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

Search Condos in Gasparilla Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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, (31 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
The price is ￥22,695
￥96,806 total
includes taxes & fees
Oct 19 - Oct 20
Chadwick Cove Resort & Marina
A spacious living room with a flat-screen TV, a sofa, a coffee table, and a balcony with a view of the beach.

2. Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
9.0 out of 10, Wonderful, (16 reviews)
"Clean property, easy access. Good kitchen supplies. It was nice to be staying on the island and close to the beach."
United States
Louis
The price is ￥16,425
￥72,764 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
A waterfront patio with Adirondack chairs, a fire pit, and a grill area.

3. 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.
The price is ￥10,292
￥25,236 total
includes taxes & fees
Oct 15 - Oct 16
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
A spacious living area with a kitchen, a dining area, and a view of the ocean.

4. 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, (87 reviews)
"Wish we could have stayed longer We will definitely be back"
United States
Kendra
The price is ￥31,351
￥72,323 total
includes taxes & fees
Oct 17 - Oct 18
3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
A bedroom with two beds, a window, wooden ceiling beams, and a small bedside table with a lamp.

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

Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool
Manasota Key
The price is ￥9,536
￥46,058 total
includes taxes & fees
Oct 19 - Oct 20
Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool
A wooden dock with a bench and metal bollards, leading to calm turquoise waters.

6. Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Manasota Key
9.8 out of 10, Exceptional, (52 reviews)
"The place was very lovely! Just enough room to be comfortable and a close walk to the beach."
United States
Jess C.
The price is ￥18,244
￥54,731 total
includes taxes & fees
Oct 18 - Oct 19
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Marina

7. 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.
The price is ￥20,782
￥74,103 total
includes taxes & fees
Oct 19 - Oct 20
Waterfront Condo Walkable to Everything with Beach Access
A wooden pathway leading to a building with a white exterior and a view of the water.

8. Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock

Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock
Manasota Key
9.8 out of 10, Exceptional, (22 reviews)
The price is ￥19,962
￥85,826 total
includes taxes & fees
Oct 19 - Oct 20
Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock
A waterfront patio with Adirondack chairs, a fire pit, and a grill area.

9. 1-Bedroom Condo with Waterview Patio Angel's Den - 1-Bedroom Condo with Waterview Patio Angel

1-Bedroom Condo with Waterview Patio Angel's Den - 1-Bedroom Condo with Waterview Patio Angel
Matlacha
8.8 out of 10, Excellent, (3 reviews)
"Well kept for and very clean and comfortable ! Stayed one night on the way to North Captiva Island! We enjoyed everything about our stay!"
United States
Kevin C.
The price is ￥14,251
￥32,457 total
includes taxes & fees
Oct 15 - Oct 16
1-Bedroom Condo with Waterview Patio Angel's Den - 1-Bedroom Condo with Waterview Patio Angel
An aerial view of a coastal resort with beachfront properties, a marina, and a marina with boats.

10. 3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf

3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (78 reviews)
"The property was very clean and had an excellent location for the beach. The parking is a little tight but they can make accommodations if needed. The unit we stayed in all had views of the beach and balconies. This place is amazing. I will definitely stay there again and highly recommended it."
United States
Dawn
The price is ￥31,411
￥74,206 total
includes taxes & fees
Oct 18 - Oct 19
3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
Beach

11. Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach

Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach
Captiva
8.6 out of 10, Excellent, (9 reviews)
"My husband and I enjoyed our stay here. The location was perfect, with restaurants and shops being within easy walking distance. The pool was beautiful and never crowded. "
United States
Maureen J.
The price is ￥25,018
￥81,718 total
includes taxes & fees
Oct 15 - Oct 16
Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach
A coastal resort with a long sandy beach, multiple white buildings, and lush greenery.

12. 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.
The price is ￥26,443
￥92,149 total
includes taxes & fees
Oct 15 - Oct 16
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
A resort with multiple buildings, a marina, and a parking lot.

13. Bayside Villas 5142: Panoramic Water Views & Coastal Elegance in Captiva

Bayside Villas 5142: Panoramic Water Views & Coastal Elegance in Captiva
Captiva
7.0 out of 10, Good, (2 reviews)
"Property was very nice and clean and store were very close by it was a pleasure staying there . Looking forward to doing it again"
United States
David M.
The price is ￥21,036
￥79,634 total
includes taxes & fees
Oct 21 - Oct 22
Bayside Villas 5142: Panoramic Water Views & Coastal Elegance in Captiva
A coastal hotel with beachfront access, multiple buildings, and a clear view of the ocean.

14. Captiva Villa 3115 | Upscale Residence | Great Amenities | Walk to the Beach

Captiva Villa 3115 | Upscale Residence | Great Amenities | Walk to the Beach
Captiva
7.2 out of 10, Good, (10 reviews)
"Great stay - everything was fantastic."
United States
Tim S.
The price is ￥22,009
￥76,728 total
includes taxes & fees
Oct 15 - Oct 16
Captiva Villa 3115 | Upscale Residence | Great Amenities | Walk to the Beach
A beach with clear turquoise water and a clear sky.

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

Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
Manasota Key
The price is ￥20,111
￥71,575 total
includes taxes & fees
Oct 15 - Oct 16
Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
A beach with a clear view of the water, a wooden walkway, and a palm tree.

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

Waterfront Condo w/Private Beach on Manasota Key!
Manasota Key
The price is ￥24,939
￥82,877 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront Condo w/Private Beach on Manasota Key!
A covered porch with two Adirondack chairs and a garage door.

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

Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
Manasota Key
The price is ￥20,111
￥71,575 total
includes taxes & fees
Oct 15 - Oct 16
Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
A beach view with a sandy area, palm trees, and a wooden walkway leading to a dock.

18. Bayfront 2-Bedroom Condo with Private Beach - 314

Bayfront 2-Bedroom Condo with Private Beach - 314
Manasota Key
The price is ￥24,939
￥83,827 total
includes taxes & fees
Oct 21 - Oct 22
Bayfront 2-Bedroom Condo with Private Beach - 314
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of the beach and ocean.

19. Bayfront Condo, Prime Beach Access, Manasota Key

Bayfront Condo, Prime Beach Access, Manasota Key
Manasota Key
9.2 out of 10, Wonderful, (19 reviews)
"Excellent place to stay! Would definitely stay again."
United States
Justin B.
The price is ￥19,381
￥59,390 total
includes taxes & fees
Oct 19 - Oct 20
Bayfront Condo, Prime Beach Access, Manasota Key
A modern kitchen with white cabinetry, a central island, and a dining area with a sofa and table.

20. 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.
The price is ￥25,018
￥95,710 total
includes taxes & fees
Oct 15 - Oct 16
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gasparilla Island Hotel Reviews

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

8/10 Good
"Room itself was clean. Shower needed some attention"
Henry 1-night trip
Posted 10 hours ago
Baymont by Wyndham Punta Gorda/Port Charlotte

Find out more about Gasparilla Island

Gasparilla Island Condo Rentals information

Number of reviews
376
Accommodation
188 Condo Rentals
Lowest Price
￥25,236
Highest Price
￥96,806

Frequently asked questions

Why book your condo in Gasparilla Island with Expedia?
Use Expedia to find your ideal condo in Gasparilla Island. On the lookout for a high-end stay? Make the most of our filters to search for properties with a 5-star rating. If you need to stick to a budget, select how much you want to spend and then browse our fabulous deals. We'll help you find the perfect pad whatever your plans or style of travel.
How can I find cheap condos in Gasparilla Island?
Expedia can help you narrow down your search for cheap condos in Gasparilla Island. To lock in your dream stay in a few clicks, simply use the filter tool to refine your search results by budget, amenities and star rating.

Explore a world of travel with Expedia