Sunset Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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.
  • Terrace/patio
    Jul 6 - Jul 10

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    4 nights
    3.5 star property
    8.6/10 - Excellent (371 reviews)
    "Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Miami (MIA)
    YTZ - MIA • 1 stop MIA - YYZ • 1 stop
    CA $1,915
    CA $1,343
    per traveller
    found 1 day ago
    Hyatt Vacation Club at Sunset Harbor, Key West
  • Exterior
    Jun 25 - Jun 29

    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 • Halifax (YHZ) - Key West (EYW)
    YHZ - EYW • 1 stop EYW - YHZ • 1 stop
    CA $2,906
    CA $1,779
    per traveller
    found 1 day ago
    Southernmost House - Adult Exclusive
  • Property grounds
    Aug 10 - Aug 16

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,092 reviews)
    "Excellent room. Clean and walking distance from airport. Great restaurants in walking distance as well. Staff was sufficient but not going the extra mile in terms of getting needs met."
    Reviewed May 23, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - MIA • Nonstop MIA - YUL • Nonstop
    CA $3,140
    CA $1,995
    per traveller
    found 10 hours ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Outdoor pool
    Aug 2 - Aug 7

    The Key West Hotel + Flight

    Key West Historic District
    5 nights
    3.0 star property
    9.2/10 - Wonderful (555 reviews)
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $3,059
    CA $2,188
    per traveller
    found 1 day ago
    The Key West Hotel
  • Exterior
    Jul 26 - Aug 2

    Ridley House - Key West Historic Inns + Flight

    Key West Historic District
    7 nights
    3.5 star property
    9.2/10 - Wonderful (911 reviews)
    "Very nice! Will stay again!"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - Fort Lauderdale (FLL)
    YYZ - FLL • Nonstop MIA - YYZ • Nonstop
    CA $2,073
    CA $1,532
    per traveller
    found 23 hours ago
    Ridley House - Key West Historic Inns

Where to stay in Sunset Key

Find the best Sunset Key areas and neighborhoods for the activities you enjoy most. Learn more about Sunset Key
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

Sunset Key Hotel Deals

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 $185 per night from May 27 to May 28
CA $185
CA $286 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (2,268 reviews)
"Staff was on point , awesome time , would do it again ."

Reviewed on May 23, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $335 per night from May 28 to May 29
CA $335
CA $477 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (3,327 reviews)
"The resort was very nice. The pools were great and the room was updated and clean. Great location on Duval Street. Highly recommend."

Reviewed on May 22, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $311 per night from May 31 to Jun 1
CA $311
CA $437 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (1,800 reviews)
"Resort fee is quite high for the amenities offered-we didn’t use the shuttle, nor did we take advantage of slushies or popsicles as they are available for a short period of time. Welcome drink was never offered, nor was parking pass. Happened to observe in other vehicles and inquired. The room was ..."

Reviewed on May 23, 2026

Margaritaville Beach House Key West
See all 2,721 properties in Sunset Key
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Sunset Key vacation package cost?
Create unforgettable memories with our Sunset Key vacation packages, which start from only . Handpick the flights and hotels that fit your travel plans. Then, add on a couple of sightseeing tours for a memorable escape.
How do I get a cheap travel package to Sunset Key?
Our Sunset Key vacation packages offer plenty of savings for the savvy traveler. For the best deals, simply bundle your hotel, flights and tours into one neat package. But low prices are just the beginning of your next epic adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 hotel options globally to select from. Whatever your style or budget, there's a vacation package here just for you.
Where should I stay in Sunset Key?
Most visitors who travel to Sunset Key put both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their itineraries. Why not book a hotel near these top attractions?
How far in advance should I book my Sunset Key vacation?
It can be tricky to know exactly when is the ideal time to book your Sunset Key vacation. But typically the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to fret! There are fabulous bargains popping up on Expedia all the time.
What does an Expedia Sunset Key travel package include?
Flights, rental cars and hotels — you'll discover them all here. With Expedia, you can shape your Sunset Key travel package the way you want. All you have to do is determine just what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the bigger the savings!
What should I know before booking a Sunset Key travel package?
Whether it's relaxation or adventure you're chasing, a Sunset Key vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Sunset Key Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're in control. We have access to more than 550 partner airlines all over the world, so you have lots of choice when organizing your Sunset Key escape.
If I'm not able to travel, can I cancel my Sunset Key vacation package?
If your travel plans in Sunset Key have been upended, it's a relief to know that it's possible to cancel or amend your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.