- Travels By Dawn
- Apr 26
- 5 min read
Updated: May 24
IF YOU’RE PLANNING A TRIP TO KEY WEST AND WANT A STAY THAT FEELS CHIC, ICONIC, AND TRULY WORTH BOOKING, LET ME INTRODUCE YOU TO SOUTHERNMOST BEACH RESORT & GUESTHOUSES. FROM THE MOMENT YOU ARRIVE, IT HAS THAT INSTANT VACATION FEELING WITH SWAYING PALMS, OCEAN VIEWS, COLORFUL LOUNGERS, ISLAND ARCHITECTURE, AND THE KIND OF RELAXED LUXURY KEY WEST DOES SO WELL.
TUCKED AT THE QUIETER END OF DUVAL STREET, THE LOCATION IS TRULY IDEAL. YOU’RE JUST STEPS FROM THE BEST RESTAURANTS, SHOPS, AND NIGHTLIFE, WHILE STILL FEELING PEACEFUL AND PRIVATE WHEN IT’S TIME TO UNWIND. IT’S THE BEST OF KEY WEST IN ONE STAY.
WHY I LOVE STAYING HERE
THE LOCATION IS EVERYTHING
One of the best things about Southernmost Beach Resort & Guesthouses is where it’s located. Tucked at the southern end of the island, you’re steps from Southernmost Point Buoy, moments from the beach, and a beautiful walk to the energy of Duval Street. You get the fun of Key West when you want it, and a calmer, more relaxed escape when you don’t.
THE RESORT EXPERIENCE
This truly feels like a resort, which can be hard to find in Key West. It has that easy, polished vacation energy where everything feels thoughtful and elevated without ever feeling too formal. Think multiple pools, oceanfront lounging, tropical pathways, beautiful rooms, and a cocktail never far away.
THE VIEWS ARE INCREDIBLE
This is the kind of place where you want to wake up early just to enjoy the morning. The views are beautiful, the ocean breeze is perfect, and every corner has space for lingering. If you love content, photos, or just beautiful surroundings, you’ll have no shortage of moments here.
HOW I WOULD SPEND A DAY HERE
Start with a slow morning coffee walk through Old Town. Spend the afternoon by the pool or beach. Take your time exploring shops and lunch spots. Then end the day with sunset drinks before heading out for dinner or a night on Duval. It’s the kind of trip that feels easy in the best way.
IS IT WORTH IT?
Absolutely! If you only need a room to sleep in, there are other options. But if you want your hotel to feel like part of the experience, this is worth every bit of it.
The location, atmosphere, and overall experience make it one of my top choices in Key West.
BEST TIME TO BOOK
The best time to stay at Southernmost Beach Resort & Guesthouses is typically January through April when the weather is sunny, warm, and truly picture perfect. This is peak season in Key West, so rates are usually higher and rooms can book quickly.
If you’re looking for better pricing, late summer and early fall can be great options. Expect warmer temperatures and a higher chance of rain, but you may find more availability and lower nightly rates.
BEST ROOM TYPES
If your plan is to spend most of your time exploring Key West, a standard room can still be a great option while letting you prioritize budget for restaurants, activities, and sunset cocktails.
WHAT'S INCLUDED IN THE RESORT
One of the reasons this stay stands out is that it truly feels like a resort experience.
Depending on your booking, guests can enjoy:
Multiple pools
Beach access
Lounge chairs and relaxation areas
Walkable access to Key West attractions
On site dining and drinks
Beautiful tropical grounds
Easy access to sunrise and ocean views
IS IT WALKABLE?
Yes, and this is one of the biggest reasons I recommend it! Southernmost Beach Resort & Guesthouses is located at the quieter end of Duval Street, which means you can easily walk to restaurants, bars, shopping, coffee spots, and nightlife while still returning to a more peaceful area when the day is done. For Key West, walkability is everything.
PARKING & TRANSPORTATION TIPS
Parking in Key West can be limited, expensive, and honestly a hassle depending on where you stay. That’s why booking somewhere centrally located can make such a difference. Once you check in here, you may not need your car much at all. Many visitors explore by foot, bike, scooter, golf cart, or rideshare.
BEST NEARBY RESTAURANTS
One of the best parts of staying here is being close to so many iconic Key West spots. A few favorites nearby:
Blue Heaven for brunch
Louie’s Backyard for waterfront dining
Latitudes for a special occasion dinner
Southernmost Beach Cafe for oceanfront casual dining
Moon Dog Cafe for a cozy breakfast or casual lunch stop
BEST PHOTO SPOTS AT THE RESORT
If you love a beautiful backdrop, this property gives you so many moments worth capturing. My favorite spots:
Sunrise by the water
Poolside with the palms
Balcony views if your room has one
White loungers near the ocean
Walks near Southernmost Point Buoy early in the morning before crowds
HONEST PROS & CONS
PROS
Incredible location
Walkable to everything
True resort feel
Beautiful grounds and views
Great for couples, girls trips, and first time visitors
CONS
Peak season pricing can be high
Rooms in Key West can feel smaller than larger mainland resorts
Popular property, so booking early is smart
FINAL THOUGHTS
If it’s your first Key West trip and you want a stay that feels stylish, convenient, and worth the splurge, I would absolutely recommend Southernmost Beach Resort & Guesthouses. It gives you the best balance of location, atmosphere, and that classic Key West vacation feeling people come here for.
🌴 ☀️ 🌺 🌊
Our Key West trip is just getting started, and there’s so much more to share beyond our stay at Southernmost Beach Resort & Guesthouses. Be sure to follow along for my upcoming blogs on the best things to do in Key West, where to eat, and all my favorite finds!
- Travels By Dawn
GET ALL YOUR KEY WEST RESORT OUTFITS!
FAQ | IS SOUTHERNMOST BEACH RESORT & GUESTHOUSES WORTH IT?
If you value location, walkability, beautiful grounds, and a true resort feel, I would say yes. It feels like part of the vacation experience, not just a place to sleep.
FAQ | HOW FAR IS IT FROM DUVAL STREET?
It’s located at the quieter end of Duval Street, so you’re within walking distance to restaurants, bars, shopping, and nightlife.
FAQ | DOES THE RESORT HAVE BEACH ACCESS?
Yes, one of the biggest perks is having access to the beach area along with pools and oceanfront lounging spaces.
FAQ | WHEN IS THE BEST TIME TO VISIT KEY WEST?
January through April is popular for beautiful weather and sunshine. Late summer and early fall can offer better pricing.
FAQ | IS THIS A GOOD RESORT FOR COUPLES OR GIRLS TRIPS?
Absolutely. It’s a great option for couples getaways, girls trips, birthdays, and first time visits to Key West.
FAQ | DO YOU NEED A CAR IN KEY WEST?
Not necessarily. Because of the location, many visitors walk, bike, golf cart, or use rideshare during their stay.
FAQ | DO YOU RECOMMEND UBERING OR GETTING A TROLLEY PASS?
It depends on your trip style. If you plan to stay mostly in Old Town and near the resort, walking and occasional rideshare is usually enough. If you want to sightsee often and hop around multiple attractions, a Old Town Trolley Tours pass can be a fun and convenient option.
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