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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $2,611, price is now $1,608 per person
$1,608
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $4,972, price is now $2,810 per person
$2,810
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $5,124, price is now $3,003 per person
$3,003
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $2,678, price is now $1,645 per person
$1,645
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Perry Hotel & Marina Key West
Save 100% on your flight
Price was $3,506, price is now $2,341 per person
$2,341
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $3,948, price is now $2,685 per person
$2,685
per person
Feb 1 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. 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
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. ...
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 ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
1.85 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 ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
5.25 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 ...
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 helpful staff 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 ...
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 ...
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 ...
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 ...
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 ...
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd Key West FL
1.24 km from Beachside
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
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 ...
La Concha Key West, Autograph Collection
430 Duval St Key West FL
2.54 km from Beachside
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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.
Sat, Jan 17 - Wed, Jan 21
TPA
Tampa Intl.
EYW
Key West Intl.
$230 Roundtrip, found 6 days ago
$230
Roundtrip
found 6 days ago
Wed, Apr 1 - Tue, Apr 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
Wed, Mar 4 - Tue, Mar 10
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Wed, Apr 1 - Tue, Apr 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$319 Roundtrip, found 5 days ago
$319
Roundtrip
found 5 days ago
Mon, Feb 23 - Wed, Mar 11
ORD
O'Hare Intl.
EYW
Key West Intl.
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago