Search Condo Rentals in Gasparilla Island

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 114 Condo Rentals in Gasparilla Island with updated reviews, rates, and availability.

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (5)
"Chadwick Cove was recently renovated. The interior is cozy, clean and you have everything you need in the condo. Breakfast in the balcony to watch the sunrise at the bay was a plus."
The price is SAR 478
SAR 2,224 total
includes taxes & fees
28 Apr - 29 Apr
Chadwick Cove Resort & Marina

Beachfront-Vacation on a Tropical Island! Pool and tennis closed at this time

10.0 out of 10, Exceptional, (138)
" Our beach vacation to Palm Island was unforgettable! The condo was gorgeous with stunning ocean views. We loved combing the beach for seashells and shark teeth, turning every walk into a treasure hunt. Playing in the sand and waves was a blast, and the sunsets were breathtaking. It was the perfect mix of adventure and relaxation—can't wait to return!"
Beachfront-Vacation on a Tropical Island! Pool and tennis closed at this time

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

10.0 out of 10, Exceptional, (78)
"We absolutely loved everything about this beach property! We had a perfect stay and definitely plan on returning "
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

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

9.4 out of 10, Exceptional, (104)
"this property is everything it says it is on VRBO. It’s right on the beach. It seems to have been updated recently and has a very pleasing color scheme. The kitchen is generously equipped for any cooking project you might undertake. The pool is small, but was a perfect temperature."
Sand in Your Toes . . . Right Out Your Front Door!

Chillax on the Beach or by the Bay!

9.8 out of 10, Exceptional, (14)
"The property was very clean and was big enough for what we were looking for. We are a family of 6 and were looking for a place that gave us easy access to the beach as well as enough room for us all. I would stay here again for my future trips there."
Chillax on the Beach or by the Bay!

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

9.8 out of 10, Exceptional, (50)
"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!

The Summer Wind @ Manasota Key

10.0 out of 10, Exceptional, (9)
"This place is so far removed from the commercial rhetoric, feels like the original low key Florida lifestyle! Beautiful condo, well equipped, the owners are very quick to respond and are great to work with. The hurricane rebuild is still going on, but I would rate this place 5 STARS, without hesitation."
The Summer Wind @ Manasota Key

Remodeled Manasota Key Bay Side 1 Bedroom Condo

3.5 star property
9.2 out of 10, Wonderful, (58)
"GREAT: the host was very accommodating by providing 100% cotton bedding at our request right away!BAD: We rented this property because it offered a full kitchen. However, we were not able to use the oven at all as it had white cleaning stuff residue on all oven walls. We asked the host to get it cleaned, but it was never done during our 10 nights stay ."
Remodeled Manasota Key Bay Side 1 Bedroom Condo

South seas beach villa 2428

9.6 out of 10, Exceptional, (27)
"We have enjoyed many visits to Captiva Island but this was first since Hurricane Ian. Our unit was in wonderful condition - very attractive and well-supplied with kitchen equipment. We planned to mostly eat in given that not as many restaurants are up and running. We spent our days walking the beach and closely observing the osprey pair on their nest and their favorite perching tree right next to our screened porch."
South seas beach villa 2428

APRIL 25% Discount — for 14 days or more! Relax in the Florida Sunshine!

10.0 out of 10, Exceptional, (7)
"Comfortable condo in sunny Florida. Enjoyed beaches that were 15 minutes away. Located close to shopping and groceries. Quiet condo and nice people!"
APRIL 25% Discount — for 14 days or more! Relax in the Florida Sunshine!

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

Ultra Luxe Beach Villa at South Seas Resort

9.6 out of 10, Exceptional, (13)
"Lots of work going on in area but still pleasant stay. Everything was new or redone in unit. Great views for ocean from deck and pool."
Ultra Luxe Beach Villa at South Seas Resort

Amazing New 2/2 Boca Grande North Condo Upstairs, Big Screens and Big Views

10.0 out of 10, Exceptional, (1)
"The condo was great - brand new and stocked with every convenience. Fully stocked kitchen with complimentary beverages. Washer and dryer, big nice new showers, comfy beds, beautiful screened in porch overlooking the water. Fast wifi, nice Samsung frame TV in the living area. The owner was super nice, available and responsive. Would definitely stay there again. "
Amazing New 2/2 Boca Grande North Condo Upstairs, Big Screens and Big Views

SOUTH SEAS BAYSIDE Villa 5310

8.4 out of 10, Very Good, (10)
"lovely pool nearby. View of beautiful lagoon with manatee, Osprey and waterfowl."
SOUTH SEAS BAYSIDE Villa 5310

Newly listed, beautiful 2-bedroom, 2 bathroom condo in charming Boca Grande.

10.0 out of 10, Exceptional, (6)
"The condo looked brand new. Screened in back porch was amazing. Close walk to the sand bar. Really enjoyed our stay. "
Newly listed, beautiful 2-bedroom, 2 bathroom condo in charming Boca Grande.

Beachfront condo with pool, private balcony, and washer and dryer

10.0 out of 10, Exceptional, (1)
"Very nice condo in a great location."
Beachfront condo with pool, private balcony, and washer and dryer

Stunning Modern beach front unit - completely renovated! Includes golf cart!

9.8 out of 10, Exceptional, (101)
"Amazing location. Very clean and updated furnishings. Communication with the owner was great - very responsive. Highly recommend. "
The price is SAR 1,688
SAR 2,799 total
includes taxes & fees
19 May - 20 May
Stunning Modern beach front unit - completely renovated! Includes golf cart!

Little Gasparilla Island - Gulf view, golf cart, ferry, pool, boat dock, parking

9.8 out of 10, Exceptional, (80)
"The condo was in perfect condition! Owner is very nice, called day before check-in to see if we had any questions. We have stayed at different condos before and this one was top notch. Would definitely stay with them again."
Little Gasparilla Island - Gulf view, golf cart, ferry, pool, boat dock, parking

Bayfront 3 Bedroom Condo Walkable to Beach. Unit 1

9.8 out of 10, Exceptional, (42)
"This property is in a great location on beautiful Manasota Key. Communication was easy. Check in and checkout was easy as well. Definitely recommend!!"
The price is SAR 938
SAR 1,906 total
includes taxes & fees
27 Apr - 28 Apr
Bayfront 3 Bedroom Condo Walkable to Beach. Unit 1

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!
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

Other property types in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (843)
"The unit was clean and the workers were friendly!"
The price is SAR 848
SAR 950 total
includes taxes & fees
4 May - 5 May
The Suites at Fishermen’s Village- 2 Bedroom Suites

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 **

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (5)
"Chadwick Cove was recently renovated. The interior is cozy, clean and you have everything you need in the condo. Breakfast in the balcony to watch the sunrise at the bay was a plus."
The price is SAR 478
SAR 2,224 total
includes taxes & fees
28 Apr - 29 Apr
Chadwick Cove Resort & Marina
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.