Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Key West / The Keys Collection
New Town
per person
May 24 - May 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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 the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Lavender Jungle by Avantstay Great Location w/ Patio & Shared Pool! Week Long Stays Only
Old Town Key West
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Old Town Key West
per person
May 24 - May 28
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 Ernest Hemingway Home and Museum are located nearby.
Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only
Old Town Key West
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Old Town Key West
per person
Jun 5 - Jun 9
found 7 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this 3.5-star cottage in Key West. Enjoy free parking, concierge services, and premium TV channels. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
per person
May 24 - May 28
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 balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach are located nearby.
DoubleTree Resort by Hilton Grand Key - Key West
per person
May 24 - May 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pier House Resort & Spa
Key West Historic District
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 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.
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 ...
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. ...
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 ...
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.
Thu, Jun 26 - Fri, Jul 4
TPA
Tampa Intl.
EYW
Key West Intl.
$77 Roundtrip, found 15 hours ago
$77
Roundtrip
found 15 hours 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 5 days ago
$249
Roundtrip
found 5 days ago
Mon, May 12 - Tue, Aug 12
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$253 Roundtrip, found 6 hours ago
$253
Roundtrip
found 6 hours ago
Discover Other Travel Deals
- Smathers Beach Vacations
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- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Key West Golf Club Vacations
- Stock Island Yacht Club & Marina Vacations