Photo by Dan Rose

Holiday Homes in Gasparilla Island

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Check prices for these dates

Our top choices for Gasparilla Island holiday homes

1. 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 AU$1,341
includes taxes & fees
10 Nov - 11 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

2. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AU$522
includes taxes & fees
9 Nov - 10 Nov
Dreams Away - Sleeps 10 Pool Golf Fun

3. 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 AU$570
includes taxes & fees
21 Nov - 22 Nov
Casa Florida 🌴 waterfront home with boat ramp

4. 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 AU$493
includes taxes & fees
17 Nov - 18 Nov
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

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 AU$478
includes taxes & fees
7 Nov - 8 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
The price is AU$345
includes taxes & fees
7 Nov - 8 Nov
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 AU$632
includes taxes & fees
5 Nov - 6 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage

8. 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 AU$384
includes taxes & fees
1 Dec - 2 Dec
Old Floridian cottage in Historic Gulf Village

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, (11 reviews)
"Great property, very clean and host was extremely helpful. Great quiet neighborhood with friendly neighbors."
United States
Neal G.
The price is AU$559
includes taxes & fees
15 Nov - 16 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

10. 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 AU$487
includes taxes & fees
5 Nov - 6 Nov
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

11. 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 AU$351
includes taxes & fees
13 Nov - 14 Nov
Nautical Nook

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

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (22 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 AU$617
includes taxes & fees
12 Nov - 13 Nov
Rotonda Retreat with Heated Pool, Golf, Beaches!

13. Beach town modern cottage 3Bed/2Bath house

Beach town modern cottage 3Bed/2Bath house
Englewood East
10.0 out of 10, Exceptional, (5 reviews)
"Host was responsive . This home was very comfortable, really liked the layout . It was light and airy. A bonus was their chairs Great location to Englewood Beach and several other beaches "
United States
Sandi T.
The price is AU$390
includes taxes & fees
8 Nov - 9 Nov
Beach town modern cottage 3Bed/2Bath house

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 AU$424
includes taxes & fees
16 Nov - 17 Nov
2-bedroom pool house with golf cart in Englewood, close to the beaches!

15. 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 AU$638
includes taxes & fees
5 Nov - 6 Nov
Golf & Beach Retreat Firepit BBQ Near Boca Grande

16. 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 AU$508
includes taxes & fees
5 Nov - 6 Nov
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

17. 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 AU$497
includes taxes & fees
5 Nov - 6 Nov
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

18. 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 AU$630
includes taxes & fees
5 Nov - 6 Nov
HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

19. 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 AU$299
includes taxes & fees
9 Nov - 10 Nov
Newly renovated cozy 2 Bedroom.

20. Chic 3BR, 2BA – Brand New!

Chic 3BR, 2BA – Brand New!
Englewood East
The price is AU$481
includes taxes & fees
5 Nov - 6 Nov
Chic 3BR, 2BA – Brand New!
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

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