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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Gasparilla Island condo rentals

An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

1. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
$559 nightly
The price is $602
Oct 2 - Oct 3
Total with taxes and fees
Chadwick Cove Resort & Marina
A waterfront patio with Adirondack chairs, a fire pit, and a grill area.

2. Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (9 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
$130 nightly
The price is $143
Sep 30 - Oct 1
Total with taxes and fees
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
A marina at sunset with boats docked, wooden piers, and buildings in the background.

3. Luxury Waterfront Escape | Love the Marina View!

Luxury Waterfront Escape | Love the Marina View!
Burnt Store Marina
$795 nightly
The price is $889
Sep 30 - Oct 1
Total with taxes and fees
Luxury Waterfront Escape | Love the Marina View!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of the beach and ocean.

4. Bayfront Condo, Prime Beach Access, Manasota Key

Bayfront Condo, Prime Beach Access, Manasota Key
Manasota Key
9.4 out of 10, Exceptional, (16 reviews)
"Excellent place to stay! Would definitely stay again."
United States
Justin B.
$315 nightly
The price is $350
Sep 30 - Oct 1
Total with taxes and fees
Bayfront Condo, Prime Beach Access, Manasota Key
Marina

5. Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
$397 nightly
The price is $410
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access
A beach with clear turquoise water and a clear sky.

6. Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck

Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
Manasota Key
$390 nightly
The price is $434
Sep 30 - Oct 1
Total with taxes and fees
Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
A covered porch with two Adirondack chairs and a garage door.

7. Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)

Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
Manasota Key
$390 nightly
The price is $434
Sep 30 - Oct 1
Total with taxes and fees
Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
A beach with a clear view of the water, a wooden walkway, and a palm tree.

8. Waterfront Condo w/Private Beach on Manasota Key!

Waterfront Condo w/Private Beach on Manasota Key!
Manasota Key
$480 nightly
The price is $498
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Condo w/Private Beach on Manasota Key!
A multi-story hotel with balconies, a palm tree, and a picnic table.

9. Bayfront Condo w/Private Beach on Manasota Key - Unit 311

Bayfront Condo w/Private Beach on Manasota Key - Unit 311
Manasota Key
$477 nightly
The price is $495
Sep 30 - Oct 1
Total with taxes and fees
Bayfront Condo w/Private Beach on Manasota Key - Unit 311
A bedroom with two beds, a window, wooden ceiling beams, and a small bedside table with a lamp.

10. Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool

Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool
Manasota Key
$254 nightly
The price is $282
Oct 19 - Oct 20
Total with taxes and fees
Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool
A waterfront patio with Adirondack chairs, a fire pit, and a grill area.

11. 1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!

1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!
Burnt Store
$180 nightly
The price is $198
Sep 30 - Oct 1
Total with taxes and fees
1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!
A waterfront patio with Adirondack chairs, a fire pit, and a grill area.

12. Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!

Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!
Matlacha
7.4 out of 10, Good, (3 reviews)
"Great little place, nice and clean quiet. I'm so close to everything puk de gorda.Cape coral natalche saint james city, just beautiful, tropical great place to see the sunrise on the back.Dock."
United States
MICHAEL L.
$130 nightly
The price is $143
Sep 30 - Oct 1
Total with taxes and fees
Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!
A beach with a palm tree, a wooden walkway, and a view of the water and distant buildings.

13. Bayfront Condo with Private Beach - Unit 313

Bayfront Condo with Private Beach - Unit 313
Manasota Key
$480 nightly
The price is $498
Sep 30 - Oct 1
Total with taxes and fees
Bayfront Condo with Private Beach - Unit 313
A beach with kayaks and a boat on a sandy shore.

14. Private Beach, Fishing Dock & Heated Pool Paradise

Private Beach, Fishing Dock & Heated Pool Paradise
Port Charlotte
8.8 out of 10, Excellent, (6 reviews)
"We enjoyed our stay!"
United States
Penny C.
$767 nightly
The price is $799
Oct 2 - Oct 3
Total with taxes and fees
Private Beach, Fishing Dock & Heated Pool Paradise
A beach with clear water, a person walking, and a tree in the foreground.

15. Cozy Coastal Quadruplex on Manasota Key, Entire Property Rental, Sleeps 12

Cozy Coastal Quadruplex on Manasota Key, Entire Property Rental, Sleeps 12
Manasota Key
$1,069 nightly
The price is $1,189
Sep 30 - Oct 1
Total with taxes and fees
Cozy Coastal Quadruplex on Manasota Key, Entire Property Rental, Sleeps 12
An aerial view of a coastal resort with beachfront properties, a marina, and a marina with boats.

16. 3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (98 reviews)
"Great place and will definitely stay here again."
United States
Jessica S.
$482 nightly
The price is $536
Oct 5 - Oct 6
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
A spacious living area with a kitchen, a dining area, and a view of the ocean.

17. 3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf

3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (85 reviews)
"Wish we could have stayed longer We will definitely be back"
United States
Kendra
$504 nightly
The price is $561
Oct 5 - Oct 6
Total with taxes and fees
3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
A modern kitchen with white cabinetry, a central island, and a dining area with a sofa and table.

18. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
$506 nightly
The price is $561
Sep 30 - Oct 1
Total with taxes and fees
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Marina

19. Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (24 reviews)
"Nice place to stay "
United States
Jon L.
$394 nightly
The price is $407
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access
A coastal resort with a long sandy beach, multiple white buildings, and lush greenery.

20. Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
Captiva
9.0 out of 10, Wonderful, (19 reviews)
"Great villa for 2 people. The place was clean, well stocked and comfortable. The pool was lovely. Check in / check out was seamless. Would definitely book again."
United States
Connie A.
$490 nightly
The price is $543
Sep 30 - Oct 1
Total with taxes and fees
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

10/10 Excellent
"Weekend family get together at the resort, the room was impecable, level blue rooftop pool was incredible, service and attention was on point. Harbor yards food hall was amazing, delicious food. Had dinner at the Stretto delicious. The resort was unbelievable we are planning our next stay already."
Maria 2-night trip
Posted 2 hours ago
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Find out more about Gasparilla Island

Gasparilla Island Condo Rentals information

Number of reviews
230
Accommodation
199 Condo Rentals
Lowest Price
$143
Highest Price
$1,189

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