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

Holiday Homes in Gasparilla Island

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Our top choices for Gasparilla Island holiday 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 NZ$639
includes taxes & fees
20 Aug - 21 Aug
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 NZ$593
includes taxes & fees
20 Aug - 21 Aug
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 NZ$590
includes taxes & fees
20 Aug - 21 Aug
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 NZ$665
includes taxes & fees
1 Sept - 2 Sept
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 NZ$584
includes taxes & fees
20 Aug - 21 Aug
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 NZ$390
includes taxes & fees
17 Sept - 18 Sept
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 NZ$2,140
includes taxes & fees
20 Aug - 21 Aug
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 NZ$605
includes taxes & fees
20 Aug - 21 Aug
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 NZ$723
includes taxes & fees
25 Aug - 26 Aug
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 NZ$667
includes taxes & fees
25 Aug - 26 Aug
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 NZ$863
includes taxes & fees
25 Aug - 26 Aug
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 NZ$552
includes taxes & fees
1 Sept - 2 Sept
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 NZ$847
includes taxes & fees
20 Aug - 21 Aug
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 NZ$450
includes taxes & fees
6 Sept - 7 Sept
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 NZ$543
includes taxes & fees
24 Aug - 25 Aug
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 NZ$420
includes taxes & fees
20 Aug - 21 Aug
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 NZ$841
includes taxes & fees
20 Aug - 21 Aug
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 NZ$363
includes taxes & fees
22 Aug - 23 Aug
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 NZ$552
includes taxes & fees
1 Sept - 2 Sept
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 NZ$439
includes taxes & fees
25 Aug - 26 Aug
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 Holiday Homes information

Number of reviews
349
Accommodation
1239 Holiday Homes
Lowest Price
NZ$363
Highest Price
NZ$2,140

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