Weekend Getaways from Miami
I found weekend getaways from Miami to be wonderfully varied. In just a short drive, you can escape the bustle of the city and find yourself in tropical islands, quiet beach towns, lush wetlands, or even vibrant cultural hubs. One of the best parts is picking a unique resort, boutique hotel, or seaside inn to serve as your retreat while you explore. Here are some standout accommodations I discovered that make the perfect base for a memorable South Florida weekend escape.
1. Relaxing at Cheeca Lodge & Spa
There’s a timeless magic to the Florida Keys, and Cheeca Lodge & Spa in Islamorada captures it perfectly.
This luxury resort has long been considered one of the most romantic escapes in the Keys, blending tropical beauty with elegant comfort.
We drove about an hour and 45 minutes south from Miami along the Overseas Highway to Islamorada.
After a two-and-a-half hour trip from Miami, there’s something about the Keys that always makes me breathe a little deeper. I found Cheeca Lodge in Islamorada to be the best version of that fact.
My suite for two days combined comfort and elegance, with coastal-inspired décor, plush bedding, and a balcony that overlooked the Atlantic. It featured oversized windows, a marble bathroom with a soaking tub, a rain shower, and tropical art pieces that added a sense of place. The thoughtful touches—like a curated minibar, Nespresso machine, and signature bath amenities—made the stay feel extra indulgent.
Cheeca’s dining options were another highlight. From fresh seafood enjoyed right on the beach to cocktails sipped while watching the sun sink below the horizon, every meal felt like part of the experience.
The resort also offers plenty of activities: fishing off the famous pier, kayaking through calm waters, playing a round on the golf course, or simply lounging by one of the pools with a tropical drink in hand.
Of course, the spa was a must for me. With treatments inspired by the sea and a serene setting, it was the perfect way to recharge after a day in the sun.
For me, Cheeca Lodge & Spa is more than just a resort. It’s a romantic, tropical sanctuary where every moment feels unforgettable.
To book, check availability or prices for Cheeca Lodge.
What I loved best:
I loved the private balconies, soaking tubs, and island-inspired décor that made my space feel both luxurious and laid-back.
2. Staying at Southernmost Point Guest House - 3 hours 30 minutes from Miami, Florida
Tucked just steps from the famous buoy in Key West, Southernmost Point Guest House felt like stepping into a postcard, but one with quiet corners and gracious hosts. The gardens were lush, the wraparound porches wide, and the whole property hummed with old Key West charm.
Perched right on iconic Duval Street and just steps from the ocean, the Southernmost Point Guest House is a charming escape that blends historic Key West character with tropical ease.
We drove about four hours south from Miami, following the Overseas Highway all the way down to Key West.
Housed in a beautifully preserved Victorian mansion, this guest house feels worlds away from the bustle, even though you’re in the heart of everything.
I was drawn to the wide front porch shaded by palms and the warm, welcoming atmosphere that made me feel instantly at home.
Each guest room is unique, with a mix of antique furnishings, colorful island décor, and modern comforts.
I loved how my room for two nights had both vintage charm and thoughtful touches, plush bedding, cool tile floors, and a balcony perfect for sipping morning coffee while soaking up the sea breeze. Some rooms even offer ocean views, which quickly became my favorite feature.
Breakfast each morning was a highlight for me, with fresh tropical fruit and homemade treats served on the veranda, it set the perfect tone for the day.
The location couldn’t be better. I could stroll to the Southernmost Point buoy in minutes, wander through historic neighborhoods, or head right into the vibrant shops, bars, and restaurants along Duval Street.
For me, the Southernmost Point Guest House is a true Key West gem, romantic, historic, and wonderfully relaxed, with the best of the island right at your doorstep.
To book, check availability or prices for Southernmost Point Guest House.
What I loved best:
The guest house also has a lovely outdoor pool surrounded by lush gardens, making it easy to relax between exploring Key West’s lively streets.
3. Waking Up at Night Swan Intracoastal Bed and Breakfast - 3 hours 45 minutes from Miami, Florida
Sitting gracefully along the Indian River, the Night Swan Intracoastal Bed and Breakfast is the kind of place that makes you feel instantly at peace.
This charming inn, set in two beautifully restored 1900s homes, combines the warmth of a traditional bed and breakfast with the breezy, coastal spirit of Florida.
When I walked up to the wraparound porch and caught sight of the sailboats drifting by, I knew this was a hidden gem perfect for a romantic escape.
My oom for two days was cozy, welcoming, and full of personality. I loved the blend of antique furnishings and modern touches, plush beds, hardwood floors, and large windows that framed stunning water views.
