Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
per person
Aug 11 - Aug 15
found 14 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip 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.
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Orchid Key Inn - Adults Only
Old Town Key West
per person
Aug 11 - Aug 15
found 14 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Southernmost Beach Resort and Guesthouses
Old Town Key West
per person
Aug 11 - Aug 15
found 14 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star eco-certified apartment in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Casa Grande by Avantstay Dt Key West Near South Beach w/ Pool
Old Town Key West
Save 100% on your flight
per person
Aug 4 - Aug 9
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, private pools, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West
per person
Aug 11 - Aug 15
found 14 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
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. ...
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 ...
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. ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd, Key West, FL
Enjoy free WiFi, free parking, and breakfast (surcharge).
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Stay at this 3-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
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.
Wed, Dec 3 - Sun, Dec 7
TPA
Tampa Intl.
EYW
Key West Intl.
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Wed, Nov 12 - Wed, Nov 19
LGA
LaGuardia
EYW
Key West Intl.
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Wed, Oct 8 - Sat, Oct 18
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Tue, Aug 5 - Tue, Aug 12
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$253 Roundtrip, found 18 hours ago
$253
Roundtrip
found 18 hours ago
Discover Other Travel Deals
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- Key West Golf Club Vacations
- Stock Island Yacht Club & Marina Vacations
- Clarence S. Higgs Memorial Beach Park Vacations