Southernmost Beach Resort & Guesthouses
Contemporary coastal meets Victorian history. Mid-century modern bones with updated tropical interiors throughout the main resort; the guesthouses lean into their 19th-century roots with pattern wallpaper, porch-sitting culture, and a proper B&B feel. The whole place skews social — live music, daily poolside activities, and a location that is very much on Key West's radar. Proudly LGBTQ+ welcoming.
Always book direct — the official site consistently offers 25% off that OTAs don't match
Why It Matters
It sits at America's southernmost point, literally steps from the famous buoy, which gives it a geographical bragging right most hotels can't touch. The dual-property setup is genuinely unusual: book the main resort for full beach-resort mode, or choose an adults-only Victorian guesthouse with daily breakfast and a personalized innkeeper for something closer to a boutique B&B experience — all while sharing the same six-acre amenity footprint.
At the end of Duval Street where Old Town finally runs out of road and meets the Atlantic — that's Southernmost. Open since the 1950s and spread across six acres, it operates as two distinct properties: a main beachfront resort and four intimate Victorian guesthouses (La Mer, Dewey House, Avalon, and Duval Gardens) that received a $12.5 million renovation. Four bars, three heated pools, two white sand beaches, a spa, and one oceanfront restaurant fill the space between your room and the water.
Where You'll Stay
18 room types available
Avalon King – Adults Only
Recently restored Avalon Guesthouse room. Plush king bed, flat-screen TV, bathrobes. Ground or second floor. Daily breakfast included. Tropical color palette with high colonial ceilings. Good for a romantic getaway or anniversary — the resort sells a rose petal and wine Romance Package as an add-on.
King
Avalon Two Queens – Adults Only
Recently restored Avalon main house room with high colonial-style ceilings and ceiling fans. Two queen beds, sleeps up to four. Daily breakfast included. Good for two couples traveling together.
Two QueensBoutique Guesthouse – La Mer & Dewey Ocean View King
Adults-only rooms in the lovingly restored turn-of-the-century La Mer and Dewey Houses. Victorian home atmosphere with contemporary coastal décor, king bed, vintage-inspired bathroom. Daily breakfast included on the Dewey House Deck (8am–10am). Personalized innkeeper on site.
KingBoutique Guesthouse – La Mer & Dewey Partial Ocean View Mini Suite
The best room in the La Mer / Dewey collection. Second floor, king bed, partial ocean views, private balcony, white marble bathroom. Daily breakfast on the Dewey Deck. A genuinely romantic room in a genuinely historic building.
KingDuval Gardens King – Adults Only
Recently restored Duval Gardens ground-floor king room with tropical flair. Some units open via French doors directly to the heated pool. Daily breakfast included. Lavazza coffee maker in room.
King
Duval Gardens Two Queen – Adults Only
Recently restored. Two queen beds, sleeps four. Located in the rear building on the ground floor. Floor-to-ceiling marble bathroom is the standout feature. Daily breakfast included.
Two QueensIsland View Classic King
Simple and sophisticated — a king bed, modern bathroom, island views. One of the more affordable options at the main resort without sacrificing style.
KingIsland View Classic Two Queen
Two queen beds, high-end amenities, modern bathroom. Solid choice for groups or families who don't need ocean views. Wooden floors and ceiling fans keep it feeling tropical.
Two QueensIsland View Cozy Queen
The smallest room at the resort and they say so upfront — 'the perfect Key West crashpad.' Honest assessment: cozy, stylish, fine for solo travelers or a couple who plan to be out most of the day. Don't expect to spend lazy mornings stretched out in here.
QueenIsland View Deluxe Balcony King
Old Key West spirit redesigned with upscale décor and a luxuriously dressed king bed. Private balcony with island views. One of the entry points into the Deluxe category.
KingIsland View Superior King Accessible
ADA-compliant king room near parking with a fully accessible bathroom. Conveniently located close to all resort amenities. Meets DOJ ADA Title III standards.
KingIsland View Superior Two Queen
Contemporary design, two queen beds, spacious modern bathroom. Family-friendly and one of the larger standard room footprints in the main resort. Island views rather than ocean.
