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Our top choices for Gasparilla Island condo rentals

Interior
2/2 Spacious Unit

Condo in Port Charlotte

2/2 Spacious Unit
9.2 out of 10, Wonderful, (10)
"Great location close to everything.beautiful place well stocked nice host."
United States
Elisabeth B.
$256 nightly
The price is $283
Dec 26 - Dec 27
Total with taxes and fees
2/2 Spacious Unit
Property grounds
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$573 nightly
The price is $618
Jan 12 - Jan 13, 2026
Total with taxes and fees
Chadwick Cove Resort & Marina
Private kitchen
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Condo in Matlacha

2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
9.8 out of 10, Exceptional, (8)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
$155 nightly
The price is $171
Jan 4 - Jan 5, 2026
Total with taxes and fees
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Smart TV
Boca Sunny Side Condo in Florida

Condo in Rotonda West

Boca Sunny Side Condo in Florida
2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent "
United Kingdom
Peter S.
$358 nightly
The price is $396
Jan 4 - Jan 5, 2026
Total with taxes and fees
Boca Sunny Side Condo in Florida
Terrace/patio
6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel

Condo in Matlacha

6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel
10.0 out of 10, Exceptional, (2)
"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.
$195 nightly
The price is $215
Dec 28 - Dec 29
Total with taxes and fees
6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel
Property grounds
6 Person 1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!

Condo in Burnt Store

6 Person 1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!
$199 nightly
The price is $219
Dec 26 - Dec 27
Total with taxes and fees
6 Person 1-Bedroom Condo with Waterview Patio Starfish - Welcome to our newly renovated one-bedroom condo!
TV
Chic Captiva Villa Residence with Great Amenities

Condo in Captiva

Chic Captiva Villa Residence with Great Amenities
9.0 out of 10, Wonderful, (11)
"Nice property well equiped short walk to the beautiful beach/ picturesque little town. Very pleased. "
United States
Carlos
$465 nightly
The price is $512
Dec 26 - Dec 27
Total with taxes and fees
Chic Captiva Villa Residence with Great Amenities
Property grounds
Modern Captiva Villa Residence with Great Amenities

Condo in Captiva

Modern Captiva Villa Residence with Great Amenities
7.8 out of 10, Good, (10)
"Property was perfect for an extended weekend getaway. Great location near a beautiful beach."
United States
Janice S.
$399 nightly
The price is $442
Jan 17 - Jan 18, 2026
Total with taxes and fees
Modern Captiva Villa Residence with Great Amenities
Dining
Your Perfect Vacation Getaway . Brand-New Sleek and Stylish Modern Home,

Condo in Port Charlotte

Your Perfect Vacation Getaway . Brand-New Sleek and Stylish Modern Home,
10.0 out of 10, Exceptional, (2)
"Everything about this place was great! Would recommend it to anyone who stays in this area. Thank you for everything. "
United States
Kari G.
$243 nightly
The price is $268
Dec 27 - Dec 28
Total with taxes and fees
Your Perfect Vacation Getaway . Brand-New Sleek and Stylish Modern Home,
Property grounds
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

Condo in Manasota Key

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
9.8 out of 10, Exceptional, (39)
"Perfect for 2 adults and 2 kids. The house was very clean and all the extras in the kitchen were nice. Also, beach essentials are onsite so no need to bring much. Found lots of sharks teeth too! "
United States
Koren L.
$321 nightly
The price is $357
Jan 14 - Jan 15, 2026
Total with taxes and fees
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
TV, offices
Gorgeous Newly Renovated Marina View Condo

Condo in Captiva

Gorgeous Newly Renovated Marina View Condo
9.4 out of 10, Exceptional, (3)
"Our family of 3 (our babe is almost 2) enjoyed four nights at this condo. We enjoyed the easy access to our boat (booked through South Seas Marina) and the view from the condo was fantastic. The pool was conveniently located next to our building and we grilled out every night. 10/10 experience. We’ll definitely be back to book this very condo! "
United States
Jennifer C.
Gorgeous Newly Renovated Marina View Condo
TV, offices
Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6

