Old Town Key West Vacation Packages
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Top Old Town Key West vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
8.6/10 Excellent! (415 reviews)
Nov 29 - Dec 6
7 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 $2,897, price is now $1,857 per person
$1,857
per person
found 1 day ago
Room was great for long stays and families. A little outdated but the location was amazing! Easy walk to Mallory square and Duval street. Only complaint is a rooster waking us at 5 am but that’s Key West!
Reviewed on Sep 6, 2026
3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Nov 21 - Nov 28
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • Coach
Price was $4,666, price is now $3,038 per person
$3,038
per person
found 1 day ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
3.5-star property
Ridley House - Key West Historic Inns
Key West Historic District
9.2/10 Wonderful! (952 reviews)
Nov 29 - Dec 6
7 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 $2,846, price is now $2,025 per person
$2,025
per person
found 1 day ago
4.0-star property
Parrot Key Hotel & Villas
Northside Resort
9/10 Wonderful! (1,464 reviews)
Oct 23 - Oct 26
3 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Price was $1,922, price is now $1,385 per person
$1,385
per person
found 1 day ago
I liked the place, the waterfront building allowed us to see a beautiful sunset. The amenities were okay, I just stayed a day and the restaurant was closed.
Reviewed on Sep 7, 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 14 - Sep 15
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
$272 nightly
The price is $306 total per night
$306 total
Sep 15 - Sep 16
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
$246 nightly
The price is $277 total per night
$277 total
Sep 28 - Sep 29
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