Sunset Key Vacations from $1,749

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Your Sunset Key Vacation

Let our Sunset Key vacation packages take you to a destination where long-lasting memories are waiting to be made. While it's especially renowned for its coastal beaches, there's plenty to love about this neighborhood. Not sure where to go during your trip to Sunset Key? Nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are great places to start. No matter what your dream Sunset Key vacation may look like, you can turn it into reality with Expedia.

The Latest Sunset Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Gardens Hotel

The Gardens Hotel

Old Town Key West
$1,749
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,329
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
$2,757
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West
Save 100% on your flight
$2,695
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (3 reviews)
Loved it

Reviewed on Mar 20, 2026

Duval s Duet on Duval by Brightwild

Duval s Duet on Duval by Brightwild

Old Town Key West
Save 100% on your flight
$7,219
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
No reviews

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
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.

Sunset Key Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$168 nightly
$189 total
Sep 30 - Oct 1
Total with taxes and fees
Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$229 nightly
$258 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (3,636 reviews)
"A+"

Reviewed on Sep 28, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$265 nightly
$298 total
Sep 30 - Oct 1
Total with taxes and fees
Margaritaville Beach House Key West
See all 2,662 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.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$61
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Key West

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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.