fees
Aug 31 - Sep 1
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

6. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is ¥11,867
¥38,355 total
includes taxes & fees
Aug 24 - Aug 25
Charming 2-bedroom house in Englewood with WiFi and AC

7. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva
10.0 out of 10, Exceptional, (35 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is ¥20,554
¥210,392 total
includes taxes & fees
Aug 21 - Aug 22
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

8. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Oakland Hills
10.0 out of 10, Exceptional, (36 reviews)
"Very clean and served out brief visit well."
United States
Patricia M.
The price is ¥18,371
¥57,603 total
includes taxes & fees
Aug 31 - Sep 1
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

9. 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, (10 reviews)
"We had a wonderful stay. Beautiful home with a peaceful view. Great communication with the host. A nice quiet neighborhood. Would stay again. "
United States
Shauna
The price is ¥25,094
¥68,717 total
includes taxes & fees
Aug 26 - Aug 27
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

10. Rotonda Retreat with Heated Pool, Golf, Beaches!

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (21 reviews)
"We really enjoyed this property!! "
United States
laura k.
The price is ¥11,867
¥62,944 total
includes taxes & fees
Aug 23 - Aug 24
Rotonda Retreat with Heated Pool, Golf, Beaches!

11. Golf & Beach Retreat Firepit BBQ Near Boca Grande

Golf & Beach Retreat Firepit BBQ Near Boca Grande
Oakland Hills
10.0 out of 10, Exceptional, (6 reviews)
"Great house and place to stay"
United States
Mike C.
The price is ¥24,779
¥81,235 total
includes taxes & fees
Aug 24 - Aug 25
Golf & Beach Retreat Firepit BBQ Near Boca Grande

12. South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests

South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Oakland Hills
9.6 out of 10, Exceptional, (5 reviews)
"This was the perfect location for our stay. It was clean, comfortable, and well equipped."
United States
Dorian D.
The price is ¥15,032
¥52,976 total
includes taxes & fees
Sep 3 - Sep 4
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests

13. HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful place to stay. Great location in close proximity to restaurants, shopping and the beach. Would certainly choose this home again."
United States
Brenda W.
The price is ¥15,823
¥73,957 total
includes taxes & fees
Aug 21 - Aug 22
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

14. 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, (10 reviews)
"Great stay, great host, and a great time!"
United States
Christopher G.
The price is ¥15,958
¥43,374 total
includes taxes & fees
Sep 6 - Sep 7
2-bedroom pool house with golf cart in Englewood, close to the beaches!

15. Cozy Modern Home - Walkable - 10 Min to Beach

Cozy Modern Home - Walkable - 10 Min to Beach
Englewood East
9.8 out of 10, Exceptional, (8 reviews)
"The home was cozy and friendly. I unfortunately had to leave early but for the time I spent it was great! "
United States
Oscar J.
The price is ¥9,399
¥51,824 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Modern Home - Walkable - 10 Min to Beach

16. Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.4 out of 10, Exceptional, (6 reviews)
"Great little spot!"
United States
Matthew
The price is ¥9,826
¥39,673 total
includes taxes & fees
Aug 21 - Aug 22
Path to Paradise.

17. Large house with heated walk-in pool near beaches!

Large house with heated walk-in pool near beaches!
Pinehurst
8.6 out of 10, Excellent, (22 reviews)
"Excellent place"
United States
Jeanne I.
The price is ¥23,341
¥79,467 total
includes taxes & fees
Aug 26 - Aug 27
Large house with heated walk-in pool near beaches!

18. Tranquil and close to Englewood beach

Tranquil and close to Englewood beach
Englewood South
9.8 out of 10, Exceptional, (10 reviews)
"The place is functional, clean, well equipped. Great location for restaurants, shopping. Only a 7 minute drive to Englewood Beach and 15 minutes to Rotunda golf, 5 golf courses. "
United States
Michael J.
The price is ¥12,229
¥34,506 total
includes taxes & fees
Aug 21 - Aug 22
Tranquil and close to Englewood beach

19. Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Oakland Hills
9.8 out of 10, Exceptional, (28 reviews)
"Great alternative to a hotel. Beautiful and clean."
United States
Sadie A.
The price is ¥14,402
¥52,419 total
includes taxes & fees
Sep 2 - Sep 3
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

20. Snowbirds escape / vacation gateway

Snowbirds escape / vacation gateway
Englewood East
8.8 out of 10, Excellent, (15 reviews)
"Host was very fast to respond, understanding, and accommodating. Pool is offsite but we spent our time at the beach. Overall satisfied and would stay again."
United States
Logan C.
The price is ¥16,946
¥41,449 total
includes taxes & fees
Aug 21 - Aug 22
Snowbirds escape / vacation gateway
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 Gasparilla Island Hotel Reviews

Find out more about Gasparilla Island

Gasparilla Island Vacation Homes information

Number of reviews
349
Accommodation
1291 Vacation Homes
Lowest Price
¥34,506
Highest Price
¥210,392

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