Beachside Vacation Packages for 2026
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.
Havana Cabana at Key West
New Town
Price was $1,493, price is now $1,136 per person
$1,136
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Bangor (BGR) 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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,510, price is now $2,337 per person
$2,337
per person
Apr 13 - Apr 18
just found
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $2,035, price is now $1,469 per person
$1,469
per person
Apr 13 - Apr 18
just found
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $2,474, price is now $1,834 per person
$1,834
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Bangor (BGR) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,091, price is now $1,583 per person
$1,583
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Bangor (BGR) 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
Price was $1,666, price is now $1,271 per person
$1,271
per person
Apr 13 - Apr 17
just found
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Top Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
1.81 km from Beachside
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
2.11 km from Beachside
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
5.23 km from Beachside
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
3.31 km from Beachside
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
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. ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
3.05 km from Beachside
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 ...
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
0.68 km from Beachside
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 ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
4.29 km from Beachside
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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
2.8 km from Beachside
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 ...
Pier House Resort & Spa
1 Duval St Key West FL
2.98 km from Beachside
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Hyatt Vacation Club at Beach House, Key West
5051 Overseas Highway Key West FL
3.61 km from Beachside
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. ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
3.41 km from Beachside
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. ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
2.77 km from Beachside
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 ...
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.
Sun, Feb 15 - Thu, Feb 19
TPA
Tampa Intl.
EYW
Key West Intl.
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Mon, Jul 27 - Tue, Aug 11
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Tue, Mar 24 - Sat, Apr 11
BOS
Logan Intl.
EYW
Key West Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Sat, Feb 21 - Wed, Feb 25
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$239 Roundtrip, found 4 days ago
$239
Roundtrip
found 4 days ago
Tue, Mar 10 - Tue, Mar 17
ORD
O'Hare Intl.
EYW
Key West Intl.
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago