Search Gasparilla Island Condo Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Condo Rentals in Gasparilla Island and around

Chadwick Cove Resort & Marina
Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (2)
"Very friendly service!! Jim was amazing ! "
The price is €335
includes taxes & fees
15 Mar - 16 Mar
Chadwick Cove Resort & Marina
Saltwater Serenity - Beachfront, Pool Access, Walk to Restaurants & Live Music
Smart TV

Saltwater Serenity - Beachfront, Pool Access, Walk to Restaurants & Live Music

10.0 out of 10, Exceptional, (1)
"This was, hands down, our best visit and best rental in Manasota. The stairs were a bit daunting at first, but the amazing views made the climb worth the effort. Everything in the unit felt new, fresh and clean. Each of the 3 balconies has a lovely view of the gulf or the bay, so sunrises and sunsets were wonderful. We very much appreciated the pool on the few days where red tide made the beach impossible. Overall, we had such a great time that we have already booked for 2026."
Saltwater Serenity - Beachfront, Pool Access, Walk to Restaurants & Live Music
Sand in Your Toes . . . Right Out Your Front Door!
Property grounds

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (102)
"We found this to be our absolute favorite place yet!! It is PERFECT for us. It was clean and you cannot beat the location. We hope to stay again this time next year. THANK YOU. "
Sand in Your Toes . . . Right Out Your Front Door!
Remodeled Manasota Key Bay Side 1 Bedroom Condo

Remodeled Manasota Key Bay Side 1 Bedroom Condo

3.5 star property
9.2 out of 10, Wonderful, (57)
"Had everything we needed and how close it was to the beach was perfect!"
Remodeled Manasota Key Bay Side 1 Bedroom Condo
Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6
TV, offices

Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6

9.6 out of 10, Exceptional, (7)
"We had a problem with our stay when we checked in due to issues beyond the property manager's control (water issues). The communication up to that point was great, property was clean, and check in was easy. The property manager was good about moving us and communication through the process was excellent. Thank you for accommodating us."
Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6
Book for 4 nights in Jan and Feb 2025! Rates reflect additional 20% off!
Interior

Book for 4 nights in Jan and Feb 2025! Rates reflect additional 20% off!

3.0 star property
Book for 4 nights in Jan and Feb 2025! Rates reflect additional 20% off!
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
On the beach, sun-loungers, beach towels

DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

9.8 out of 10, Exceptional, (49)
"The apartment is comfortable. The porch overlooking the beach is wonderful . Unfortunately, the damage from the hurricane is up and down the beach and definitely makes the area less desirable. That’s not the fault of the owner . The owner could have been more forthright about the damage though. We were shocked at the devastation. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Stunning Harborview Villa in South Seas
Beach

Stunning Harborview Villa in South Seas

9.0 out of 10, Wonderful, (24)
"Nice accommodations! "
Stunning Harborview Villa in South Seas
Superb Beachfront Residence at South Seas Resort
TV, offices

Superb Beachfront Residence at South Seas Resort

9.0 out of 10, Wonderful, (4)
"The condo had a nice, unobstructed view of the beach. We made all our meals and the kitchen was fully stocked with utensils, new appliances and accessories. Very quiet and less than a minute walk to the beach. We will be back! "
Superb Beachfront Residence at South Seas Resort
Wonderful condo, fabulous view overlooks Marina - Month stay discount
Interior

Wonderful condo, fabulous view overlooks Marina - Month stay discount

9.8 out of 10, Exceptional, (93)
"Next door to marina"
Wonderful condo, fabulous view overlooks Marina - Month stay discount
Perfect Beach stay, Newly Renovated, Excellent Location 600ft 200 steps to Beach
On the beach, sun-loungers, beach towels

Perfect Beach stay, Newly Renovated, Excellent Location 600ft 200 steps to Beach

9.6 out of 10, Exceptional, (64)
"Loved the location as well as accommodations. "
Perfect Beach stay, Newly Renovated, Excellent Location 600ft 200 steps to Beach
Gulf side condo be on the beach in minutes!
Sun-loungers, beach towels

Gulf side condo be on the beach in minutes!

