Photo by Dan Rose

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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 AED 602
AED 1,553 total
includes taxes & fees
6 Dec - 7 Dec
Casa Florida 🌴 waterfront home with boat ramp

2. 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 Island
10.0 out of 10, Exceptional, (37 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is AED 339
AED 3,490 total
includes taxes & fees
8 Nov - 9 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

3. 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)
"Everything we needed after a long day of fishing"
United States
WARREN R.
The price is AED 426
AED 1,282 total
includes taxes & fees
19 Nov - 20 Nov
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

4. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AED 345
AED 1,335 total
includes taxes & fees
9 Nov - 10 Nov
Dreams Away - Sleeps 10 Pool Golf Fun

5. 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 AED 393
AED 1,241 total
includes taxes & fees
19 Nov - 20 Nov
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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, (6 reviews)
"The host was so nice I’ll be staying there again!"
United States
Melissa
Charming 2-bedroom house in Englewood with WiFi and AC

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 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 AED 918
AED 1,642 total
includes taxes & fees
8 Nov - 9 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage

8. 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, (19 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 496
AED 1,316 total
includes taxes & fees
6 Dec - 7 Dec
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

9. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
The price is AED 384
AED 900 total
includes taxes & fees
6 Nov - 7 Nov
Nautical Nook

10. Three Bedroom home with heated pool!

Three Bedroom home with heated pool!
Broadmoor
9.6 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay"
United States
Julia H.
Three Bedroom home with heated pool!

11. Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AED 441
AED 972 total
includes taxes & fees
4 Dec - 5 Dec
Old Floridian cottage in Historic Gulf Village

12. 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, (11 reviews)
"Great property, very clean and host was extremely helpful. Great quiet neighborhood with friendly neighbors."
United States
Neal G.
The price is AED 680
AED 1,633 total
includes taxes & fees
19 Nov - 20 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

13. 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 AED 471
AED 1,311 total
includes taxes & fees
6 Nov - 7 Nov
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

14. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Oakland Hills
10.0 out of 10, Exceptional, (14 reviews)
"We will be booking again. it was perfect for us! very clean and everything you need to be comfortable."
United States
Kristen A.
The price is AED 534
AED 1,344 total
includes taxes & fees
6 Nov - 7 Nov
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

15. HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Clean, comfortable, has everything you need for a vacation"
United States
Rick J.
The price is AED 441
AED 1,715 total
includes taxes & fees
19 Nov - 20 Nov
HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

16. Newly renovated cozy 2 Bedroom.

Newly renovated cozy 2 Bedroom.
Englewood East
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful place for long or short term stay. Perfectly located for the beach, shopping and restaurants!!"
United States
Shari F.
The price is AED 264
AED 759 total
includes taxes & fees
9 Nov - 10 Nov
Newly renovated cozy 2 Bedroom.

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

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (23 reviews)
"This was our second year staying here, and once again everything was absolutely perfect. The house was spotless, comfortable, and very well maintained. Check-in was smooth, communication was excellent, and everything was exactly as expected. We truly enjoyed our stay and felt right at home. We would happily come back again and highly recommend this place. Thank you for another wonderful stay!"
United States
Cesar C.
The price is AED 367
AED 1,604 total
includes taxes & fees
9 Nov - 10 Nov
Rotonda Retreat with Heated Pool, Golf, Beaches!

18. 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 AED 496
AED 1,694 total
includes taxes & fees
19 Nov - 20 Nov
Golf & Beach Retreat Firepit BBQ Near Boca Grande

19. 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 AED 459
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov
2-bedroom pool house with golf cart in Englewood, close to the beaches!

20. Pelican Paradise- Pets Welcome!

Pelican Paradise- Pets Welcome!
Englewood East
The price is AED 311
AED 1,162 total
includes taxes & fees
8 Nov - 9 Nov
Pelican Paradise- Pets Welcome!
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.

A tall white lighthouse with a metal framework, surrounded by palm trees and greenery.
Photo by Dan Rose
Open Photo by Dan Rose

Top reviews in Gasparilla Island

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