Gay Friendly Hotels in Old Town

Island House

All-male nude resort

Times change, but Island House stays the same--this is one of the last gay clothing-optional resorts in Old Town....

1st place in Best of GayCities 2023 - Stay Gay

Old Town · 1129 Fleming St, Key West

• outdoor seating
• clothing-optional
• men-only
• LGBTQ+ owned

A clothing-optional resort for men

Located in the center of Key West's Old Town gayborhood, the Equator is just a few hops away from fabulous restaurants...

Old Town · 818 Fleming St, Key West

• clothing-optional
• men-only

Gay-owned resort in Key West's historic Old Town district

Originally built in the early 1900s and renovated in 1981, this LGBTQ-exclusive guesthouse maintains its Old Town charm...

Old Town · 1118 Fleming St, Key West

• LGBTQ+ owned

Prime sunset-facing spot between Duval St. and the Harbor Walk

Freshly renovated, the Hyatt Key West Resort and Spa includes elegant Floridian touches and luxury. It is an intimate...

Old Town · 601 Front St, Key West

• hotel

Part of a beautifully converted group of Old Town inns

The Key Lime is a 37-room historic guesthouse just two blocks from Duval Street. This former estate property is now one...

Old Town · 725 Truman Ave, Key West

• bed & breakfast
• mixed gay/straight
• hotel

Intimate escape on Key West's south shore

More sophisticated than its sister resort, Casa Marina, The Reach brings elegance and action to Old Town. Located...

Old Town · 1435 Simonton St, Key West

• hotel

Charming boutique hotel

Silver Palms has a saltwater pool for a nice and relaxing day and you can grab a drink at the pool bar. Once you feel...

Old Town · 830 Truman Ave, Key West

• mixed LGBTQ+
• hotel

Historic hotel on Duval

For those who want to be in the center of it all, La Concha anchors Duval St., the strip of bars that have made Key...

Old Town · 430 Duval St., Key West

• $$$
• $$
• hotel

Private island resort, open to public

Take the ferry from the dock on Front St. to this upscale resort. Hotel guests have access to the private beach--one...

Old Town · 245 Front Street, Key West

• $$$
• hotel

All-suite secret garden

The Santa Maria Resort is a mainstream all-suite boutique hotel with a hidden garden courtyard. Rooms include cookware...

Old Town · 1401 Simonton St, Key West

• hotel