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Featured Condo Rentals in Gasparilla Island

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (2)
"Very friendly service!! Jim was amazing ! "
The price is AU$575
includes taxes & fees
15 Mar - 16 Mar
Chadwick Cove Resort & Marina

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!

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

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

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!

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!

9.8 out of 10, Exceptional, (48)
"Extremely clean property, as advertisized, very safe, excellent beach access and property manager very efficient and helpful. Could use a new patio table as current one is quite cracked."
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

Stunning Harborview Villa in South Seas

9.0 out of 10, Wonderful, (24)
"Captiva is not what she used to be yet. Not many open businesses in Captiva. Very few people at the condos The condo was beautiful! We enjoyed the short walk to the beach. The hot tub only worked one of the days. We did hear construction noise throughout our stay. It starts around 7/8 am. "
Stunning Harborview Villa in South Seas

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

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

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!

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.

10.0 out of 10, Exceptional, (73)
"This property was the perfect beachfront location for our vacation. It has everything you need to set up housekeeping, with a spacious gulf side balcony upon which to relax between beach walks. The owner provided complete information so that arrival and leaving were easy."
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

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

10.0 out of 10, Exceptional, (90)
"Very clean and well equipped. Location was perfect for my wife and I. Would stay here again "
Manasota Key Condo! Private Beach access.Gulf and Bay views

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

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

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

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

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.
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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, (798)
"We stayed in the grand harbor sunset suite and it was beautiful!! The space was very clean and the view off the balcony was wonderful! Great restaurant choices right there and we loved the entire atmosphere. We will definitely be back!"
The price is AU$421
includes taxes & fees
1 Apr - 2 Apr
The Suites at Fishermen’s Village- 2 Bedroom Suites

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (2)
"Very friendly service!! Jim was amazing ! "
The price is AU$575
includes taxes & fees
15 Mar - 16 Mar
Chadwick Cove Resort & Marina

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.