Old Town Key West Vacations

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Your Old Town Key West Vacation

Organizing your next exciting getaway just got a whole lot easier with a vacation package to Old Town Key West. Take in the best this neighborhood has to offer while making precious memories you'll replay for years. Some leading nearby attractions to check out during your trip to Old Town Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help put your plans into action. Book your ideal Old Town Key West vacation now.

Price found within the past 48 hours. Click for updated prices.
  • Aug 23 - Aug 29

    Hyatt Vacation Club at Beach House, Key West + Flight

    Key West
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,076 reviews)
    "I would say it's time to remove all carpets. The first unit we had, smelled terrible, like wet clothing. The hotle staff quickly moved us and ensured we were comfortable."
    Reviewed June 1, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,604
    $1,013
    per traveler
    found 1 day ago
    Hyatt Vacation Club at Beach House, Key West
  • Aug 16 - Aug 22

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,102 reviews)
    "The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."
    Reviewed May 28, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $2,065
    $1,234
    per traveler
    found 1 day ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Aug 16 - Aug 22

    Lighthouse Hotel - Key West Historic Inns + Flight

    Old Town Key West
    6 nights
    3.5 star property
    9.0/10 - Wonderful (949 reviews)
    "Staff is friendly, attentive and helpful. Continental Breakfast is fresh and the perfect start for a day of adventure. We were there for a destination wedding at the Hemingway House that is right across the street. Location could not have been any better."
    Reviewed June 1, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,620
    $1,093
    per traveler
    found 1 day ago
    Lighthouse Hotel - Key West Historic Inns
  • Jul 21 - Jul 28

    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 - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $3,820
    $2,692
    per traveler
    found 1 day ago
    Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
  • Aug 18 - Aug 24

    Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool! + Flight

    Old Town Key West
    6 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Loved the closeness to Duval st and the privacy "
    Reviewed October 17, 2025
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $3,768
    $2,684
    per traveler
    found 20 hours ago
    Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Where to stay in Old Town Key West

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

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from Jun 8 to Jun 9
$294 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (3,350 reviews)
"Are room was ok. There was an unusable beach. The smell was terrible. The restaurants were not kid friendly and made no effort to accommodate a 10 year old. Had 3 different menus and wouldn't cook anything that was on the bar menu that used the same kitchen. All kinds of additional fees at checkout. ..."

Reviewed on Jun 1, 2026

Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $359 total per night from Jun 2 to Jun 3
$359 total
Jun 2 - Jun 3
Total with taxes and fees
8.4/10 Very Good! (687 reviews)
"We were really disappointed by the beach. It’s rocky and was covered in seaweed (during our visit). The pools are beautiful, staff was lovely. The room was enormous and well maintained. I just wish we had more transparency regarding the condition of the beach."

Reviewed on May 30, 2026

Casa Marina Key West, Curio Collection by Hilton
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
Total with taxes and fees
9.2/10 Wonderful! (1,123 reviews)
"Very clean room and great staff, the restaurant is great, Lolita's has great food and a great ocean front view. Location is the best in Key West."

Reviewed on Jun 1, 2026

Opal Key Resort & Marina, Key West
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.