Name: Winslow's Bungalows - Key West Historic Inns
Price range: €239
Rating: 9

Popular places to visit

Southernmost Point

4/5(39 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

South Beach

4.5/5(8 reviews)

The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

Ernest Hemingway Home and Museum

4.5/5(23 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Higgs Beach which includes a beach and tropical scenes as well as a large group of people

Clarence S. Higgs Memorial Beach Park

4/5(11 reviews)

Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.

Harry S. Truman Little White House

4.5/5(12 reviews)

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Key West Butterfly and Nature Conservatory

4.5/5(10 reviews)

With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.

Things to do

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

€86

per adult

74% of travellers recommend

MIAMI: Key West Day Trip with Boating Options

€86

per adult

Shark and Wildlife Viewing Adventure in Key West

€86

per adult

100% of travellers recommend

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

€47

per adult

84% of travellers recommend

The Dark Side of Key West Adults Only Walking Tour

€30

per adult

80% of travellers recommend

Key West Jet Ski Tour – High-Speed Adventure Around the Island

Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!

€147

per traveller

94% of travellers recommend

See all activities in Key West

Top hotels in Old Town Key West

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

€228

2 Sept - 3 Sept

includes taxes & fees

Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...

8.6/10 Excellent! (2,680 reviews)

"We enjoyed our stay at Southernmost resort. Our room in the Atlantic building was quiet, clean and had a nice view of the ocean. Lots of spaces to lounge throughout property, including a pier, three pools, spa and good restaurant. Loved location. Easy to book bikes, golf cart or excursions. We would ..."

Reviewed on 17 Aug 2025

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL

€257

27 Aug - 28 Aug

includes taxes & fees

Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...

8.2/10 Very Good! (300 reviews)

"The staff and service is exemplary. Ask for Nicole and Marsha at the Dorada beach bar. Both are awesome bartenders and great people!!!"

Reviewed on 19 Aug 2025

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street, Key West, FL

Fully refundableReserve now, pay when you stay

€268

15 Sept - 16 Sept

includes taxes & fees

Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...

8.4/10 Very Good! (1,003 reviews)

Tropical paradise within your Reach

"Staff friendly and so accommodating! My wife somewhat particular about view from room; Phiwe and her colleague guided us to the perfect room overlooking pool and, a few feet beyond, the sandy beach. Lots of extras and you are able to walk over to sister property Casa Marina and hang out there too. ..."

Reviewed on 10 Aug 2025

The Southernmost Inn - Adults Only

525 United Street, Key West, FL

€134

21 Aug - 22 Aug

includes taxes & fees

Stay at this 3-star hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...

8.2/10 Very Good! (1,161 reviews)

"Ok"

Reviewed on 16 Aug 2025

Southwinds Motel

1321 Simonton Street, Key West, FL

€145

2 Sept - 3 Sept

includes taxes & fees

Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...

8.6/10 Excellent! (1,156 reviews)

"Staff was very nice and proficient. Allowed me to check in early that was much appreciated!"

Reviewed on 16 Aug 2025

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue, Key West, FL

€239

21 Aug - 22 Aug

includes taxes & fees

Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular ...

9/10 Wonderful! (1,006 reviews)

"The staff is amazing! They always go above and beyond getting fast results if you need an item, need a recommendation, etc. Keep coming back year and year!"

Reviewed on 18 Aug 2025

See all 1,326 properties in Old Town Key West

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.

Other neighbourhoods around Old Town Key West

Key West Butterfly and Nature Conservatory featuring animals, flowers and zoo animals

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Key West Butterfly and Nature Conservatory are top sights worth seeing.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Key West Historic District

4.5/5(66 area reviews)

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Saint Mary Star of the Sea.

Harry S. Truman Little White House showing a house and cycling

Bahama Village

5/5(1 area review)

Bahama Village is noteworthy for its historical sites, and you can make a stop at top attractions like Duval Street and Key West Lighthouse and Keeper's Quarters Museum.

Casa Marina

While visiting Casa Marina, you might make a stop by sights like Clarence S. Higgs Memorial Beach Park and Florida Keys Beaches.

White St. Gallery

If you're looking for some top things to see and do in White St. Gallery and surrounding area, you can visit Duval Street and Saint Mary Star of the Sea.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Old Town Key West

Key West

Visit Old Town Key West

Popular places to visit

Southernmost Point

South Beach

Ernest Hemingway Home and Museum

Clarence S. Higgs Memorial Beach Park

Harry S. Truman Little White House

Key West Butterfly and Nature Conservatory

Things to do

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

MIAMI: Key West Day Trip with Boating Options

Shark and Wildlife Viewing Adventure in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

The Dark Side of Key West Adults Only Walking Tour

Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!

Top hotels in Old Town Key West

Southernmost Beach Resort and Guesthouses

Casa Marina Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

The Southernmost Inn - Adults Only

Southwinds Motel

Winslow's Bungalows - Key West Historic Inns

Check Old Town Key West hotel availability

Other neighbourhoods around Old Town Key West

Uptown - Upper Duval

Downtown Key West

Key West Historic District

Bahama Village

Casa Marina

White St. Gallery

Hotels Near Old Town Key West, Key West

Old Town Key West

Travellers

Room 1