The Meadows Vacations from $814
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Your The Meadows Vacation
Make travel planning simple by creating a vacation package to The Meadows. We'll take care of all the details, so you can focus on soaking up everything this neighborhood has to offer. Your trip to The Meadows wouldn't be complete without seeing major attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Stop dreaming and start doing. When you're ready to book your ideal vacation to The Meadows, Expedia is here to help.
The Latest The Meadows Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,335, price is now $814 per person
$814
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Staff was friendly and accommodating. The concierge booked trips for us and made some great recommendations for us.
Reviewed on Oct 8, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,808, price is now $1,057 per person
$1,057
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
The room was clean and the facilities lovely. We enjoyed our stay.
Reviewed on Oct 12, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,779, price is now $1,093 per person
$1,093
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
The pool was lovely!
Reviewed on Oct 12, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,903, price is now $1,213 per person
$1,213
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (375 reviews)
We really enjoyed our stay at Ella’s Cottages. It is a short walk to Duvall Street with lots of dining options close by. The suites were tucked into a beautifully landscaped property. I truly felt transported to a tropical island sanctuary. There were beach/pool towels on the lounge chairs by the pool. The pool itself is small but very clean and refreshing after a hot day. There were also tables in the pool area to dine or gather.
We upgraded our room to a larger room with a patio. The bathroom was nicely updated and very clean. Our bedroom area also was nicely updated and clean. The window AC unit worked hard to cool our room on the lowest setting. The ceiling fan helped.
The staff was very friendly and helped us find good suggestions of places to eat.
The continental breakfast was: essentially it’s a basket of croissants or bagels, bottled orange juice, yogurt cups, coffee, cheese packets, detox shots and two egg bites.
I would highly recommend Ella’s Cottages and would stay here again.
Reviewed on Sep 30, 2025
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,682, price is now $1,728 per person
$1,728
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (496 reviews)
My wife and I have come to KeyWest for years, this by far the nicest and affordable with great music and staff. It's our new go to place!
Reviewed on Oct 3, 2025
Where to stay in The Meadows
Find the best The Meadows areas and neighborhoods for the activities you enjoy most. Learn more about The Meadows
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
The Meadows Hotel Deals
The Palms Hotel
820 White St, Key West, FL
$162 nightly
The price is $182 total per night from Oct 13 to Oct 14
$182 total
Oct 13 - Oct 14
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Palms Hotel is a quaint, adorable, festive, colorfully Keysie, affordable hotel in the middle of Key West making it easily walkable. We really enjoyed the included breakfast and assistance when we accidentally locked ourselves out of the room. Thank you Palms Hotel, we’ll be back!"
Reviewed on Oct 5, 2025
Authors of Key West Guest House
725 White St. & Petronia, Key West, FL
$99 nightly
The price is $111 total per night from Oct 13 to Oct 14
$111 total
Oct 13 - Oct 14
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Clean room with enough space to spend the weekend"
Reviewed on Oct 10, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $213 total per night from Oct 13 to Oct 14
$213 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (1,728 reviews)
"Exceeded our expectations. Restaurant was amazing, everything was clean and up to date. They kept open communication via text messages daily. I am a night shift health care provider, I cannot tell you how much I needed this mini-vacay."
Reviewed on Oct 9, 2025
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.
Discover the most popular places to visit in The Meadows
The Unitarian Universalist Fellowship of Key West
Find out about the history of Key West with a stop at The Unitarian Universalist Fellowship of Key West. Amble around the area's seaside or seek out the biking trails.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.