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 11 - Aug 15

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    4 nights
    3.5 star property
    8.6/10 - Excellent (380 reviews)
    "A/ C was amazing ! Clean very cute rooms. Loved the brewing coffee maker and the cleaning stuff they left for us. Made the stay comfortable like home ."
    Reviewed June 7, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    Save 100% on your flight
    $1,448
    $1,013
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Sunset Harbor, Key West
  • Jul 26 - Aug 2

    Hyatt Vacation Club at Beach House, Key West + Flight

    Key West
    7 nights
    3.5 star property
    9.4/10 - Exceptional (1,094 reviews)
    "Property well very clean and maintained. Staff was very friendly and accommodating. Rooms had everything you would need and very clean. Great place to stay!"
    Reviewed June 8, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    Save 100% on your flight
    $3,043
    $1,865
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Beach House, Key West
  • Jul 26 - Aug 2

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    7 nights
    3.5 star property
    9.4/10 - Exceptional (1,124 reviews)
    "Excellent stay! Walkable to the Smathers beach... rooms were very clean. Pool has great ocean view. Amenities were good!"
    Reviewed June 9, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    Save 100% on your flight
    $2,432
    $1,511
    per traveler
    found 2 days ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Jul 26 - Aug 2

    The Key West Hotel + Flight

    Key West Historic District
    7 nights
    3.0 star property
    9.2/10 - Wonderful (558 reviews)
    "We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds."
    Reviewed June 7, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    Save 100% on your flight
    $2,853
    $1,841
    per traveler
    found 2 days ago
    The Key West Hotel
  • Jul 26 - Aug 2

    Oceans Edge Key West Resort, Hotel & Marina + Flight

    Stock Island
    7 nights
    4.0 star property
    9.0/10 - Wonderful (1,875 reviews)
    "Great place for a family reunion"
    Reviewed June 9, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    Save 100% on your flight
    $2,118
    $1,486
    per traveler
    found 2 days ago
    Oceans Edge Key West Resort, Hotel & Marina

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 29 to Jun 30
$294 total
Jun 29 - Jun 30
Total with taxes and fees
8.8/10 Excellent! (3,375 reviews)
"Espectacular"

Reviewed on Jun 8, 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
$283 nightly
The price is $319 total per night from Jun 23 to Jun 24
$319 total
Jun 23 - Jun 24
Total with taxes and fees
8.4/10 Very Good! (698 reviews)
"The room was clean the first day. But everyone was complaining about their rooms not being cleaned the whole day and they didn't clean up the next day. Even more we had to call every day. And housekeeping half clean everytime they came We were asked to pay for the daybed. Things that should have ..."

Reviewed on Jun 9, 2026

Casa Marina Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $280 total per night from Jun 17 to Jun 18
$280 total
Jun 17 - Jun 18
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
"Wonderful stay! Highly recommend."

Reviewed on Jun 7, 2026

The Reach Key West, Curio Collection by Hilton
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.