Search Deals onKey West Vacation Packages
Key West Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Price was $1,769, price is now $1,249 per person
$1,249
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, 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.
The Key West Hotel
Save 100% on your flight
Price was $3,500, price is now $2,131 per person
$2,131
per person
May 13 - May 18
found 1 day ago
Roundtrip flight included
Portland (PDX) 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.
Coconut Beach Resort
Save 100% on your flight
Price was $2,759, price is now $1,958 per person
$1,958
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Ella's Cottages - Key West Historic Inns
Save 100% on your flight
Price was $2,519, price is now $1,831 per person
$1,831
per person
May 13 - May 18
found 1 day ago
Roundtrip flight included
Portland (PDX) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ridley House - Key West Historic Inns
Save 100% on your flight
Price was $2,511, price is now $1,826 per person
$1,826
per person
May 13 - May 18
found 1 day ago
Roundtrip flight included
Portland (PDX) 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.
The Perry Hotel & Marina Key West
Price was $2,328, price is now $1,699 per person
$1,699
per person
May 13 - May 18
found 1 day ago
Roundtrip flight included
Portland (PDX) 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.
Southernmost Beach Resort and Guesthouses
Price was $2,600, price is now $1,901 per person
$1,901
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Key West (EYW)
Book a stay at this beach 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 Southernmost Point are located nearby.
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Save 100% on your flight
Price was $2,145, price is now $1,570 per person
$1,570
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Key West (EYW)
Stay at this cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
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
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.
Mon, Jun 15 - Wed, Jul 1
TPA
Tampa Intl.
EYW
Key West Intl.
$92 Roundtrip, found 4 days ago
$92
Roundtrip
found 4 days ago
Mon, Mar 30 - Wed, Apr 8
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Mon, Apr 13 - Wed, Apr 29
ORD
O'Hare Intl.
EYW
Key West Intl.
$234 Roundtrip, found 17 hours ago
$234
Roundtrip
found 17 hours ago
Mon, Jun 22 - Thu, Jul 9
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$269 Roundtrip, just found
$269
Roundtrip
just found
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