Condo in Captiva

Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6
9.4 out of 10, Exceptional, (13)
"Condo was clean, comfortable and in a great location. We walked to restaurants, beach and pool. Very relaxing!"
United States
Lindsay B.
$510 nightly
The price is $562
Dec 24 - Dec 25
Total with taxes and fees
Stunning Bayside Villa w/ Enclosed Lanai, Sleeps 6
Private kitchen
Enjoyable 2-bedroom/ 2 Bathroom condo with AC in North Port

Condo in Warm Mineral Springs

Enjoyable 2-bedroom/ 2 Bathroom condo with AC in North Port
2.0 star property
$348 nightly
The price is $388
Dec 24 - Dec 25
Total with taxes and fees
Enjoyable 2-bedroom/ 2 Bathroom condo with AC in North Port
Dining
Tranquil 2 BR/ 2 BA condo in Rotonda West with screened lanai, and canal

Condo in Pebble Beach

Tranquil 2 BR/ 2 BA condo in Rotonda West with screened lanai, and canal
$396 nightly
The price is $438
Dec 26 - Dec 27
Total with taxes and fees
Tranquil 2 BR/ 2 BA condo in Rotonda West with screened lanai, and canal
On the beach, sun loungers, beach towels
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Condo in Manasota Key

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
9.4 out of 10, Exceptional, (66)
"We had an amazing stay! The pictures of the condo do not do it justice. The condo was clean and comfortable. There was plenty of space to keep everyone happy. The only downfall ( and not one that would keep us from returning ) is the parking. We drive a Tahoe and were unable to fit it in the assigned parking spot due to the pillars and actual property size. However they have a solution as there is an overflow lot they allow you to park in that is walkable! Don’t let this detour you as the condo...
United States
JENNA
$449 nightly
The price is $497
Dec 24 - Dec 25
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Beach
Stunning Harborview Residence on Captiva Island

Condo in Captiva

Stunning Harborview Residence on Captiva Island
9.0 out of 10, Wonderful, (26)
"Nice accommodations! "
United States
Kimberly H.
$528 nightly
The price is $582
Dec 24 - Dec 25
Total with taxes and fees
Stunning Harborview Residence on Captiva Island
Exterior
Chic Marina View Residence on Captiva Island

Condo in Captiva

Chic Marina View Residence on Captiva Island
8.6 out of 10, Excellent, (17)
"Place was as advertised. Exceeded expectations!!!"
United States
Russell G.
$545 nightly
The price is $601
Dec 24 - Dec 25
Total with taxes and fees
Chic Marina View Residence on Captiva Island
Dining
Blue Crab Key Condo! Two Bedroom Two Bathroom!

Condo in Bokeelia

Blue Crab Key Condo! Two Bedroom Two Bathroom!
$503 nightly
The price is $555
Dec 24 - Dec 25
Total with taxes and fees
Blue Crab Key Condo! Two Bedroom Two Bathroom!
Private kitchen
8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!

Condo in Matlacha

8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
$300 nightly
The price is $332
Jan 2 - Jan 3, 2026
Total with taxes and fees
8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
Beach nearby
Turtle Bay 1A – Island Escape on Manasota Key

Condo in Manasota Key

Turtle Bay 1A – Island Escape on Manasota Key
9.8 out of 10, Exceptional, (16)
"We really enjoyed our stay! Great location!"
United States
Kate K.
$399 nightly
The price is $441
Dec 29 - Dec 30
Total with taxes and fees
Turtle Bay 1A – Island Escape on Manasota Key
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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Top Gasparilla Island Hotel Reviews

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

10/10 Excellent
"Great place"
Matthew 7-night trip
Posted 2 days ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Gasparilla Island

Gasparilla Island Condo Rentals information

Number of reviews
236
Accommodation
134 Condo Rentals
Lowest Price
$171
Highest Price
$618

Frequently asked questions

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