Keewaydin Island Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Keewaydin Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $636, price is now $349 per person
$349
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Calusa Nature Center and Planetarium and Topgolf are located nearby.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $714, price is now $356 per person
$356
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,192, price is now $1,174 per person
$1,174
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4.5-star luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,549, price is now $971 per person
$971
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Edison Beach House
Save 100% on your flight
Price was $1,352, price is now $863 per person
$863
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $784, price is now $511 per person
$511
per person
Sep 28 - Oct 5
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
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Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
15.81 km from city center
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S, Naples, FL
7.62 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South, Naples, FL
7.87 km from city center
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd, Marco Island, FL
17.55 km from city center
Stay at this 4-star beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Hilton Naples
5111 Tamiami Trl N, Naples, FL
15.55 km from city center
Stay at this 4-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Ritz-Carlton, Naples
280 Vanderbilt Beach Rd, Naples, FL
20.48 km from city center
Stay at this 5-star luxury resort in Naples. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Popular attractions Vanderbilt Beach and Barefoot ...
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N, Naples, FL
15.06 km from city center
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Marco Beach Ocean Suites
480 S Collier Blvd, Marco Island, FL
17.15 km from city center
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Fairways Inn of Naples
103 Palm River Blvd, Naples, FL
22.56 km from city center
Stay at this 3-star hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Bayfront Inn Fifth Avenue
1221 5th Ave S, Naples, FL
8.1 km from city center
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the bar in our reviews. ...
JW Marriott Marco Island Beach Resort
400 S Collier Blvd, Marco Island, FL
16.83 km from city center
Stay at this 4-star beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
Trianon Bonita Bay
3401 Bay Commons Dr, Bonita Springs, FL
31.09 km from city center
Stay at this 3.5-star family-friendly hotel in Bonita Springs. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool ...
Inn on Fifth
699 5th Ave S, Naples, FL
7.99 km from city center
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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See all available properties in Keewaydin Island
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Feb 21 - Sat, Feb 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$106 Roundtrip, found 17 hours ago
$106
Roundtrip
found 17 hours ago
Fri, Sep 12 - Tue, Sep 16
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Sun, Oct 19 - Fri, Oct 24
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Tue, Oct 7 - Tue, Oct 14
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Tue, Dec 2 - Tue, Dec 9
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago