Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Price was $1,692, price is now $1,394 per person
$1,394
per person
Mar 19 - Mar 23
found 11 hours ago
Roundtrip flight included
Hartford (BDL) 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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $4,053, price is now $2,898 per person
$2,898
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $3,160, price is now $2,445 per person
$2,445
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Key West (EYW)
Stay at this 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.
Oceans Edge Key West Resort, Hotel & Marina
Price was $2,469, price is now $1,949 per person
$1,949
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Perry Hotel & Marina Key West
Price was $2,394, price is now $1,902 per person
$1,902
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this 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.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $3,042, price is now $2,453 per person
$2,453
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Havana Cabana at Key West
New Town
Price was $2,260, price is now $1,845 per person
$1,845
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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
Price was $1,711, price is now $1,411 per person
$1,411
per person
Mar 19 - Mar 23
found 11 hours ago
Roundtrip flight included
Hartford (BDL) 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.
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.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $3,160, price is now $2,445 per person
$2,445
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Key West (EYW)
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 ...
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 ...
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. ...
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.
Fri, Jan 30 - Fri, Feb 6
TPA
Tampa Intl.
EYW
Key West Intl.
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Mon, Feb 9 - Fri, Feb 13
BOS
Logan Intl.
EYW
Key West Intl.
$195 Roundtrip, found 6 hours ago
$195
Roundtrip
found 6 hours ago
Tue, Sep 15 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$229 Roundtrip, found 5 days ago
$229
Roundtrip
found 5 days ago
Mon, Feb 16 - Thu, Feb 19
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$230 Roundtrip, found 6 days ago
$230
Roundtrip
found 6 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
- Key West Golf Club Vacations