The Meadows Vacations from $2,123

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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.
Douglas House - Adults Only

Douglas House - Adults Only

Old Town Key West
Save 100% on your flight
$2,123
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (542 reviews)
Loved our little private porch however the construction next door made it unbearable. Not the fault of the property. The room was spacious and the location was wonderful. The pool is well maintained and a nice oasis after a hot, busy day. Be aware parking is around the corner and very expensive. It cost us $100 for 3 days. The staff was friendly Overall an enjoyable stay and I would sty here again

Reviewed on Oct 11, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
$2,987
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West
Save 100% on your flight
$5,558
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Key West Historic District
Save 100% on your flight
$2,344
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Key West (EYW)
2/10 (1 review)
The listing says this property is “on beach property,” but it is not on the beach or even close to a beach, which was very misleading. While we were staying there, the pool was also resurfaced. We were told that it was a “last-minute” discovery that the pool needed to be closed, but this significantly affected our stay. We also had trouble getting ahold of anyone when we had questions or concerns. Calls to the management/maintenance contact went unanswered, and no one returned our calls. Another issue was the condition of the balconies. We were on one of the lower floors, and whenever the guests above us used their deck, dirt and sand would fall down onto ours while we were sitting outside. It made it very unpleasant to actually use the outdoor space. Overall, the property description was misleading, the unexpected pool closure was disappointing, communication was poor, and the balcony situation made the stay less enjoyable than expected.

Reviewed on Sep 12, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Save 100% on your flight
$2,680
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 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
A white building with shutters, palm trees, and a lawn.

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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.

A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

The Meadows Hotel Deals

Authors of Key West Guest House

Authors of Key West Guest House

725 White St. & Petronia Key West FL
$139 nightly
$156 total
Oct 15 - Oct 16
Total with taxes and fees
Authors of Key West Guest House
The Palms Hotel

The Palms Hotel

820 White St Key West FL
$172 nightly
$193 total
Oct 15 - Oct 16
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Loved the small hotel setting! Friendly staff, great location, nice to have breakfast."

Reviewed on Oct 11, 2026

The Palms Hotel
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
$265 nightly
$298 total
Oct 15 - Oct 16
Total with taxes and fees
Margaritaville Beach House Key West
See all 2,702 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.

Stay near popular The Meadows attractions

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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.