Steps to Duval St + Free Breakfast, Pool & Spa | Hotel in Key West
Hotel in Uptown - Upper Duval, Key West
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resort. This adult-focused retreat blends historic island character with full access to one of Key West’s most iconic resort experiences. Guests enjoy "stay at one, play at all" access to the full Southernmost campus, including 3 heated pools, a private beach, oceanfront bars, tropical gardens, daily activities, and a world-class spa. Walk to the Southernmost Point, step onto South Beach, or spend the day exploring Old Town before returning to a peaceful guesthouse setting designed for laid-back island living.
✨ Why Guests Love Staying Here
▶ Booking a room at The Guesthouses means enjoying an intimate boutique experience while gaining full "stay at one, play at all" access to the expansive Southernmost Beach Resort campus:
• Quiet End of Duval Street – Stay in the heart of the action but tucked away in a peaceful, sophisticated adult-focused sanctuary.
• Private Beach Access – Relax on the resort's exclusive tanning pier and private beach area with complimentary loungers.
• 3 Heated Pools – Choose your vibe between the lively Shores Pool, the tranquil Pineapple Pool, or the South Beach Pool.
• Tropical Gardens & Hammocks – Meander through award-winning lush grounds filled with hidden seating nooks and swaying hammocks.
• Daily Resort Activities – Enjoy poolside yoga, live music, and lawn games like cornhole and giant Jenga.
• Full-Service Concierge – Expert local advice for booking sunset sails, bike rentals, and the best island dining.
✨ Duval Gardens King – Historic Elegance & Spacious Comfort
▶ Nestled within the beautifully restored Duval Gardens house, the King room offers an elevated island experience. Blending historic architecture with modern beach-chic design, this room provides extra space and a grander layout for those looking to unwind in style.
▶ Sleeping Arrangements:
• 1 King Bed with a premium pillow-top mattress and high-thread-count linens.
• Sleeps up to 2 guests – A spacious and romantic retreat ideal for couples or long-term island stays.
▶ In-Room Features:
• Sophisticated Coastal Decor – Bright, airy interiors featuring local art and high-end island finishes.
• Smart Mini-Refrigerator – Perfectly sized to chill your favorite local refreshments.
• Gourmet Coffee Maker – Enjoy a fresh morning brew in the comfort of your spacious room.
• Large Flat-Screen TV – Includes premium high-definition cable and streaming options.
• High-Speed Wi-Fi – Seamless connectivity included as part of your resort stay.
• In-Room Safe, iron, and individual climate control for a personalized environment.
▶ Bathroom:
• Modern Walk-in Shower featuring custom tile work and designer fixtures.
• Signature Bath Amenities, plush towels, and a professional-grade hairdryer.
✨ A World of Food & Drink
▶ Between the Guesthouses and the main resort, you are steps away from fresh boat-to-table flavors and iconic Key West cocktails:
• Southernmost Beach Café – Oceanfront dining just 90 miles from Cuba. Enjoy a blend of Caribbean and classic Americana cuisine right on the sand.
• Shores Bar – Sip a signature Key Lime Colada while taking in stunning views of the Atlantic and South Beach.
• Pineapple Bar – A beautiful poolside retreat offering live music, house-made herb focaccia "Beach Bread," and the famous Key Lime Margarita.
• The Parlour at Avalon Guesthouse – A quaint coffee and cocktail venue. Grab a drink and head to the porch for the best people-watching on Duval Street.
• The Coffee Shop – Located by the Café, serving fresh smoothies, juices, and pastries on a lovely oceanfront patio.
✨ Unmatched Resort Amenities
▶ Your stay at The Guesthouses grants you the full luxury resort experience across the Southernmost campus:
• World-Class Spa – Indulge in ocean-side massages, facials, and signature body treatments.
• Fitness Center – Stay active with a state-of-the-art health club and weekly wellness classes.
• Tanning Pier – An iconic Key West landmark perfect for sunbathing or watching the Atlantic waves.
• Bicycle Rentals – Explore the island like a local with on-site rentals (additional fees apply).
• Lush Courtyards – Quiet, adult-friendly spaces perfect for reading or enjoying a glass of wine at sunset.
✨ Additional Details
• Check-in: 4:00 PM | Check-out: 11:00 AM.
• Must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability.
• Adult-Focused: While the main resort is family-friendly, the Guesthouses (Avalon and Duval Gardens) are designed as adult-only retreats (18+).
• Minimum Age: Must be 21+ to check in at Southernmost Beach Resort.
IMPORTANT NOTE: Guests who do not check in as scheduled will be considered a no‑show.
• Pet Policy: At this time, pets are not permitted at The Guesthouses.
• Resort Fee: A mandatory fee of $73.13 per day is required (includes Wi-Fi, fitness center access, private beach chairs/umbrellas, bottled water, and daily resort activities).
• Security Deposit: A credit card pre-authorization of your total stay plus 15% for incidentals is required at check-in.
• Housekeeping: Professional daily service is included to ensure your historic retreat remains fresh and comfortable.
• Parking: Self-parking is available for $53.75 per night. One vehicle is allowed per guestroom reservation.
• Breakfast Included: Unlike the main resort rooms, bookings at The Guesthouses typically include a daily European-style breakfast spread.
Steps to Duval St + Free Breakfast, Pool & Spa is located in Uptown - Upper Duval. Steps to Duval St + Free Breakfast, Pool & Spa provides accommodation, featuring among other amenities. This Hotel features to make your stay a comfortable one.
Steps to Duval St + Free Breakfast, Pool & Spa has 1 Bedroom , 1 Bathroom, and max occupancy of 2 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Hotel because of the excellent services rendered by the owner or manager of this Hotel, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Hotel has a friendly neighborhood, and the Uptown - Upper Duval has interesting places to visit. If you want to learn more about the Hotel in Uptown - Upper Duval, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
FAQ's
Is this Uptown - Upper Duval hotel pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Uptown - Upper Duval hotel have a swimming pool?
No, this Uptown - Upper Duval hotel does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Uptown - Upper Duval hotel?
Best-rates for the Uptown - Upper Duval hotel starts from $41,766 per night with includes with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Uptown - Upper Duval hotel a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is not considered to be a family-friendly property. As reported by the owner or manager, the hotel has not specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Uptown - Upper Duval hotel wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Uptown - Upper Duval hotel has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Uptown - Upper Duval hotel?
Based on the information reported by the owner or manager, the Uptown - Upper Duval hotel indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Uptown - Upper Duval hotel?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
