Meadows Vacations from $763
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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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,135, price is now $763 per person
$763
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,261 reviews)
Continental.breakfast . Clean rooms
Wooden bungalow, beautifully decorated
Reviewed on May 9, 2026
Southernmost House - Adult Exclusive
Old Town Key West
Save 100% on your flight
Price was $2,353, price is now $1,301 per person
$1,301
per person
Jun 10 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We love the location and the landscaping. The breakfast was amazing. They go above and beyond to accommodate their guests. Everything was exceptional.
Reviewed on May 8, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $3,165, price is now $1,976 per person
$1,976
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (365 reviews)
Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger.
Location was awesome… just a couple blocks to everything!
Reviewed on May 6, 2026
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,438, price is now $938 per person
$938
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,059 reviews)
The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)
Reviewed on May 5, 2026
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,535, price is now $1,016 per person
$1,016
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
Nice to have laundry in the apartment
Reviewed on May 7, 2026
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(229 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
Authors of Key West Guest House
725 White St. & Petronia Key West FL
$179 nightly
The price is $201 total per night from May 11 to May 12
$201 total
May 11 - May 12
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Property was great. Location was nice, close enough but not too close to all the craziness of Duval St.
Reviewed on May 4, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from May 26 to May 27
$234 total
May 26 - May 27
Total with taxes and fees
8.4/10 Very Good! (2,209 reviews)
All good
Reviewed on May 8, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $267 total per night from Jun 8 to Jun 9
$267 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (1,810 reviews)
Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.
Reviewed on May 7, 2026
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
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
82% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.