Gay Key West FL, Gay Friendly Vacation Rentals, Guest Houses, Resorts

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Gay Friendly Accommodations in Key West, Florida

Vacation rentals are an extremely popular type accommodation in Key West. Often apartment, condos, suites, or cottages/homes, these rentals provide guest with slight more privacy, and a more local feel to your stay.


Andrews Inn & Garden Cottages
Location: Key West
Type: Resort  Size: 10 Unit/Room(s)
Starting at: Call for Rates
To reach this charming bed and breakfast, you wander down a shaded lane steps from Duval Street. Andrews Inn immediately offers peace and tranquility as you enter through a garden gate to our secluded world. A shimmering pool is nestled in a lush t...read more »
Truman Annex
Location: Key West
Type: Vacation Home - 4 Bedroom(s) 4.0 Bath  Sleeps: 8
Starting at: $5,500.00/Wk
This home has everything to offer from exotic furnishings and accessories to a 40 foot private pool! Located in the heart of Old Town within the Truman Annex this home is convieniently located within walking distance to all of the area attractions an...read more »
Truman Annex Private Estate
Location: Key West
Type: Vacation Home - 4 Bedroom(s) 4.0 Bath  Sleeps: 8
Starting at: $5,500.00/Wk
Luxury 4BR home in the heart of Old Towns Truman Annex. Fully appointed with gourmet kitchen and private pool....read more »
Bay Pointe
Location: Key West
Type: Vacation Home - 3 Bedroom(s) 3.0 Bath  Sleeps: 8
Starting at: $4,200.00/Mo
Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom. The second floor h...read more »
Historic Key West Inns
Location: Key West
Type: Resort  Size: 115 Unit/Room(s)
Starting at: Call for Rates
Historic Key West Inns are comprised of 6 unique and historic inns that are conveniently located next to all the Duval Street and Old Town action. Each inn has its own charm and accommodations to suit all your vacation needs. Every morning begins wit...read more »
Location: Key West
Type: Condo - 2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,600.00/Wk
The Best of Key West gets even better! Beachside Resort & Conference Center is a seven acre luxury waterfront resort condominium with lush tropical gardens, large waterfront swimming pool, Jacuzzi, resting canopies, two bars and a fine restaurant. Yo...read more »
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