In This Article

1. Cheeca Lodge and Spa

Cheeca Lodge and Spa

© Cheeca Lodge and Spa

Location:

Islamorada, Florida Keys

Highlights:

If you’re craving barefoot luxury with an island breeze, Cheeca Lodge and Spa is a tropical dream come true. Hidden in lush greenery in the Florida Keys, this laidback oceanfront haven wraps you in sun, sand, and stress-melting comfort.

Recommended For:

Couples, families, spa lovers, beachgoers, and anyone looking for a luxe-yet-easygoing Florida Keys escape.

What I Love:

Island-inspired suites, a private beach, endless water activities, on-site golf, and a tranquil spa oasis.
  • Unwind in spacious, island-themed rooms or suites—some with full kitchens, soaking tubs, rainfall showers, and pull-out sofas.
  • Play all day with access to watersports, a fishing pier, six tennis courts, two pools, a kids' center, and a nine-hole golf course.
  • Recharge at the full-service spa or break a sweat in the modern fitness center before lounging beachside under swaying palms.
  • Dine at several on-site restaurants offering fresh seafood and tropical flavors in a relaxed coastal setting.
  • Explore nearby nature—Windley Fossil Reef Geological State Park is just 5 miles away and offers a fascinating glimpse into the island’s ancient coral past.

Address:

81801 Overseas Hwy, Islamorada, FL 33036
Phone: 305-712-7166

2. Southernmost Point Guest House - 3 hours 30 minutes from Miami, Florida

Southernmost Point Guest House -  3 hours 30 minutes from Miami, Florida

© Southernmost Point Guest House

Location:

Key West, Florida

Highlights:

If you want to stay somewhere with Old Key West charm and tropical tranquility, Southernmost Point Guest House is your spot. This Queen Anne-style Victorian beauty on lively Duval Street offers both peaceful garden vibes and unbeatable location.

Recommended For:

Couples, solo travelers, garden lovers, architecture enthusiasts, and anyone wanting to blend comfort with Key West culture.

What I Love:

Elegant 1894 architecture, tropical gardens with hammocks, homey suites with modern perks, and hot breakfast on a breezy veranda.
  • Stay in one of ten charming rooms or suites with private baths, flat-screen TVs, air conditioning, Wi-Fi, refrigerators, and coffee makers.
  • Relax in shaded hammocks or cool off in the peaceful garden-side swimming pool after exploring the island.
  • Indulge in hot breakfast served daily on the porch—an ideal start to a lazy Key West morning.
  • Upgrade with suites that feature full kitchens, oceanview balconies, living areas, or private porches.
  • Explore nearby attractions like the Key West Butterfly & Nature Conservatory, located just steps away.

Address:

1327 Duval St, Key West, FL 33040
Phone: 305-294-0715

3. Night Swan Intracoastal Bed and Breakfast - 3 hours 45 minutes from Miami, Florida

Night Swan Intracoastal Bed and Breakfast - 3 hours 45 minutes from Miami, Florida

© Night Swan Intracoastal Bed and Breakfast

Location:

New Smyrna Beach, Florida

Highlights:

Looking for a peaceful waterfront escape with Old Florida charm? Night Swan Intracoastal Bed and Breakfast offers front-row views of passing boats, relaxing porches, and romantic vibes in a pair of historic homes and a cozy cottage.

Recommended For:

Couples, boaters, pet lovers, and anyone looking for a romantic, laidback getaway by the water.

What I Love:

Sweeping views of the Intracoastal Waterway, a private boat dock, whirlpool tubs, and pet-friendly charm in a historic setting.
  • Stay in one of 16 inviting rooms with private bathrooms, free Wi-Fi, and character-rich décor—some with water views, whirlpool tubs, four-poster beds, or kitchenettes.
  • Relax on the large porch, veranda, or lawn while watching boats drift past the shoreline.
  • Bring your boat—guests enjoy complimentary docking at the inn’s private dock.
  • Dine on a hot, homemade breakfast served each morning in the main house.
  • Explore nearby attractions like the beach (2.3 miles away) and Smyrna Dunes Park (4.2 miles), or bring your pup to one of the pet-friendly rooms.

Address:

512 S Riverside Dr, New Smyrna Beach, FL 32168
Phone: 386-423-4940

Romantic Weekend Getaways from Miami:

4. Palmetto Riverside Bed and Breakfast - 3 hours 30 minutes

Palmetto Riverside Bed and Breakfast - 3 hours 30 minutes

© Palmetto Riverside Bed and Breakfast

Location:

Palmetto, Florida

Highlights:

Dreaming of a historic waterfront stay with easy access to Florida’s Gulf Coast gems? Palmetto Riverside Bed and Breakfast is a beautifully preserved 1913 home where river views, antique charm, and warm hospitality come together in a peaceful, elegant setting.

