The Meadows Vacations from $664
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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.
Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $993, price is now $664 per person
$664
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,289 reviews)
Toilet seat was broken and door handle to refrigerator is broken as well when we first checked in. They did however, put us in a different room immediately so problem was solved.
Reviewed on Jul 14, 2026
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,598, price is now $1,024 per person
$1,024
per person
Oct 3 - Oct 10
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
The Perry Hotel is one of a kind in the best ways possible. The hotel staff went above and beyond to exceed our expectations. They were all very professional, friendly, helpful and knowledgeable. The hotel is kept up very well. I highly recommend The Perry Hotel if you’re looking for a peaceful, serene and one of a kind experience in Key West.
Reviewed on Jul 14, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $1,619, price is now $1,083 per person
$1,083
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.
Reviewed on Jun 7, 2026
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,754, price is now $1,250 per person
$1,250
per person
Oct 3 - Oct 10
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,199 reviews)
Poole was dirty, the water in the pool was hot. Pool felt warmer than the air temp.
Reviewed on Jul 14, 2026
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was $1,096, price is now $788 per person
$788
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (951 reviews)
Our stay was amazing! The property was beautiful, spotless, and conveniently located close to all the key attractions. The staff was incredibly friendly and welcoming, making us feel right at home. A special shoutout to Alejandro at the bar he provided exceptional service, made fantastic drinks, and truly made our experience even more memorable. We can’t wait to come back!
Reviewed on Jul 13, 2026
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
4 out of top 10 points of interest in this area
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
Authors of Key West Guest House
725 White St. & Petronia Key West FL
$119 nightly
The price is $134 total per night from Aug 13 to Aug 14
$134 total
Aug 13 - Aug 14
Total with taxes and fees
9.2/10 Wonderful! (1,027 reviews)
"Room was nice Shower needs work as it was sagging in the basin w a crack. Not good. Facility overall needs some repairs. Breakfast was included for a good value. Plunge pool jacuzzi had half working jets. Did get surprised w a roach in the tea bags. Told the staff and they did not apologize or seem ..."
Reviewed on Jul 15, 2026
The Palms Hotel
820 White St Key West FL
$180 nightly
The price is $202 total per night from Aug 2 to Aug 3
$202 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (1,012 reviews)
"Personas atentas , lo difícil es para parquearse, Muy lejos y que el área de la piscina cierra muy temprano."
Reviewed on Jul 13, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $246 total per night from Jul 16 to Jul 17
$246 total
Jul 16 - Jul 17
Total with taxes and fees
8.6/10 Excellent! (2,344 reviews)
"Great location, great service and very clean."
Reviewed on Jul 14, 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.
Stay near popular The Meadows attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.