Meadows Vacations from $720
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Your Meadows Vacation
Reserving a Meadows vacation package is a wonderful way to become acquainted with this unique neighborhood. From its must-visit places to its lesser-known delights, you won't be short of adventures. Want to head out and see the sights during your trip to Meadows? Be sure to stop by nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. No matter what your dream Meadows vacation may look like, you can make it a reality with Expedia.
The Latest Meadows Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,176, price is now $720 per person
$720
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
Definitely have to say the staff was so nice makeable helpful. We even decide to extend our stay
Reviewed on Oct 11, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,319, price is now $780 per person
$780
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Clean rooms and property. The grounds were so clean and taken care of. The landscape was so lush and exquisite. I loved everything about this property. Will be back.
Reviewed on Oct 13, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,237, price is now $751 per person
$751
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
Very low-key beautiful, stunning property. The great Jacuzzi bathtub was a highlight, after long days of being in the sun walking or excursions. The Jacuzzi bath tub will bring us back to life ! The pool and Jacuzzi and all the other amenities were just as great. The spacious rooms and huge balconies,you & the family could eat dinner watching the sunset.
Reviewed on Oct 14, 2025
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,773, price is now $1,141 per person
$1,141
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,005 reviews)
Everything was excellent, except poor TV service in room.
Reviewed on Oct 13, 2025
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $1,386, price is now $912 per person
$912
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (347 reviews)
Truly beautiful custom century hotel, sitting on one of the few beaches in Key West
Reviewed on Oct 12, 2025
Where to stay in Meadows
Find the best Meadows areas and neighborhoods for the activities you enjoy most. Learn more about 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.
Meadows Hotel Deals
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 $212 total per night from Oct 28 to Oct 29
$212 total
Oct 28 - Oct 29
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
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$234 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,787 reviews)
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"
Reviewed on Oct 13, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
$235 nightly
The price is $264 total per night from Oct 28 to Oct 29
$264 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (1,770 reviews)
"Property was fun, inviting and a great place to relax after a day in Old Town Key West. Shuttle to Old Town was great, food at Margaritaville was very good, staff very friendly. Jimmy Buffett tunes playing all the time was perfect!"
Reviewed on Oct 8, 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 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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.