The Meadows Vacation Packages

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Top Holiday Package Deals in The Meadows

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was CA $1,990, price is now CA $1,511 per person
CA $1,511
per person
May 15 - May 18
found 24 hours ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,230 reviews)
Winslow’s Bungalows offers a delightful stay for guests. It is centrally located for exploring Key West. The staff were very helpful.

Reviewed on Apr 10, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $4,530, price is now CA $2,862 per person
CA $2,862
per person
May 15 - May 18
found 24 hours ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Duval s Duet on Duval by Brightwild

Duval s Duet on Duval by Brightwild

2 out of 5
Old Town Key West
Price was CA $13,392, price is now CA $10,102 per person
CA $10,102
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos

2 out of 5
Old Town Key West
Price was CA $12,862, price is now CA $9,710 per person
CA $9,710
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
Price was CA $2,357, price is now CA $1,782 per person
CA $1,782
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.4/10 Very Good! (595 reviews)
We had a great time. The hotel is beautiful and in a great location. The beach and two pools are perfectly located. A easy walk to Duval st. The rooms are nice but not much storage or closet space for clothing. The showers could use some shelving for personal shower products. The food and drinks are outrageously expensive, so you may wa t to think about dinner and drinks elsewhere. Overall we really loved the place. The staff was amazing. We will come back next year.

Reviewed on Apr 11, 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

Old Town Key West

4 out of top 10 points of interest in this area
3.5/5(8 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.

Find hotels in Old Town Key West

The Meadows Hotel Deals

Authors of Key West Guest House

Authors of Key West Guest House

3 out of 5
725 White St. & Petronia Key West FL
The price is CA $273 per night from Apr 14 to Apr 15
CA $273
CA $307 total
Apr 14 - Apr 15
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
You might want to include a sign for pool hours . We were awoke at 530 am yesterday by a group in the pool being loud right outside our door .

Reviewed on Apr 12, 2026

Authors of Key West Guest House
The Palms Hotel

The Palms Hotel

3 out of 5
820 White St Key West FL
The price is CA $295 per night from May 10 to May 11
CA $295
CA $363 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
Parking is limited. Within walking distance to most sites/restaurants. Clean, quiet and quaint neighborhood. We had to park on street, not too far but is limited.

Reviewed on Apr 12, 2026

The Palms Hotel
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from May 10 to May 11
CA $248
CA $357 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (2,087 reviews)
Clean room, 2 nice pools, everything has been remodeled. Definitely would stay there again.

Reviewed on Apr 12, 2026

Blue Flamingo Resort Key West
See all 2,741 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.
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Frequently asked questions

How much does a The Meadows vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in The Meadows from just CA $1,511. And the more you bundle, the more money you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to The Meadows?
Bundle your flights and hotels, throw in extras such as activities or a rental car, and save with a The Meadows vacation package. You won't just land exciting discounts on your adventure — you'll have loads of choice too. When you book through Expedia, you'll have your pick of over 550 air carriers and 1,000,000 properties all over the world. Your affordable vacation begins right here, right now!
Where should I stay in The Meadows?
Travelers come from all over the world to experience Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in The Meadows. Book a room close to these terrific attractions to make sightseeing easy.
What are the top hotels in The Meadows?
If it's your first visit to The Meadows, book a room at Tropical Old Town Bungalow - Lovely 2nd Floor 1bedroom Unit or Petite Pearl Spacious 1 Bedroom. Both offer comfortable beds and are favorites among many travelers.
How far in advance should I book my The Meadows vacation?
Savvy travelers often book early. You can normally look up international airfares on Expedia up to a year before your flight. If you're purchasing tickets last minute, don't stress. Bargain prices sometimes appear in the last weeks before departure.
What does an Expedia The Meadows travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your perfect The Meadows vacation. You can also add on a few activities and tours once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a The Meadows travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and pick up fantastic discounts. You're not limited to hotels, however. Book with us and choose from oceanfront condos, mountain cabins and even ranches and treehouses!
Can I choose my airline with a The Meadows Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply select the carrier you want and craft the perfect The Meadows escape.
If I'm not able to travel, can I cancel my The Meadows vacation package?
Your situation can change suddenly, so yes, you can. You may be able to cancel and rebook your The Meadows vacation package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your airline, hotel or car rental company may impose a charge. Looking for more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.