Find the Fun on Foot: A Walkable Tour of Key West's Hotels with Live Music
- nancy9487
- 4 hours ago
- 5 min read
Key West is one of the most walkable towns in the U.S. The Old Town area, where most tourist attractions are located, includes the main street, Duval Street, which stretches one mile from the Gulf of Mexico to the Atlantic Ocean. There's lots of fun to be had on Duval and its surrounding streets. If you're staying in the downtown area, there's no need for a car. Just park it, and start exploring on foot!
I love to find the hidden gems, tucked away from the main thoroughfare. Check out these walkable charming Key West hotels & inns that offer amazing entertainment and live music at their bars and pools. These fun events are not only for their guests, but open to anyone that wants to stroll by. Make an outing of it by following this fun hotel-hopping walking tour.
Key West Hotels & Inns:
Hotel-Hopping Walking Tour: Live Music & More
We will start our hotel-hopping adventure on the north side of Key West's Old Town tourist area and work our way south. This walking tour will take you to some of Key West's most beautiful hotels and inns allowing you to enjoy their stunning lush grounds and refreshing pools, whether you are a guest or not. All seven properties have a stunning setting and feel secluded, yet steps from all the action.
If you want to visit all seven properties, the walking tour is just under two miles. Or, if you would like to fully enjoy each location, I suggest you split the tour up into two days. Visit the first four properties one day and enjoy the last three hotels the next day. I've included the walking tour map below:
The Marker Key West Harbor Resort:
- Located at 200 William Street, Key West, Florida - Events Open to Public: Live music, food & drink specials, and theme nights at The Marker Starboard Poolside Bar.
The Marker Key West Harbor Resort is the perfect place to start our tour. Located in the heart of Old Town's historic seaport, it's just steps away from the bustling Duval Street. This property offers a tropical escape, with its beautiful grounds and three pools, it regularly hosts numerous events open to the public. Take a look at The Marker's Calendar of Events to find your next amazing Key West adventure.
The Key West Hotel:
- Located at 325 Duval Street, Key West, Florida
- Events Open to Public: Live music nightly and food & drink specials at The Bali Bar.
The Bali Bar, a tiki-themed bar at The Key West Hotel, is a true hidden gem! I discovered it recently and will be coming back. Situated right off of Duval Street, somehow this spot transports you to a secluded island getaway with its Balinese decor. Every evening, they offer live music and serve up island-inspired specialty cocktails. Check out their cocktail menu and sip on a fresh, fruity drink while enjoying performances by a local musician nightly.
The Saint Hotel:
- Located at 417 Eaton Street, Key West, Florida
- Events Open to Public: Live music nightly at the Halo Bar and daily happy hour specials at Burgundy Bar (4:17pm - 7:14pm)
The Saint Hotel, the oldest hotel still in operation in Key West, is an incredibly cool destination you must visit! It features a unique heaven and hell theme. On the ground floor, you will find the Tempt Restuarant with the Burgundy Bar. This spot has a dark and moody vibe with dim red lighting, a very different atmosphere from the typical Key West bar. Upstairs, the Halo Bar symbolizes heaven with its serene blue lighting. This rooftop lounge overlooks Duval Street, providing nightly live music and a chance to observe the shenanigans below. Don't miss out on their delicious themed cocktails available at both bars.
The Gardens Hotel:
- Located at 526 Angela Street, Key West, Florida
- Events Open to the Public: Jazz in the Gardens every Sunday 5pm - 7:30pm (October - May)
Hidden behind tall yellow walls, The Gardens Hotel is a tropical treasure. If you're a fan of exploring gorgeous gardens, make sure to visit the live Jazz Music Events on Sundays. This is the only day the grounds are open to the public; otherwise, they are reserved exclusively for their guests. Wander along the paths through the mini gardens, featuring quirky sculptures and a fascinating fountain. The bar and pool area are just as charming as the rest of the property.
Winslow's Bungalows:
- Located at 725 Truman Avenue, Key West, Florida
- Events Open to the Public: Daily Happy Hour Specials 4pm - 5pm
Winslow's Bungalows are a part of the Key West Historic Inns. It's another hidden away property with a lovely tropical forest atmosphere. This property is slighty off the beaten path, but worth a visit if you like a smaller, secluded bar vibe. You will follow the brick pathway through the lush foliage to the charming Bungalow Bar. Check out their daily happy hour specials for half off beverages.
La Te Da:
- Located at 1125 Duval Street, Key West, Florida
- Events Open to the Public: Numerous events including drag cabaret shows, piano bar entertainment, live music, pool parties
La Te Da is not only a historic hotel, it's also a charming entertainment hub, featuring a range of public performances. Their drag cabaret show is outstanding and truly embodies the spirit of Key West. The bar is a perfect spot to sip a drink and watch tourists stroll by on Duval Street. Every Sunday, the "One Human Family" Tea Dance is a well-loved event by the pool, offering a lively dance party with a DJ. For further information, check out La Te Da's Event Calendar.
Southernmost Beach Resort:
- Located at 1319 Duval Street, Key West, Florida - Events Open to the Public: Numerous events offered including live music on the beach, pool parties, pool games & specialty cocktails
Located on the "quieter" end of Duval Street, Southermost Beach Resort is the largest property I am featuring in this post. Offering resort amenities, this property is oceanfront, has two beaches and three pools. Most events they sponsor are open to the public and range from live music and happy hours to fun games and contests. Check out Southernmost Beach Resort's Event Calendar for more details.
Additional Attractions in Key West
Key West is a unique destination! There's so much to explore when you visit, lots of nooks and crannies. I always find exploring on foot is the best way to fully experience the local culture.
Check out these posts for other great walking tours in Key West:
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