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 - Adults Only
New Town
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
per person
May 22 - May 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Easy Livin' by Avantstay Key West Home w/ Pool & BBQ Week Long Stays Only
Old Town Key West
Save 100% on your flight
per person
May 3 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, concierge services, and balconies. Popular attractions Duval Street and Mallory Square are located nearby.
The Perry Hotel & Marina Key West
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Grand Guesthouse
Old Town Key West
Save 100% on your flight
per person
May 11 - May 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Key West Charming by Avantstay Communal Pool Gated Community Near Fort Zachary Taylor Park Week Long Stays
Old Town Key West
Save 100% on your flight
per person
May 17 - May 24
found 14 hours ago
Roundtrip non-stop flight included
Washington (DCA) 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.
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
per person
May 3 - May 10
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.
Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Old Town Key West
Save 100% on your flight
per person
May 3 - May 10
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 free parking, balconies, and in-room washers/dryers. 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
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
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 ...
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 ...
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 ...
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 ...
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, Jul 16 - Mon, Jul 21
TPA
Tampa Intl.
EYW
Key West Intl.
$162 Roundtrip, found 4 days ago
$162
Roundtrip
found 4 days ago
Tue, May 6 - Tue, May 13
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$199 Roundtrip, found 23 hours ago
$199
Roundtrip
found 23 hours ago
Mon, Apr 28 - Thu, May 1
LGA
LaGuardia
EYW
Key West Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Wed, May 14 - Tue, May 20
ORD
O'Hare Intl.
EYW
Key West Intl.
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago
Discover Other Travel Deals
- Smathers Beach Vacations
- Duval Street Vacations
- Mallory Square Vacations
- Southernmost Point Vacations
- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Key West Golf Club Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Stock Island Yacht Club & Marina Vacations