Sunset Key Vacation Packages 2026 from $1,100

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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 Southernmost Inn - Adults Only

Old Town Key West

$1,100

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (1,432 reviews)

We had an awesome stay. Staff were kind and helpful. Pool was very nice and clean. We will definatley book here again on our next trip to Key West.

Reviewed on Sep 15, 2026

The Key West Hotel

Key West Historic District

$3,460

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,347

per person

Oct 30 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,409

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (496 reviews)

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,717

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,226 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 Key West Tropical Forest and Botanical Garden.

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$239 nightly

$269 total

Sep 28 - Sep 29

Total with taxes and fees

8.6/10 Excellent! (3,604 reviews)

"Booked this place for the location and how many pools they had. Didn’t know until we got there that the largest pool was under renovation and completely out of service. Not the end of the world but this made the other 2 pools (combined they were the size of the 1 that was closed) more cramped. Then ..."

Reviewed on Sep 15, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$160 nightly

$180 total

Sep 17 - Sep 18

Total with taxes and fees

8.6/10 Excellent! (2,674 reviews)

"It was a nice hotel. It was very clean quiet they had two Swimming Pool pools so that made it nice for the kids at one pool primarily and the adults at the other the walk-up bars were nice and close."

Reviewed on Sep 16, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$234 nightly

$263 total

Sep 30 - Oct 1

Total with taxes and fees

See all 2,685 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.