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Key West Vacation Packages

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A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West
Florida
United States of America
North America
Hotwire.com

Key West Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Paradise Inn Key West - Adults Only

3.5 out of 5

Save 100% on your flight

Price was $1,637, price is now $1,111 per person

$1,111

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Key West (EYW)

Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Very cute and clean property. The only thing I didn’t like was the fee for parking our rented golf cart in property.

Reviewed on Sep 30, 2026

The Key West Hotel

3 out of 5

Save 100% on your flight

Price was $4,226, price is now $2,657 per person

$2,657

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Orchid Key Inn - Adults Only

3.5 out of 5

Save 100% on your flight

Price was $2,282, price is now $1,553 per person

$1,553

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

This was my favorite getaway yet! It will be my go to on any return trip to the Keys. The staff has been exceptional, the location perfect, and the hotel over exceeded everything I read about it. Quiet rooms, everything we needed, great bedding and very comfortable. Lovely continental breakfast is above and beyond. Will definitely be back!

Reviewed on Sep 27, 2026

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5

Save 100% on your flight

Price was $2,427, price is now $1,726 per person

$1,726

per person

Nov 16 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

We would definitely stay again, it was a beautiful resort..

Reviewed on Sep 30, 2026

The Gardens Hotel

4 out of 5

Save 100% on your flight

Price was $2,517, price is now $1,806 per person

$1,806

per person

Nov 16 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5

Save 100% on your flight

Price was $1,868, price is now $1,346 per person

$1,346

per person

Nov 16 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Fantastic

Reviewed on Sep 30, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5

Save 100% on your flight

Price was $3,483, price is now $2,581 per person

$2,581

per person

Nov 18 - Nov 23

found 12 hours ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Loved it

Reviewed on Mar 20, 2026

Southernmost Beach Resort and Guesthouses

4 out of 5

Save 100% on your flight

Price was $2,287, price is now $1,695 per person

$1,695

per person

Nov 16 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.

We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.

Reviewed on Oct 1, 2026