Lower Keys Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Lower Keys Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,546, price is now $1,023 per person
$1,023
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $2,566, price is now $1,426 per person
$1,426
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,597, price is now $1,461 per person
$1,461
per person
Dec 22 - Dec 27
found 1 hour ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,799, price is now $1,057 per person
$1,057
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,420, price is now $2,085 per person
$2,085
per person
Dec 22 - Dec 27
found 1 hour ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,086, price is now $1,369 per person
$1,369
per person
Dec 22 - Dec 27
found 1 hour ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Top Hotel Deals
Old Wooden Bridge Resort and Marina
1791 Bogie Drive, Big Pine Key, FL
14.91 km from city center
Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Blue ...
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
10.76 km from city center
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
8.16 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
3.36 km from city center
Stay at this 3-star hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our ...
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
9.13 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
Sunshine Key RV Resort & Marina
38801 Overseas Highway, Big Pine Key, FL
25.09 km from city center
Enjoy a private beach, a marina, and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.
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.
Tue, Dec 9 - Wed, Dec 17
BOS
Logan Intl.
EYW
Key West Intl.
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Sat, Dec 13 - Thu, Dec 18
BOS
Logan Intl.
EYW
Key West Intl.
$238 Roundtrip, found 22 hours ago
$238
Roundtrip
found 22 hours ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$296 Roundtrip, found 4 days ago
$296
Roundtrip
found 4 days ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
EYW
Key West Intl.
$311 Roundtrip, found 4 days ago
$311
Roundtrip
found 4 days ago