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.
  • Jul 5 - Jul 10

    Hyatt Vacation Club at Beach House, Key West + Flight

    Key West
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,071 reviews)
    "Beautiful place! Had so much staying here for my sister’s bachelorette weekend. We very much enjoyed having a pool and beach to lounge around at. Guests and staff were very friendly during our stay"
    Reviewed May 30, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,811
    $1,270
    per traveler
    found 1 day ago
    Hyatt Vacation Club at Beach House, Key West
  • Aug 8 - Aug 15

    Amelia Home by Avantstay In Historic Old Town w/ Pool + Flight

    Old Town Key West
    7 nights
    3.0 star property
    10/10 - Exceptional (3 reviews)
    "Loved it"
    Reviewed March 20, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    $4,140
    $2,962
    per traveler
    found 12 hours ago
    Amelia Home by Avantstay In Historic Old Town w/ Pool
  • Jul 20 - Jul 31

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

    Key West
    11 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
    $5,439
    $3,923
    per traveler
    found 1 day ago
    Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
  • Aug 18 - Aug 25

    Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub! + Flight

    Old Town Key West
    7 nights
    3.0 star property
    10/10 - Exceptional (6 reviews)
    "Although not on the beach you are a ten min bike ride from most. All restaurants Duval has to offer. The house is cute, clean and the back yard is awesome. We will stay again nextime!"
    Reviewed November 24, 2025
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $2,678
    $1,961
    per traveler
    found 3 hours ago
    Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
  • Aug 16 - Aug 22

    Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays + Flight

    Old Town Key West
    6 nights
    3.0 star property
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $2,580
    $1,892
    per traveler
    found 3 hours ago
    Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

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! (3,341 reviews)
"The property we stayed at was nice. They got us into the room right away and it was conveniently located to Duvall Street. However, the room attendant did not come every day and our shower door would not close all the way which we told them the first day we got there and they never came to fix it. ..."

Reviewed on May 30, 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
$297 nightly
The price is $334 total per night from Jun 27 to Jun 28
$334 total
Jun 27 - Jun 28
Total with taxes and fees
8.4/10 Very Good! (685 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! (1,116 reviews)
"The property was very nice the only complaint is that with paid for an ocean view room and on 2 of our 4 days a cruise ship docked and obscured the view from 8am to 5pm."

Reviewed on May 29, 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.