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 $1,145, price is now $740 per person
$740
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,854, price is now $1,090 per person
$1,090
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Stay at this 3.5-star 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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,046, price is now $1,805 per person
$1,805
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,960, price is now $1,194 per person
$1,194
per person
Jan 21 - Jan 25
found 18 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Key West (EYW)
Stay at this 4-star 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.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,581, price is now $1,020 per person
$1,020
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,365, price is now $947 per person
$947
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Top Hotel Deals
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
3.31 km from Beachside
Stay at this 4-star 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
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. ...
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 ...
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 ...
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 ...
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
Stay at this 4-star business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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. ...
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 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 ...
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 ...
The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
4.29 km from Beachside
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 ...
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 - Thu, Jan 22
TPA
Tampa Intl.
EYW
Key West Intl.
$239 Roundtrip, found 5 days ago
$239
Roundtrip
found 5 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$250 Roundtrip, found 2 days ago
$250
Roundtrip
found 2 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$253 Roundtrip, found 2 days ago
$253
Roundtrip
found 2 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago