Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West
New Town
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Bishop Hotel Key West
Old Town Key West
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
3-4 Night Vacations in Beachside
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Beachside
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Beachside
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Save an average of 15% on thousands of hotels when you're signed in
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd, Key West, FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Nov 30 - Tue, Dec 9
TPA
Tampa Intl.
EYW
Key West Intl.
$77 Roundtrip, found 4 days ago
$77
Roundtrip
found 4 days ago
Tue, Aug 19 - Tue, Aug 26
ORD
O'Hare Intl.
EYW
Key West Intl.
$249 Roundtrip, found 4 days ago
$249
Roundtrip
found 4 days ago
Wed, Nov 12 - Wed, Nov 19
LGA
LaGuardia
EYW
Key West Intl.
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Tue, Oct 14 - Tue, Oct 21
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Discover Other Travel Deals
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