Name: Southernmost Beach Resort and Guesthouses
Price range: $352 total
Rating: 8.8

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

Save 100% on your flight

$885

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,248 reviews)

We’ve stayed in key west many many times first time at this particular location. Pros: the woman at the Front Desk were very friendly. The property is beautiful. Breakfast was surprisingly good. Cons: ugh Keith at the bar. Total downer. Every. Day. He yelled at all patrons at the bar one day too. No towels by the pool. Ever. Location - noisy. Not Relaxing. Also you are .5 mile from everything. Which Is either convenient or not depending on your needs. The rooms - meh. Clean. But it’s a room. Nothing special. Drain didn’t drain. We got 2 towels total for 2 people. No soap. But we bring some just in case. We specifically asked for outdoor area when booking - our outdoor area was two chairs in a common walkway - total bummer. So be mindful of that when booking. Having stayed at other places on the island we won’t be back

Reviewed on May 4, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,247

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,006 reviews)

The accommodation was very nice! Great property location and extremely clean. For a 100 year old mansion, it was in great shape! It’s right next door to the southern most point buoy! Walkable to Mallory square. The parking lot is only for guests and although there was a charge, it was cheaper than parking in Mallory square!

Reviewed on Apr 27, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,135

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,059 reviews)

The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)

Reviewed on May 5, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,467

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (552 reviews)

The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,184

per person

Jul 8 - Jul 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (365 reviews)

Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger. Location was awesome… just a couple blocks to everything!

Reviewed on May 6, 2026

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

3 out of top 10 points of interest in this area

4.5/5(229 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.

Key West Historic District

2 out of top 10 points of interest in this area

4.5/5(4,090 area reviews)

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.

Sunset Key Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$202 nightly

$227 total

May 25 - May 26

Total with taxes and fees

8.4/10 Very Good! (2,194 reviews)

An overall great experience would definitely recommend.

Reviewed on May 5, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$260 nightly

$292 total

May 10 - May 11

Total with taxes and fees

8.8/10 Excellent! (1,805 reviews)

Breakfast was great. Check in was easy. Pool was refreshing.

Reviewed on May 3, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$312 nightly

$352 total

May 26 - May 27

Total with taxes and fees

8.8/10 Excellent! (3,279 reviews)

We enjoyed our stay at Southernmost Duval guesthouse. The guesthouse was beautiful and very private and clean. We were slightly disappointed that we were so far from the resort and all the amenities. Next time we will know how to book a room at the actual resort. Thank you for your wonderful ...

Reviewed on May 5, 2026

See all 2,730 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.