Lower Keys Vacation Packages for 2026
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Lower Keys Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Amsterdam's Curry Mansion Inn
Key West Historic District
$1,372
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
There is no front desk, so checking in was a little confusing.
Beautiful building, remodeled rooms, comfortable bed, safe parking.
Reviewed on Sep 25, 2026
The Key West Hotel
Key West Historic District
$3,481
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
The Marker Key West Harbor Resort
Key West Historic District
$2,268
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Orchid Key Inn - Adults Only
Old Town Key West
$2,277
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Our stay was amazing. The breakfast and bar were wonderful to have. The staff was very accommodating and helpful. Our only issue was the cleanliness of the bathroom in the room There seemed to be like mildew around the bottom of the walls all around the bathroom. There was also a mildew smell in the room. They did clean the room every day, so I assume it was from flooding previously.
We will definately stay here again.
Reviewed on Sep 24, 2026
Hyatt Vacation Club at Beach House, Key West
$1,496
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), 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.
Excellent location. Balcony definitely had some nice views, pool was great. Friendly staff..
Reviewed on Sep 24, 2026
The Gardens Hotel
Old Town Key West
$2,321
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Top Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
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 ...
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Stay at this 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 reviews. ...
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Old Wooden Bridge Resort and Marina
1791 Bogie Drive Big Pine Key FL
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 ...
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
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 ...
Sunshine Key RV Resort & Marina
38801 Overseas Highway Big Pine Key FL
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, Jan 26 - Fri, Jan 29
TPA
Tampa Intl.
EYW
Key West Intl.
$154
Roundtrip
found 9 hours ago
Mon, Nov 16 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$339
Roundtrip
found 5 days ago
Sat, Nov 7 - Thu, Nov 12
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$359
Roundtrip
found 4 days ago
Mon, Feb 1 - Tue, Mar 2
ORD
O'Hare Intl.
EYW
Key West Intl.
$359
Roundtrip
found 6 days ago
Sun, Oct 18 - Thu, Oct 22
BOS
Logan Intl.
EYW
Key West Intl.
$427
Roundtrip
found 4 days ago
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All accommodation types in Lower Keys
More Types of Hotels
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