Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $1,293, price is now $905 per person
$905
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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. Popular attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,636, price is now $1,633 per person
$1,633
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,973, price is now $1,323 per person
$1,323
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this 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 and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,795, price is now $1,252 per person
$1,252
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,466, price is now $1,065 per person
$1,065
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 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.
Havana Cabana at Key West
New Town
Save 100% on your flight
Price was $1,563, price is now $1,167 per person
$1,167
per person
Mar 20 - Mar 24
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 free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $2,572, price is now $1,937 per person
$1,937
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,800, price is now $1,363 per person
$1,363
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms 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
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this 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
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this 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
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise 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.
Sat, Feb 7 - Mon, Feb 9
TPA
Tampa Intl.
EYW
Key West Intl.
$134 Roundtrip, found 17 hours ago
$134
Roundtrip
found 17 hours ago
Mon, Mar 30 - Wed, Apr 8
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$211 Roundtrip, found 7 hours ago
$211
Roundtrip
found 7 hours ago
Thu, Apr 16 - Mon, Apr 20
LGA
LaGuardia
EYW
Key West Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Tue, Sep 15 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Discover Other Travel Deals
- Smathers Beach Vacations
- Duval Street Vacations
- Mallory Square Vacations
- Southernmost Point Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Stock Island Yacht Club & Marina Vacations
- Key West Butterfly and Nature Conservatory Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Florida Keys National Marine Sanctuary Vacations