Duval Street Stay
+ Free Breakfast, Beach & Pool

The boutique experience with full resort access.

Picture a historic guesthouse at the quiet end of Duval Street, then hand yourself the run of a full oceanfront resort. That's The Guesthouses at Southernmost Beach Resort — one of Key West's better-kept secrets. You get an intimate, refined stay in a restored home dating back well over a century, with the whole Southernmost campus at your fingertips.

Three resort pools. Private beach and a tanning pier. Oceanfront restaurants and bars, tropical gardens, hammocks, daily activities, a spa, and a fitness center — all part of the stay. And here's the part people love: the Guesthouses are adults-only, so it stays peaceful and grown-up, no kids doing cannonballs beside your lounge chair. Note the age minimum runs higher than a typical resort, so confirm the current cutoff when you book.

You're a minute or two from South Beach and the Southernmost Point, a couple minutes from Duval nightlife, and roughly a 10-to-15-minute hop from the airport. About as convenient as the island gets.

The Room — Avalon Petite Queen

You're staying in the restored Avalon, the guesthouse's historic 1885 home. This room leans into upscale island charm in a compact, efficient layout — old-Key-West bones, modern coastal finishes, everything you need for a refined home base.

• Queen bed with premium pillow-top mattress and high-thread-count linens
• Modern walk-in shower with designer tile and strong water pressure
• Smart mini-fridge, gourmet coffee maker, flat-screen TV with streaming
• High-speed Wi-Fi, in-room safe, iron, individual climate control
• Private balcony

Resort Amenities (All Included)

Dining & Bars on Campus

• Southernmost Beach Café — Oceanfront dining with Caribbean-meets-Americana plates right on the sand
• Shores Bar — Casual bites and cold drinks looking out over the Atlantic and South Beach
• Pineapple Bar — Poolside, live music, and the resort's signature Key Lime Margarita
• The Coffee Shop — Next to the café for morning coffee, smoothies, and pastries before you hit the beach

Location

Good to Know

• Adults-only — there's an age minimum to check in, and it runs higher than most resorts, so confirm the current cutoff
• Check-in mid-afternoon, check-out late morning (roughly 4 PM / 11 AM — verify at booking)
• Expect a daily resort fee (somewhere around $70/day last we checked) covering Wi-Fi, beach chairs, fitness center, bottled water, and daily activities
• Self-parking runs extra — figure roughly $50/night
• No pets at the Guesthouses
• Daily housekeeping is included

Book the room, then let the sunset sail, the dinner reservation, and the snorkel trip line up themselves — let togu.ai plan the rest of your stay →

Key West changes fast — prices, hours, and openings shift. Always double-check before you go, or let togu.ai handle it for you.