Breakfast at the Night Swan was another highlight. Served on the porch or in the sunny dining room, each meal was hearty and homemade, with fresh flavors that started the day perfectly.
The innkeepers were warm and attentive, always ready with insider tips on the best local restaurants, hidden beaches, and things to do around town.
The location is ideal, close to New Smyrna’s lively downtown, yet tucked away enough to feel serene and private. Whether kayaking on the river, strolling the beach, or simply unwinding on the porch, every moment here felt restorative.
For me, the Night Swan Intracoastal B&B is a true Florida treasure, romantic, welcoming, unforgettable, and one of the best weekend getaways from Miami.
To book, check availability or prices for Night Swan .
What I loved best:
My favorite detail was the private balcony, where I could sit with a glass of wine at sunset and watch dolphins play in the river. It felt magical and deeply personal.
4. Escaping to Marrero’s Guest Mansion - 3 hours 30 minutes from Miami, Florida
Stepping into Marrero’s Guest Mansion feels like entering a piece of Key West history. Built in 1889 by cigar baron Francisco Marrero, this Victorian mansion turned boutique inn blends old-world romance with island charm.
Just a block from Duval Street, it offers the perfect mix of lively access and tranquil retreat.
I was enchanted by the grand wraparound porch, lush tropical gardens, and the warm welcome that instantly made me feel like part of the home’s story.
The rooms are unique and full of character, each decorated with a thoughtful blend of antique furnishings and modern comfort.
My room had soaring ceilings, hardwood floors, and a private balcony shaded by palms. The vintage charm, paired with plush linens and updated amenities, created a stay that felt both timeless and indulgent.
The location is unbeatable! You’re within easy walking distance of the Southernmost Point, Mallory Square’s famous sunsets, and all the restaurants, bars, and shops Duval Street has to offer.
Yet, back at the mansion, it feels quiet, romantic, and private. For me, Marrero’s Guest Mansion is a Key West treasure, historic, intimate, and wonderfully romantic.
To book, check availability or prices for Marrero’s Guest Mansion .
What I loved best:
Breakfast at Marrero’s was a highlight for me. Enjoyed on the veranda, it included fresh fruit, baked goods, and coffee brewed just right to sip while watching the town slowly wake up.
The inn also has a lovely pool tucked into the garden, perfect for cooling off after a day of exploring Key West’s colorful streets.
5. Feeling at Home at Hoyt House Inn - 5 hours 45 minutes
The Hoyt House Inn in Fernandina Beach is the kind of place that makes you fall in love with both its history and its charm.
We drove about 40 minutes northeast from Jacksonville to Fernandina Beach on Amelia Island.
Hoyt House in Fernandina Beach felt like the kind of place where you arrive as a guest and leave as part of the story.
The Victorian mansion was full of charm, from the hand, carved staircase to the peaceful back garden, and the innkeepers had this way of knowing just when to chat and when to let you be.
Built in 1905, this Queen Anne–style mansion has been beautifully restored into an intimate bed and breakfast that feels grand yet inviting.
Set beneath a canopy of moss-draped oaks and just steps from the shops and restaurants of historic downtown, it’s one of my favorite romantic escapes in Florida.
I was struck by the wraparound porch, stained glass windows, and the sense of timeless elegance that flows through the house.
Inside, each of the guest rooms is unique, with high ceilings, antique furnishings, and plenty of character.
My room for two days had a plush four-poster bed, elegant drapery, and a clawfoot tub, details that made me feel both pampered and transported to another era.
It was the perfect blend of vintage style and modern comfort.
Later in the day, relaxing by the inn’s saltwater pool or sipping a cocktail in the parlor felt like indulgent little luxuries.
The location is ideal. You can walk to Amelia Island’s charming downtown or take a short drive to the beach.
For me, the Hoyt House Inn is a true hidden gem, romantic, historic, and wonderfully welcoming, making it an unforgettable Florida getaway.
To book, check availability or prices for Hoyt House .
What I loved best:
Breakfast at the inn was one of my favorite highlights. Served in a bright dining room, the menu included homemade pastries, seasonal fruit, and hearty Southern classics that started each morning on a delicious note.
Why These Places Stay With Me:
Each of these getaways gave me more than rest, they gave me moments I didn’t expect. A peaceful porch swing at sunset, breakfast on a quiet veranda, or the way ocean air softens everything. These are the kind of weekends that fill you up in all the right ways.
My personal highlights:
Some of my favorite Miami weekend getaways include Key West for its sunsets and island energy, Naples for its unique Gulf Coast charm, and the underrated Everglades for its wildlife and airboat adventures. Each one delivers the best mix of scenery, culture, and fun.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
