The Meadows Vacations from $665

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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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,035, price is now $665 per person
$665
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9.4/10 Exceptional! (1,008 reviews)
This vacation was a real treat for us, long overdue. The staff certainly was helpful and pleasant. The screened in porches were very nice. There was always something each day at the resort to do along with other excursions to choose from. We most definitely will be back!

Reviewed on Aug 27, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,000, price is now $1,183 per person
$1,183
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Fantastic staff, always smiling. Great amenities, super clean, fantastic location.

Reviewed on Aug 25, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,603, price is now $949 per person
$949
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,008 reviews)
It was nice, all we needed for vacation. We had a great time!!!!

Reviewed on Aug 27, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $2,804, price is now $1,787 per person
$1,787
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
I had a great stay at the Perry. The concierge Jeremy set me up on some great excursions. Food and staff were good. I would go back next time. I’m in Key West.

Reviewed on Aug 27, 2025

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $2,369, price is now $1,550 per person
$1,550
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,007 reviews)
We stayed at Ibis Bay Resort and had such a unique Key West experience. The resort has a lot of character—bright, colorful decor, fun murals, and a true tropical vibe that makes it feel different from a standard hotel.

Reviewed on Aug 27, 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
Key West Historic District

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.

Find hotels in Old Town Key West

The Meadows Hotel Deals

The Palms Hotel

The Palms Hotel

3 out of 5
820 White St, Key West, FL
$139 nightly
The price is $156 total per night from Sep 1 to Sep 2
$156 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
July 2025
"Nice place to stay. Rooms are small, so if you have more than 2 adults, it can be tight. Luggage is where it gets tight. Nice breakfast downstairs by the pool. Full service bar opens in the evening. Weather was accommodating so we sat outside to enjoy the bar. Swimming pool is one of the biggest ..."

Reviewed on Aug 20, 2025

The Palms Hotel
Authors of Key West Guest House

Authors of Key West Guest House

3 out of 5
725 White St. & Petronia, Key West, FL
$99 nightly
The price is $111 total per night from Sep 15 to Sep 16
$111 total
Sep 15 - Sep 16
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Lovely place, clean, quiet- friendly front desk! Loved how it’s tucked in and gates are locked at night making you feel safe! Great location! We will definitely come back!"

Reviewed on Aug 23, 2025

Authors of Key West Guest House
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Sep 2 to Sep 3
$207 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (1,493 reviews)
"The rooms were grand"

Reviewed on Aug 27, 2025

Beachside Resort & Residences
See all 2,772 properties in The Meadows
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.

The Unitarian Universalist Fellowship of Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.