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.
The Marker Key West Harbor Resort
Key West Historic District
Price was $1,567, price is now $1,114 per person
$1,114
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) 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.
The Key West Hotel
Key West Historic District
Price was $2,356, price is now $1,528 per person
$1,528
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) 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.
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!
Reviewed on Oct 29, 2026
The Gardens Hotel
Old Town Key West
Price was $2,404, price is now $1,748 per person
$1,748
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) 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.
Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West
Reviewed on Nov 8, 2026
Southernmost House - Adult Exclusive
Old Town Key West
Price was $2,081, price is now $1,539 per person
$1,539
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Stunning, I dont have to say anymore
Reviewed on Nov 10, 2026
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Beachside
Price was $2,491, price is now $1,922 per person
$1,922
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy free parking, a beach locale, and balconies. Popular attractions Duval Street and Smathers Beach are located nearby.
Orchid Key Inn - Adults Only
Old Town Key West
Price was $1,463, price is now $1,131 per person
$1,131
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) 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 Mallory Square are located nearby.
We LOVED our stay here. Small, boutique motel with a vintage feel. Right on Duvall, but you would never know it once in the motel. It was secluded and quiet with a lovely tropical feel. Loved the grounds - beautiful flowers, palms, gorgeous pool at night with candles around the tables. The staff was so helpful and friendly. Breakfast buffet is pretty good, but the areas around the pool were my favorite to sit & relax with a glass of wine from the bar. Our room was clean & comfortable. Lots of little amenities. Coffee cart in the a.m., flavored water all day by the pool. Bike rentals right there if you want them. The two women that worked the front desk all week were so great. Sorry to leave & can’t wait to return!
Reviewed on Nov 8, 2026
Top Hotel Deals
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 ...
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
3.36 km from city center
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. ...
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 a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 Bahia ...
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
3.96 km from city center
Stay at this vacation home in Summerland Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
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.
Wed, Feb 3 - Wed, Feb 10
TPA
Tampa Intl.
EYW
Key West Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Wed, Feb 3 - Wed, Feb 10
TPA
Tampa Intl.
EYW
Key West Intl.
$261 Roundtrip, found 4 days ago
$261
Roundtrip
found 4 days ago
Tue, Dec 1 - Mon, Dec 21
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$335 Roundtrip, found 5 days ago
$335
Roundtrip
found 5 days ago
Fri, Mar 5 - Wed, Mar 10
DTW
Detroit Metropolitan Wayne County
EYW
Key West Intl.
$386 Roundtrip, found 2 days ago
$386
Roundtrip
found 2 days ago
Wed, Feb 3 - Sun, Feb 14
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago