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.
3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Oct 10 - Oct 12
2 night stay
Hartford (BDL) to Key West (EYW)
Breeze Airways • Coach
Key West (EYW) to Hartford (BDL)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,347, price is now $944 per person
$944
per person
found 18 hours ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
3.5-star property
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
8.6/10 Excellent! (415 reviews)
Dec 3 - Dec 8
5 night stay
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
American Airlines • Coach
Key West (EYW) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,888, price is now $1,288 per person
$1,288
per person
found 1 day ago
3.0-star property
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
9.4/10 Exceptional! (3 reviews)
Nov 11 - Nov 17
6 night stay
Hartford (BDL) to Key West (EYW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,605, price is now $1,928 per person
$1,928
per person
found 15 hours ago
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
2.0-star property
Bananas Foster by Brightwild Epic Guesthouse
Key West Historic District
No reviews
Dec 3 - Dec 8
5 night stay
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
American Airlines • Coach
Key West (EYW) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $12,111, price is now $9,012 per person
$9,012
per person
found 1 day ago
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
Southwinds Motel
1321 Simonton Street Key West FL
0.27 mi from Old Town Key West
$155 nightly
The price is $174 total per night
$174 total
Sep 10 - Sep 11
Total with taxes and fees
Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. Self parking is offered for USD 22.50 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. Additional amenities include laundry facilities, a picnic area, and a vending machine.
Pool
Breakfast included
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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