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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Gasparilla Island vacation homes

A multi-level house with a white exterior, a staircase, and a deck area.

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
10.0 out of 10, Exceptional, (36 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 377
AED 4,703 total
includes taxes & fees
4 Nov - 5 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

2. 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.
Casa Florida 🌴 waterfront home with boat ramp
A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

3. 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 324
AED 1,208 total
includes taxes & fees
16 Oct - 17 Oct
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
A modern kitchen with a central island, white cabinetry, and pendant lighting.

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 AED 327
AED 1,211 total
includes taxes & fees
16 Oct - 17 Oct
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

5. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AED 502
AED 1,511 total
includes taxes & fees
18 Oct - 19 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink.

6. 2/2 Duplex on CANAL all updated; new furniture,

2/2 Duplex on CANAL all updated; new furniture,
Oakland Hills
9.6 out of 10, Exceptional, (10 reviews)
"awesome place"
United States
Brooke P.
The price is AED 404
AED 1,205 total
includes taxes & fees
29 Oct - 30 Oct
2/2 Duplex on CANAL all updated; new furniture,
An aerial view of a coastal area with several small islands connected by bridges.

7. 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 AED 918
AED 1,712 total
includes taxes & fees
28 Oct - 29 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage
A beach with a clear sky, calm sea, and footprints on the sand.

8. 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)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
Charming 2-bedroom house in Englewood with WiFi and AC
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

9. 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 1,289 total
includes taxes & fees
25 Oct - 26 Oct
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

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)
"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 294
AED 1,519 total
includes taxes & fees
24 Oct - 25 Oct
Rotonda Retreat with Heated Pool, Golf, Beaches!
A modern kitchen with white cabinets, stainless steel appliances, and a marble floor.

11. Canal front new everything near Boca Grande Beach

Canal front new everything near Boca Grande Beach
Oakland Hills
8.4 out of 10, Very good, (6 reviews)
"We stayed for one month. Property was very clean, outside finishing up on storm repairs and completed couple days after we arrived. Safe area away from noise, but close drive to beaches and restaurants."
United States
Kristine G.
The price is AED 367
AED 1,161 total
includes taxes & fees
29 Oct - 30 Oct
Canal front new everything near Boca Grande Beach
A covered outdoor dining area with a table and chairs, large windows, and a ceiling fan.

12. 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.
The price is AED 273
AED 1,488 total
includes taxes & fees
16 Oct - 17 Oct
Three Bedroom home with heated pool!
A beach with footprints in the sand and a cloudy sky.

13. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay and it was perfect for our trip to explore the beaches and parks in the area. Clean spacious and had everything we needed. Very nice owners with extra touches of hospitality! Love this gem and will be back!"
United States
Tracie
The price is AED 384
AED 948 total
includes taxes & fees
19 Oct - 20 Oct
Nautical Nook
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

14. 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)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is AED 515
AED 1,497 total
includes taxes & fees
25 Oct - 26 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

15. 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)
"Very nice stay at a beautiful new home!!"
United States
Nancy H.
The price is AED 474
AED 1,321 total
includes taxes & fees
25 Oct - 26 Oct
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

16. 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 496
AED 1,398 total
includes taxes & fees
16 Oct - 17 Oct
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
A spacious living room with a flat-screen TV, a ceiling fan, and a large window offering a view of the outdoors.

17. 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 918
AED 2,385 total
includes taxes & fees
12 Nov - 13 Nov
HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
A modern kitchen with white cabinets, stainless steel appliances, a large island with bar stools, and a view of a green landscape through the glass door.

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 551
AED 1,833 total
includes taxes & fees
12 Nov - 13 Nov
Golf & Beach Retreat Firepit BBQ Near Boca Grande
An aerial view of a residential neighborhood with houses, lawns, and trees.

19. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is AED 360
AED 1,341 total
includes taxes & fees
16 Oct - 17 Oct
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
A beach with a wide expanse of white seashells covering the sand.

20. New! 2025-built House 4-bedroom 2-bath. 15-20 min to the Beach. Lanai+Game Room

New! 2025-built House 4-bedroom 2-bath. 15-20 min to the Beach. Lanai+Game Room
Oakland Hills
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property in an excellent location. "
United States
Ronald H.
New! 2025-built House 4-bedroom 2-bath. 15-20 min to the Beach. Lanai+Game Room
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

SpringHill Suites by Marriott Punta Gorda Harborside

SpringHill Suites by Marriott Punta Gorda Harborside

10/10 Excellent
"Springhill suites was a great place I stayed a week and enjoyed it very much clean rooms great staff incredible breakfast parking can be a small challenge if area is busy all in all great place."
John 7-night trip
Posted 2 hours ago
SpringHill Suites by Marriott Punta Gorda Harborside

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