Meadows Vacations from $628
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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.
Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,712, price is now $981 per person
$981
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (479 reviews)
Property has a very cozy feel
Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room.
Reviewed on Aug 24, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,530, price is now $912 per person
$912
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,011 reviews)
We loved our stay here. Everything was clean, comfortable, and well appointed. The pool was gorgeous and spacious, and the food and drinks from the bar/cafe were tasty. The only complaint we had was how loud the carts rolling by outside of our room could be heard inside our room. I think a room that is not located right next to the offices would be quieter.
Reviewed on Aug 31, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,896, price is now $1,796 per person
$1,796
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (367 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!
Reviewed on Aug 31, 2025
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $2,541, price is now $1,582 per person
$1,582
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (812 reviews)
Loved the complimentary breakfast provided daily, though choices are more limited during the week when we went than on the weekends. Pool was nice and refreshing during the very hot and humid weather, but they need more lounge chairs for guests. Despite the issue with our cards not allowing us access to our rooms the first night and second day and having to move rooms, we thoroughly enjoyed our stay and would highly recommend this property to others for future stays.
Reviewed on Aug 27, 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
Beachside Resort & Residences
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
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,699 reviews)
"In general, I enjoyed my stay at Ocean Edge Resort. The room was clean and comfortable with a nice view of the ocean and the Marina. The property in general looks beautiful with an island vibe touch and it’s really pleasant to walk around. The staff at the front desk were friendly and polite. My ..."
Reviewed on Aug 31, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Sep 15 to Sep 16
$264 total
Sep 15 - Sep 16
Total with taxes and fees
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 Sushi Sunset Cruise with Complementary Drinks
$75
per adult
98% of travellers recommend
Key West Tiki Bar Sunset Cruise (by the seat)
$81
per adult
100% of travellers recommend
Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat
$564
per traveler
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.