Sunset Key Vacation Packages 2026 from $728

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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.

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$728

per person

Sep 19 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.2/10 Very Good! (2,329 reviews)

Room was beautifully decorated and more than enough space for our family. The shower we had was extremely small though, so just a word of caution for us bigger-boned folk! I made it work but it wasn't easy. Breakfast is at the restaurant and was good. Pool is great, private beach is great. We lived all the wildlife around! We definitely recommend.

Reviewed on Aug 13, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$927

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

The staff was fantastic and we loved the hotel!!! Great location!

Reviewed on Aug 13, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,539

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,157

per person

Sep 18 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,214 reviews)

Great location with a view of the sea from the pool. Room was perfect size for family of 5 with everything you needed.

Reviewed on Aug 13, 2026

Kona Kai Oasis

Old Town Key West

Save 100% on your flight

$1,125

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.2/10 Very Good! (642 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

$203 nightly

$228 total

Sep 1 - Sep 2

Total with taxes and fees

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$188 nightly

$212 total

Aug 31 - Sep 1

Total with taxes and fees

8.6/10 Excellent! (2,430 reviews)

"The room was ok. Hot shower comfy bed. Says it is on the beach not what I expected at all. Swam at other better beaches"

Reviewed on Aug 13, 2026

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$136 nightly

$153 total

Aug 17 - Aug 18

Total with taxes and fees

8.2/10 Very Good! (2,333 reviews)

"Room was beautifully decorated and more than enough space for our family. The shower we had was extremely small though, so just a word of caution for us bigger-boned folk! I made it work but it wasn't easy. Breakfast is at the restaurant and was good. Pool is great, private beach is great. We lived ..."

Reviewed on Aug 13, 2026

See all 2,672 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.