9.2 out of 10, Wonderful, (53)
"Was good"
Gulf side condo be on the beach in minutes!
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Beach nearby, sun-loungers, beach towels

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (74)
"This was our first year in 21 years of us not being able to stay in our “home away from home” on the key due to the mass destruction from both Helene and Milton. We decided to book a last minute vacation back to Manasota Key to have closure from where we have stayed and to recharge from a very cold New England winter. We not only recharged but this condo allowed us to have pure relaxation whether it was on the beach or on the porch in a rocking chair. Everything you need is supplied to you. The...
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Be one of the first guests to enjoy this newly renovated luxury waterfront villa
Property grounds

Be one of the first guests to enjoy this newly renovated luxury waterfront villa

10.0 out of 10, Exceptional, (3)
"This was a great spot and so much better than being in a hotel when traveling for business. Andrew was a great host. We will stay here again for sure! "
Be one of the first guests to enjoy this newly renovated luxury waterfront villa
Manasota Key Condo! Private Beach access.Gulf and Bay views
Outdoor pool, a heated pool

Manasota Key Condo! Private Beach access.Gulf and Bay views

10.0 out of 10, Exceptional, (90)
"This was a wonderful place to stay. The owners were so friendly and helpful. The condo & property were very nicely done & in a great location. We would definitely love to come back!"
Manasota Key Condo! Private Beach access.Gulf and Bay views
Waterfront Condo on Boca Grande-Pure Bliss more photos of remodel coming soon!
A heated pool

Waterfront Condo on Boca Grande-Pure Bliss more photos of remodel coming soon!

10.0 out of 10, Exceptional, (68)
"Our stay was exactly what we were looking for. Maria was great to communicate with and the condo was clean with a great balcony. Perfect for our weekend get-away!"
Waterfront Condo on Boca Grande-Pure Bliss more photos of remodel coming soon!
Stunning Condo Inside / Out Direct Beach Front
On the beach, beach towels

Stunning Condo Inside / Out Direct Beach Front

9.8 out of 10, Exceptional, (59)
"Loved this spot! Host was very accommodating. Can’t wait to go back."
Stunning Condo Inside / Out Direct Beach Front
Boca Grande North 46, Bay & Marina Front - Sleeps 4
Living area

Boca Grande North 46, Bay & Marina Front - Sleeps 4

Boca Grande North 46, Bay & Marina Front - Sleeps 4
Charming Manasota Key duplex with beach access
Aerial view

Charming Manasota Key duplex with beach access

2.0 star property
10.0 out of 10, Exceptional, (1)
"So clean and new everything you need for a Florida getaway just steps from the pool and the beach!"
Charming Manasota Key duplex with beach access
SOUTH SEAS BEACH VILLA 2126
Outdoor dining

SOUTH SEAS BEACH VILLA 2126

9.4 out of 10, Exceptional, (48)
"Great location.....everything easy and beautiful. thank you for a great week!"
SOUTH SEAS BEACH VILLA 2126
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.
Don't see what you're looking for?
See all available properties in Gasparilla Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites
Outdoor pool

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (798)
"Nicely Furnished. Beautiful view. Great walking area and great to sit on the little beach on the harbor. Super friendly staff. Loved it!"
The price is €245
includes taxes & fees
1 Apr - 2 Apr
The Suites at Fishermen’s Village- 2 Bedroom Suites
Chadwick Cove Resort & Marina
Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (2)
"Very friendly service!! Jim was amazing ! "
The price is €335
includes taxes & fees
15 Mar - 16 Mar
Chadwick Cove Resort & Marina
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
Terrace/patio

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (97)
"Thank you for sharing your property with us! We had magnificent views—- including a full double rainbow 😍 the space was comfortable and clean and perfect for a long weekend getaway. We were able to easily access our boat to spend time on Cayo costa, lunch on cabbage key and a dip in the pool at the N. Captiva club. We didn’t need to use the bunk house, but would be perfect if we brought the kids! Thank you!!"
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
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.

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.