Downtown Key West Vacations

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Your Downtown Key West Vacation

Our Downtown Key West vacation packages are a time-saving and convenient way to arrange and book your next escape. Experience the magic of this unique neighborhood without the bother of planning everything yourself. Your trip to Downtown Key West wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Don't just imagine it — make it a reality! Book your ideal Downtown Key West vacation with Expedia and get to where you're going your way.

Price found within the past 48 hours. Click for updated prices.
  • Aug 12 - Aug 15

    Hyatt Vacation Club at Beach House, Key West + Flight

    Key West
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,061 reviews)
    "Nice clean room. one smoking area is not enough. no on site restaurant or snack bar of vending for snacks. "
    Reviewed May 19, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    $1,134
    $814
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Beach House, Key West
  • Aug 12 - Aug 15

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,090 reviews)
    "Property was amazing. Room was clean, staff was very friendly. Has a great time at the pool. "
    Reviewed May 19, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,317
    $902
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Aug 6 - Aug 10

    The Key West Hotel + Flight

    Key West Historic District
    4 nights
    3.0 star property
    9.2/10 - Wonderful (555 reviews)
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,919
    $1,331
    per traveler
    found 2 days ago
    The Key West Hotel
  • Aug 12 - Aug 15

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    3 nights
    3.5 star property
    8.6/10 - Excellent (371 reviews)
    "Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"
    Reviewed May 18, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,353
    $942
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Sunset Harbor, Key West
  • Jul 11 - Jul 18

    Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front + Flight

    Key West
    7 nights
    3.0 star property
    9.4/10 - Exceptional (3 reviews)
    "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 March 26, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYW1 stop EYW - ATL1 stop
    Save 100% on your flight
    $3,891
    $2,866
    per traveler
    found 1 day ago
    Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Where to stay in Downtown Key West

Find the best Downtown Key West areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Key West

Downtown Key West Hotel Deals

Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
$159 nightly
The price is $179 total per night from May 20 to May 21
$179 total
May 20 - May 21
Total with taxes and fees
9.2/10 Wonderful! (1,152 reviews)
"One of the best hotel beds I have ever slept on. I will be contacting management to ask for the brand so I can buy one. Excellent Hotel!! Great Location!!"

Reviewed on May 19, 2026

Heron House - Adult Only
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from May 26 to May 27
$234 total
May 26 - May 27
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Steps from Duval, quiet, wonderful people & very attentive. Breakfast included, wine & cheese from 5-7 great way to mingle & meet other guests. Several people stayed here before & continue to return. They let us stay & use all amenities before & after checkout."

Reviewed on May 18, 2026

The Cabana Inn Key West - Adults Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
$195 nightly
The price is $219 total per night from May 20 to May 21
$219 total
May 20 - May 21
Total with taxes and fees
8.2/10 Very Good! (1,025 reviews)
"Breakfast fresh nice clean room"

Reviewed on May 19, 2026

Pegasus International Hotel
Lowest 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.