Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Southwinds Motel
Old Town Key West
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Sundown Refuge by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Old Town Key West
per person
May 16 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located nearby.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
per person
May 27 - Jun 1
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Amelia Home by Avantstay In Historic Old Town w/ Pool
Old Town Key West
Save 100% on your flight
per person
May 27 - Jun 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
per person
May 22 - May 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. 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 Grand Guesthouse
Old Town Key West
Save 100% on your flight
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Southernmost Beach Resort
Old Town Key West
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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
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. ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
Havana Cabana at Key West - Adults Only
3420 N. Roosevelt Blvd, Key West, FL
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 ...
The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
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 ...
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
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, Jun 29 - Thu, Jul 3
TPA
Tampa Intl.
EYW
Key West Intl.
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Tue, Jun 3 - Wed, Jun 11
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Wed, May 7 - Wed, May 14
LGA
LaGuardia
EYW
Key West Intl.
$249 Roundtrip, found 2 hours ago
$249
Roundtrip
found 2 hours ago
Sat, May 31 - Wed, Jun 4
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$267 Roundtrip, found 1 day ago
$267
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Smathers Beach Vacations
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- Ernest Hemingway Home and Museum Vacations
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- Clarence S. Higgs Memorial Beach Park Vacations
- Key West Golf Club Vacations
- Stock Island Yacht Club & Marina Vacations