The Meadows Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Property grounds
    Jul 6 - Jul 10

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    4 nights
    3.5 star property
    9.4/10 - Exceptional (1,099 reviews)
    "The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."
    Reviewed May 28, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $1,895
    CA $1,384
    per traveller
    found 5 hours ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Exterior
    Jul 8 - Jul 12

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Beautiful property. Excellent service."
    Reviewed May 15, 2026
    Roundtrip • Montreal (YUL) - Key West (EYW)
    YUL - EYW • 1 stop EYW - YUL • 1 stop
    CA $3,167
    CA $2,019
    per traveller
    found 1 day ago
    Southernmost House - Adult Exclusive
  • Studio, Ocean View | Beach/ocean view
    Aug 6 - Aug 13

    Coconut Beach Resort + Flight

    Old Town Key West
    7 nights
    2.5 star property
    8.8/10 - Excellent (192 reviews)
    "This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun."
    Reviewed May 29, 2026
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $3,608
    CA $2,581
    per traveller
    found 4 hours ago
    Coconut Beach Resort
  • Outdoor pool
    Jul 8 - Jul 12

    The Key West Hotel + Flight

    Key West Historic District
    4 nights
    3.0 star property
    9.2/10 - Wonderful (556 reviews)
    Roundtrip • Montreal (YUL) - Key West (EYW)
    YUL - EYW • 1 stop EYW - YUL • 1 stop
    CA $3,205
    CA $2,351
    per traveller
    found 1 day ago
    The Key West Hotel
  • Outdoor dining
    Aug 8 - Aug 18

    Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays + Flight

    Old Town Key West
    10 nights
    3.0 star property
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $6,209
    CA $4,570
    per traveller
    found 0 hours ago
    Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

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

3 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 $148 per night from Jun 2 to Jun 3
CA $148
CA $166 total
Jun 2 - Jun 3
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Staff were friendly and helpful. Room was clean, cute, bright, and airy."

Reviewed on May 28, 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 $242 per night from Jun 1 to Jun 2
CA $242
CA $303 total
Jun 1 - Jun 2
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The hotel was an older property but nicely maintained our bathroom sink backed up told front desk was taken care of . Located in central areas to local attractions."

Reviewed on May 29, 2026

The Palms Hotel
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 FL
9.2/10 Wonderful! (72 reviews)
"Our stay was very comfortable and cozy. We were able to get around easily with everything within walking distance. Loved the front porch and enjoyed having our coffee/ breakfast and relaxing without disturbances."

Reviewed on Apr 13, 2026

Get rates
Paradise Place by AvantStay | Key West Old Town Condo w/ Shared Pool
See all 2,740 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 . 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.