Beachside Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $835, price is now $536 per person
$536
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Havana Cabana at Key West
New Town
Save 100% on your flight
Price was $1,004, price is now $690 per person
$690
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Douglas House
Old Town Key West
Save 100% on your flight
Price was $1,388, price is now $973 per person
$973
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Reach Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $1,483, price is now $1,043 per person
$1,043
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
Price was $1,208, price is now $853 per person
$853
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 4-star guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Top Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
3.41 km from Beachside
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. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
5.25 km from Beachside
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 ...
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
0.68 km from Beachside
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 ...
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
2.8 km from Beachside
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
3.34 km from Beachside
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 ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
1.85 km from Beachside
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. ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
3.31 km from Beachside
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
1.24 km from Beachside
Stay at this 3-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Pier House Resort & Spa
1 Duval St, Key West, FL
2.98 km from Beachside
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. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
1.23 km from Beachside
Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Hyatt Vacation Club at Beach House, Key West
5051 Overseas Highway, Key West, FL
3.61 km from Beachside
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd, Key West, FL
1.76 km from Beachside
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. ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard, Key West, FL
2.77 km from Beachside
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. 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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Sep 17 - Tue, Sep 23
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Wed, Sep 17 - Wed, Sep 24
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Sun, Jan 11 - Wed, Jan 21
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Thu, Oct 30 - Fri, Nov 14
PHL
Philadelphia Intl.
EYW
Key West Intl.
$363 Roundtrip, found 3 days ago
$363
Roundtrip
found 3 days ago
Sun, Nov 16 - Sun, Nov 23
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago