Search Deals onRaccoon Key Vacation Packages
Raccoon Key Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,849, price is now $1,351 per person
$1,351
per person
Dec 9 - Dec 13
found 24 hours 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.
I loved the outdoor area and pool! We utilized the grill area as we had a big party and it was great!!
I would have game 5 stars for everything but I was not advised during check in that cleaning staff do not come in daily. I had to call every day for towels (they were delivered quickly) but the old towels and trash were not removed from the room, even after I requested it from the front desk.
Reviewed on Sep 28, 2026
The Key West Hotel
Save 100% on your flight
Price was $2,652, price is now $1,818 per person
$1,818
per person
Dec 19 - Dec 23
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.
The Gardens Hotel
Save 100% on your flight
Price was $2,944, price is now $2,079 per person
$2,079
per person
Dec 19 - Dec 23
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.
It is a GREAT property in Key West, right in the center of the action.
Reviewed on Sep 28, 2026
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Save 100% on your flight
Price was $2,814, price is now $2,035 per person
$2,035
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Absolutely loved the Privacy and that we were right next to Cuban Coffee Queen! This is a nice little place to stay with great privacy. It was clean, had the little things, like Q-Tips!
Will definitely stay there next year!
Reviewed on Aug 27, 2026
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $2,868, price is now $2,082 per person
$2,082
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .
Reviewed on Mar 26, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Price was $2,104, price is now $1,548 per person
$1,548
per person
Dec 19 - Dec 23
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, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Commodore s Compound by Brightwild Huge Home
Save 100% on your flight
Price was $17,341, price is now $13,234 per person
$13,234
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Mallory Square are located nearby.
Bananas Foster by Brightwild Epic Guesthouse
Save 100% on your flight
Price was $21,279, price is now $16,293 per person
$16,293
per person
Dec 19 - Dec 26
found 2 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Mallory Square are located nearby.
Raccoon Key Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Raccoon Key Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Oct 18 - Wed, Oct 28
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$86 Roundtrip, found 17 hours ago
$86
Roundtrip
found 17 hours ago
Sat, Oct 17 - Tue, Oct 27
TPA
Tampa Intl.
EYW
Key West Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Mon, Nov 2 - Fri, Nov 6
BOS
Logan Intl.
EYW
Key West Intl.
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Mon, Nov 9 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$344 Roundtrip, found 17 hours ago
$344
Roundtrip
found 17 hours ago
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