Our top choices for Gasparilla Island condo rentals
1. Chadwick Cove Resort & Marina
Chadwick Cove Resort & MarinaManasota Key
8.8 out of 10, Excellent, (31 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away.
Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
Niovys
$579 nightly
The price is $624
Nov 17 - Nov 18
Total with taxes and fees
2. Manasota Key Waterfront Condo Full Kitchen 1 Bed Boat Dock Beach Access Kayaks
Manasota Key Waterfront Condo Full Kitchen 1 Bed Boat Dock Beach Access KayaksManasota Key
$289 nightly
The price is $322
Nov 15 - Nov 16
Total with taxes and fees
3. Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!Matlacha
9.8 out of 10, Exceptional, (9 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
David H.
$152 nightly
The price is $168
Nov 17 - Nov 18
Total with taxes and fees
4. 1-Bedroom Condo with Waterview Patio Angel's Den - 1-Bedroom Condo with Waterview Patio Angel
1-Bedroom Condo with Waterview Patio Angel's Den - 1-Bedroom Condo with Waterview Patio AngelMatlacha
8.8 out of 10, Excellent, (3 reviews)
"Well kept for and very clean and comfortable ! Stayed one night on the way to North Captiva Island! We enjoyed everything about our stay!"
Kevin C.
$194 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
5. Waterfront Condo Walkable to Everything with Beach Access
Waterfront Condo Walkable to Everything with Beach AccessManasota Key
9.6 out of 10, Exceptional, (24 reviews)
"Nice place to stay "
Jon L.
$447 nightly
The price is $463
Dec 9 - Dec 10
Total with taxes and fees
6. Bayfront Condo, Prime Beach Access, Manasota Key
Bayfront Condo, Prime Beach Access, Manasota KeyManasota Key
9.4 out of 10, Exceptional, (24 reviews)
"Excellent place to stay! Would definitely stay again."
Justin B.
$339 nightly
The price is $376
Nov 27 - Nov 28
Total with taxes and fees
7. Knot Working Waterfront Cottage | Near Dearborn St | Pool | Dock | Beach
Knot Working Waterfront Cottage | Near Dearborn St | Pool | Dock | BeachOlde Englewood Village
$297 nightly
The price is $334
Nov 17 - Nov 18
Total with taxes and fees
8. Pirate's Paradise | Manasota Key Beach Condo | Dock & Pool
Pirate's Paradise | Manasota Key Beach Condo | Dock & PoolManasota Key
$330 nightly
The price is $367
Nov 15 - Nov 16
Total with taxes and fees
9. Captiva Villa 3115 | Upscale Residence | Great Amenities | Walk to the Beach
Captiva Villa 3115 | Upscale Residence | Great Amenities | Walk to the BeachCaptiva
7.2 out of 10, Good, (10 reviews)
"Great stay - everything was fantastic."
Tim S.
$389 nightly
The price is $432
Nov 15 - Nov 16
Total with taxes and fees
10. Bayfront Condo w/Private Beach on Manasota Key - Unit 311
Bayfront Condo w/Private Beach on Manasota Key - Unit 311Manasota Key
$483 nightly
The price is $501
Nov 15 - Nov 16
Total with taxes and fees
11. Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the BeachCaptiva
9.0 out of 10, Wonderful, (19 reviews)
"Great villa for 2 people. The place was clean, well stocked and comfortable. The pool was lovely. Check in / check out was seamless. Would definitely book again."
Connie A.
$488 nightly
The price is $542
Nov 14 - Nov 15
Total with taxes and fees
12. Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the BeachCaptiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
William B.
13. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the BeachCaptiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
Joseph S.
$500 nightly
The price is $556
Nov 14 - Nov 15
Total with taxes and fees
14. Beach Villa 2011-Stunning Beachfront Residence
Beach Villa 2011-Stunning Beachfront ResidenceCaptiva
9.6 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay. The villa met our expectations. We liked the beach access and the pool. "
Deb E.
$523 nightly
The price is $581
Nov 14 - Nov 15
Total with taxes and fees
15. Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private DeckManasota Key
$428 nightly
The price is $476
Nov 14 - Nov 15
Total with taxes and fees
16. Bayside Villa 5134 | Superb Residence | Free Bikes | Walk to the Beach
Bayside Villa 5134 | Superb Residence | Free Bikes | Walk to the BeachCaptiva
8.0 out of 10, Very good, (5 reviews)
"The condo is nice, private, and has a great view from the screen porch! "
Eric G.
17. Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
Beach Villa 2426 | Stunning Beachfront Residence on Captiva IslandCaptiva
9.6 out of 10, Exceptional, (26 reviews)
"There were a few minor issues, but for the most part, our stay was enjoyable. "
Ronald
$668 nightly
The price is $739
Nov 14 - Nov 15
Total with taxes and fees
18. Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)Manasota Key
$415 nightly
The price is $461
Dec 1 - Dec 2
Total with taxes and fees
19. Bayfront Condo with Private Beach - Unit 313
Bayfront Condo with Private Beach - Unit 313Manasota Key
$485 nightly
The price is $503
Nov 29 - Nov 30
Total with taxes and fees
20. Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the BeachCaptiva
7.8 out of 10, Good, (10 reviews)
"Property was perfect for an extended weekend getaway. Great location near a beautiful beach."
Janice S.
$408 nightly
The price is $454
Nov 14 - Nov 15
Total with taxes and fees
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.
Learn more about Gasparilla Island
Pristine beaches and the historic Port Boca Grande Lighthouse beckon visitors to this Gulf Coast gem. Rent a bike to explore charming Boca Grande, or cast a line for tarpon in the island's world-renowned fishing spots.
Photo by Dan Rose
Open Photo by Dan Rose