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Keewaydin Island Vacation Packages

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A coastal landscape with a sandy beach, clear turquoise waters, and a network of small islands.

Keewaydin Island
Naples
Florida
United States of America
North America
Hotwire.com

Keewaydin Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5

Save 100% on your flight

Price was $539, price is now $336 per person

$336

per person

Sep 17 - Sep 21

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Fort Myers (RSW)

Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Fishermen's Village and Peace River are located nearby.

The Perry Hotel Naples

4.5 out of 5

Save 100% on your flight

Price was $1,123, price is now $625 per person

$625

per person

Oct 19 - Oct 24

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Fort Myers (RSW)

Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.

Tween Waters Island Resort & Spa

3 out of 5

Save 100% on your flight

Price was $1,707, price is now $1,018 per person

$1,018

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.

Very nice place to enjoy and have a good time. Beach across the street, pool bar and restaurants nearby. Super quite and relaxing. We definitely recommend this place and hopefully coming back soon

Reviewed on Aug 10, 2026

Casa Ybel Resort

2.5 out of 5

Save 100% on your flight

Price was $1,542, price is now $958 per person

$958

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Sanibel Island Lighthouse are located nearby.

South Seas

3.5 out of 5

Save 100% on your flight

Price was $1,576, price is now $984 per person

$984

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this beach resort in Captiva. Enjoy 6 outdoor pools, 5 restaurants, and a private beach. Popular attractions Bowman's Beach and Jungle Drums are located nearby.

Casa Tiki

3 out of 5

Save 100% on your flight

Price was $1,055, price is now $677 per person

$677

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Stay at this vacation home in Cape Coral. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Four Mile Cove Ecological Preserve and Coralwood Mall are located nearby.

Wiggins Pass Chalet

4 out of 5

Save 100% on your flight

Price was $659, price is now $460 per person

$460

per person

Oct 19 - Oct 24

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Fort Myers (RSW)

Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.

Amazing stay! Great customer service, I forgot the front desks name but she was exceptional! Very clean and big rooms! Would definitely stay again!

Reviewed on Aug 10, 2026

Windward Passage Resort

2 out of 5

Save 100% on your flight

Price was $630, price is now $447 per person

$447

per person

Sep 17 - Sep 21

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Fort Myers (RSW)

Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.

Great location, very clean

Reviewed on Aug 6, 2026