Sunset Key Vacation Packages 2026 from $691

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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.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$691

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,397 reviews)

Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.

Reviewed on Sep 1, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,922

per person

Nov 4 - Nov 7

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

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$1,027

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (951 reviews)

Stayed here for a birthday celebration and it was perfect. Breakfast by the pool every morning, rooms were big, and we didn't hear anything throughout our stay so we slept well!

Reviewed on Sep 2, 2026

Ella's Cottages - Key West Historic Inns

Old Town Key West

$758

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (494 reviews)

It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.

Reviewed on Sep 1, 2026

Kona Kai Oasis

Old Town Key West

Save 100% on your flight

$844

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8/10 Very Good! (651 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

$210 nightly

$237 total

Sep 9 - Sep 10

Total with taxes and fees

8.6/10 Excellent! (3,562 reviews)

"From check in and check out everything in between this Hotel was everything and more during our weekend girls trip get away!! We will not hesitate to book again in a few months!!"

Reviewed on Sep 2, 2026

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$185 nightly

$208 total

Sep 3 - Sep 4

Total with taxes and fees

8.6/10 Excellent! (2,483 reviews)

"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There ..."

Reviewed on Sep 1, 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 16 - Sep 17

Total with taxes and fees

8.8/10 Excellent! (1,798 reviews)

"Loved our bartender. So many kids lol. Not a fan"

Reviewed on Sep 1, 2026

See all 2,682 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.