Old Town Key West Vacation Packages
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3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Nov 24 - Nov 28
4 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $3,064, price is now $2,088 per person
$2,088
per person
found 1 day ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
3.5-star property
Hyatt Vacation Club at Beach House, Key West
9.4/10 Exceptional! (1,218 reviews)
Nov 17 - Nov 21
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,323, price is now $941 per person
$941
per person
found 1 day ago
3.5-star property
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Old Town Key West
8.8/10 Excellent! (3 reviews)
Oct 10 - Oct 17
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,436, price is now $2,519 per person
$2,519
per person
found 1 day ago
The location to the things we wanted to do was perfect
Reviewed on May 1, 2026
Top rated hotels for your Old Town Key West vacation package
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
0.26 mi from Old Town Key West
$210 nightly
The price is $237 total per night
$237 total
Sep 15 - Sep 16
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this spa hotel include conference space, coffee/tea in a common area, and a computer station.
Pool
Spa
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Free Cancellation
Reserve now, pay when you stay
0.52 mi from Old Town Key West
$306 nightly
The price is $344 total per night
$344 total
Sep 16 - Sep 17
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton features a private beach, a full-service spa, and 2 outdoor pools. Valet parking is offered for USD 50 per day. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and concierge services. Other amenities at this beach resort include a gym, free WiFi in public areas, and conference space.
On private beach
Pool
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Free Cancellation
Reserve now, pay when you stay
0.35 mi from Old Town Key West
$244 nightly
The price is $274 total per night
$274 total
Sep 22 - Sep 23
Total with taxes and fees
Guests of The Reach Key West, Curio Collection by Hilton have access to a private beach, a full-service spa, and an outdoor pool. Valet parking is offered for USD 50 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and concierge services. Other amenities at this beach resort include a gym, meeting rooms, and conference space.
On private beach
Pool
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View all propertiesLowest 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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$42
per adult
94% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
$68
per traveler
92% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend