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.
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachside
$1,538
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) 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.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight
$1,604
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) 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.
Great hotel to stay 👌

Reviewed on Aug 26, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
$2,454
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip flight included
Islip (ISP) 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

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Old Town Key West
$1,805
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Southernmost Point are located nearby.
We loved the location (right off Duvall)! It was tucked back a little walkway that led to a deck with an umbrella table, outdoor cushioned couches, and a hot tub. Nice and private! We could occasionally hear a neighbor talking, but honestly we felt like we were completely alone. The condo is tiny, but perfect for a couple. Kitchen is stocked nicely, lots of extra towels & linens, plus beach towels. The a/c in the main room had a little trouble keeping up with the soaring temps (feels like 104° during our visit) so the window unit in the bedroom was a nice feature. We had a golf cart one day and there is a perfect sized parking spot right in front of the condo. There's hooks on the fence to secure bikes too. The communication was excellent; we received text messages and emails regularly and honestly, I loved the text messages throughout our stay just touching base. It's a nice extra touch. We would come back in a heartbeat!

Reviewed on Aug 12, 2026

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Old Town Key West
$1,623
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The location to the things we wanted to do was perfect

Reviewed on May 1, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,907
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip flight included
Islip (ISP) 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 staff were very pleasant and helpful and the hotel was very clean. We felt it is located well for us to get around to things we wanted to go to. Really the only minor complaint would be that the pool water was actually too warm. Not a deal breaker by any means. All in all we had a great experience and will gladly go back.

Reviewed on Aug 24, 2026

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Top Hotel Deals

Parmer's Resort

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

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. ...
Old Wooden Bridge Resort and Marina

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

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 ...
Sugar Loaf Lodge

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 ...
Looe Key Reef Resort

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. ...
Sunshine Key RV Resort & Marina

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.
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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.

Delta
Wed, Sep 30 - Wed, Oct 7
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Key West Intl., returning Wed, Oct 7, priced at $259 found 1 day ago
American Airlines
JetBlue Airways
United