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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)
"This was an excellent property to stay in. I will definitely rebook when I travel to Englewood, Fl. "
The price is AED 551
AED 2,269 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, (137)
"This condo was just perfect for a quiet, relaxing beach vacation. It was very nicely furnished, extremely comfortable and obviously well maintained. We loved the proximity to both the beach and the pool. All in all, we were delighted with everything about this wonderful place."
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)
"Love stay at this right on the beach condo"
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)
"Property was very small but perfect for just the two of us. It really is right on the beach, and worth every penny!"
Sand in Your Toes . . . Right Out Your Front Door!

Chillax on the Beach or by the Bay!

9.8 out of 10, Exceptional, (14)
"Very nice place"
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)
"Love the place. We’ll be back. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

The Summer Wind @ Manasota Key

10.0 out of 10, Exceptional, (9)
"Great location, nice beach, clean and updated unit."
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 quiet complex. The condo was perfect for 2 and bigger than we expected. "
Remodeled Manasota Key Bay Side 1 Bedroom Condo

South seas beach villa 2428

9.6 out of 10, Exceptional, (27)
"Great management. Great communication. Would stay again anytime. "
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)
"From the outside it does not look like much, just some apartments. But when we opened the door and stepped in. It was nice, It felt like Florida, it was bright and cozy and super clean. Not 1 hair to be found. (My petp"
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)
"Loved our stay! Was clean, close to town, and right on the beach with two pools for kids to choose from. We would love to book again sometime."
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)
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)
"We had a great visit. The house had everything we needed and the location is fantastic!"
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)
"We really enjoyed our time in Florida. Property was clean and well located close to beach. Property owner was also very nice and answered all our questions. Would definitely go back 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 was comfortable for 7 adults. Communication with property manager was easy and helpful/ great central location. "
The price is AED 918
AED 1,866 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)
"We had a great week! It was our first time to Manasota Key and we plan to return!"
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.
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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, (840)
"Very nice place to stay"
The price is AED 830
AED 930 total
includes taxes & fees
30 Apr - 1 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)
"Everything was perfect."
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)
"This was an excellent property to stay in. I will definitely rebook when I travel to Englewood, Fl. "
The price is AED 551
AED 2,269 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.

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