Two QueensOcean Front Balcony King
The prime pick at the main resort. Directly on the Atlantic with south-facing views morning to night. The furnished balcony is the main event — you will spend time out there. Modern bathroom with herringbone tile accents.
KingOcean View King
Laid-back and elegant, with stunning ocean views without going full oceanfront price. King bed, plush linens, modern master bathroom. The views are real — not a sliver.
KingPartial Ocean View King
Simple and elegant with a king bed and serene partial ocean views. A solid mid-tier choice for couples who want an Atlantic glimpse without the oceanfront premium.
KingPartial Ocean View Two Queen Balcony
Good family option on the Atlantic side. Two queen beds, traditional Key West charm with high-end contemporary design, partial ocean views, and a balcony. Sleek modern bathroom.
Two QueensPool View Balcony King
Chic coastal décor, king bed, and a balcony looking out over the action at the pool. French doors open onto the pool area in some units. Good for guests who want to be in the thick of things.
KingThe Residence at Southernmost Beach Resort
The big one. A three-bedroom, three-bath executive residence right in the heart of the resort — about 2,000 square feet total. Full kitchen, living room, the works. Think long-stay or group travel rather than a standard hotel room. Access to all resort amenities.
Three bedroomsThe Property
Eat & Drink
5 venues on property
Restaurant
Spa & Wellness
Treatment Menu
On Property
How you'll actually spend your days.
Bicycles available for rental — a popular way to explore Key West's flat, compact streets.
Private cabana rentals poolside with full velvet-rope service. A full-day cabana rental is included with the 'Closest Cabana to Havana' package. Booking an 80-min oceanfront cabana massage also unlocks 50% off a cabana rental.
A rotating daily roster of poolside activities including tequila tastings, mojito-making sessions, sommelier training, cornhole, and live music. The entertainment calendar changes seasonally.
Regular live music performances at the Pineapple Bar and other resort venues. Schedules vary by season.
Concierge-booked jet ski rentals and excursions off Key West.
Concierge-booked snorkeling trips along America's only living reef system, located offshore from Key West.
Daily outdoor yoga sessions on the resort grounds. Part of the daily roster of fitness and wellness activities.
Two white sand beaches with priority access for resort guests. Sun loungers, umbrellas, and Atlantic swimming. The resort sits directly on South Beach, one of Key West's few actual sandy beaches.
Concierge-booked romantic sunset cruises around Key West waters.
The Pineapple Pool sits in a courtyard with manicured gardens near the lobby. The Shores Pool overlooks the Atlantic and South Beach — the social hub of the resort. The Tranquility Pool is a lush garden oasis for those wanting a quieter swim. All three are heated.
A well-groomed lawn with hammocks overlooking South Beach and the Atlantic. Part of the resort's western grounds.
Amenities & Practical Info
The details that matter for planning.
Priority beach access to South Beach with loungers and umbrellas. Swim zone accessible from the resort pier.
1,376 sq ft of event/conference space with 2 meeting rooms. 24-hour business center with computer stations. Can accommodate groups of 25–200 for indoor or outdoor events.
Free WiFi throughout the resort.
Four dedicated wedding/event venues including beachfront and private poolside options. Onsite wedding and event coordinator. Groups 25–200. Catering available.
A resort fee of approximately USD $73.13 per room per night applies. Fee inclusions should be confirmed at time of booking.
Well-equipped gym with treadmills and a range of exercise equipment. Bright, mirrored space.
Multilingual guest services staff, dedicated Key West Concierge team, bell service, fax/printer, and public computer. Maps, guides, and event calendars available.
Property explicitly welcomes guests of all sexual orientations and gender identities.
Self-parking available on-site at approximately $50/night plus taxes. EV charging station available. Parking is included in select packages (Park & Play, AAA/AARP Park & Play).
Pineapple Pool (courtyard), Shores Pool (overlooking Atlantic), and Tranquility Pool (garden oasis). Guesthouse guests also have access to private guesthouse pools.
BUILD YOUR SOUTHERNMOST BEACH RESORT & GUESTHOUSES PLAN
Rooms, dining, spa, and resort experiences — organized into one trip plan.
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