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Key West Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Winslow's Bungalows - Key West Historic Inns
Price was $1,283, price is now $891 per person
$891
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Two concerns:
1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result.
2) concern may be equal parts
Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.
Reviewed on Sep 1, 2026

The Key West Hotel
Save 100% on your flight
Price was $3,492, price is now $2,234 per person
$2,234
per person
Oct 2 - Oct 9
found 1 day 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.
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026

Kona Kai Oasis
Price was $2,028, price is now $1,400 per person
$1,400
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.

The Gardens Hotel
Save 100% on your flight
Price was $1,998, price is now $1,419 per person
$1,419
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
I honestly can’t rave enough about this place. From the first phone call to check out, everyone was so pleasant and helpful. The grounds are immaculately maintained, the property is absolutely beautiful. Tastefully whimsical !!!
The rooms are clean, the beds are comfy, all the way down to the linens. Everything is spot on. The location is just off Duval Street but you would never know it. It is so charming. Our waitress/bartender was the best! We met the owner and all I can say is she is the most delightful woman. You can see she has her heart in the establishment. There is even a wine gallery on site. I can’t wait to come back!
Reviewed on Sep 2, 2026

Ridley House - Key West Historic Inns
Price was $1,597, price is now $1,134 per person
$1,134
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Stayed here for a birthday celebration and it was perfect. Breakfast by the pool every morning, rooms were big, and we didn't hear anything throughout our stay so we slept well!
Reviewed on Sep 2, 2026

The Perry Hotel & Marina Key West
Price was $1,752, price is now $1,256 per person
$1,256
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this 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.

Amelia Home by Avantstay In Historic Old Town w/ Pool
Save 100% on your flight
Price was $3,997, price is now $2,882 per person
$2,882
per person
Nov 18 - Nov 24
found 1 day ago
Roundtrip flight included
Fargo (FAR) 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

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,753, price is now $1,272 per person
$1,272
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
This was my first time at an Hyatt and it was great.. loved the stay all around. No complaints about anything. Looking forward to next time.
Reviewed on Aug 31, 2026
Key West Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Key West Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Sep 14 - Thu, Sep 17
TPA
Tampa Intl.
EYW
Key West Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found

Tue, Oct 27 - Thu, Nov 12
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$324 Roundtrip, found 3 hours ago
$324
Roundtrip
found 3 hours ago

Wed, Oct 7 - Wed, Oct 14
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$328 Roundtrip, found 4 hours ago
$328
Roundtrip
found 4 hours ago

Tue, Feb 2 - Wed, Feb 10
DTW
Detroit Metropolitan Wayne County
EYW
Key West Intl.
$333 Roundtrip, found 1 hour ago
$333
Roundtrip
found 1 hour ago
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