Recommended For:

Couples, history buffs, beachgoers, and travelers seeking a romantic, well-located getaway with classic Southern charm.

What I Love:

Antique-filled rooms, water views, a 200-foot private pier, and gourmet breakfasts overlooking the marina.
  • Stay in one of six thoughtfully appointed rooms or suites, each with private bathrooms, flat-screen TVs, free Wi-Fi, and charming antique furnishings.
  • Relax on the 200-foot pier or enjoy peaceful water views from select guest rooms.
  • Dine on a hot gourmet breakfast served in the screened Florida Room, with a serene view of Regatta Point Marina.
  • Explore nearby beach towns and cities—Anna Maria Island, Bradenton, Sarasota, St. Pete, and Tampa are all within easy reach.
  • Admire the historic ambiance of this National Register-listed 1913 mansion in the heart of Palmetto village.

Address:

Palmetto Riverside Bed and Breakfast, Palmetto, FL

5. Marrero's Guest Mansion - 3 hours 30 minutes from Miami, Florida

Marrero's Guest Mansion - 3 hours 30 minutes from Miami, Florida

© Marrero's Guest Mansion

Location:

Key West, Florida

Highlights:

If you love a stay with a story, Marrero’s Guest Mansion is a historic gem that blends Victorian charm with modern comfort. Built in 1889 by a cigar baron, this elegant retreat offers quiet luxury just steps from Duval Street.

Recommended For:

History lovers, romantic couples, architecture fans, and travelers wanting to be close to the Key West buzz without giving up serenity.

What I Love:

Gorgeous original architecture, lush gardens, a heated pool, daily Happy Hour, and a veranda perfect for Key West people-watching.
  • Stay in beautifully restored, non-smoking rooms with refrigerators, cable TV, and air conditioning—each with its own unique layout and charm.
  • Unwind in the tropical garden setting, take a dip in the heated pool, or rinse off under the outdoor shower.
  • Start your day with an expanded continental breakfast and enjoy the relaxed vibe of the daily Happy Hour.
  • Relax on the front veranda with a cocktail and enjoy the lively hum of nearby Duval Street just a block away.
  • Convenient off-street parking makes exploring the island by foot or bike even easier.

Address:

Marrero's Guest Mansion, 410 Fleming Street, Key West, FL 33040
Phone: 800-459-6212

6. Hoyt House Inn - 5 hours 45 minutes

Hoyt House Inn - 5 hours 45 minutes

© Hoyt House Inn

Location:

Fernandina Beach, Amelia Island, Florida

Highlights:

If you're looking for charm, comfort, and a touch of Southern elegance, Hoyt House Inn is the perfect pick. This 110-year-old plantation-style beauty sits right in Fernandina Beach’s Historic District, surrounded by coastal charm and walkable delights.

Recommended For:

Romantic getaways, history buffs, antique lovers, and travelers wanting a relaxed, boutique stay near the beach.

What I Love:

Unique 1900s décor in every room, plush robes and terry wraps, and sweet touches like fresh-baked cookies and complimentary bottled water.
  • Stay in one of ten individually decorated rooms with private baths, heat and A/C control, and king or queen-sized beds.
  • Enjoy thoughtful amenities like robes, toiletries, fresh-baked cookies, and bottled water—offered no matter which room you choose.
  • Explore the vibrant neighborhood just outside your door—filled with shops, galleries, and local restaurants in a charming seaside village.

Address:

804 Atlantic Ave, Fernandina Beach, FL 32034
Phone: 904-277-4300

7. The Amelia Island Williams House - 5 hours 45 minutes from Miami, Florida

The Amelia Island Williams House - 5 hours 45 minutes from Miami, Florida

© The Amelia Island Williams House

Location:

Amelia Island, Florida

Highlights:

If you love historic charm paired with thoughtful luxury, The Amelia Island Williams House is a true Southern treasure. Set across two antebellum mansions and a charming carriage house, this elegant inn invites you to slow down and savor timeless hospitality.

Recommended For:

History lovers, romantic couples, foodies, and anyone seeking a refined yet welcoming getaway on the Florida coast.

What I Love:

Stay in 19th-century mansions, enjoy gourmet two-course breakfasts, and relax in beautifully appointed rooms with luxury linens and period charm.
  • Choose from 11 rooms spread across three buildings: the historic Williams House, the Hearthstone House, or the newer Carriage House built in 2003.
  • Rest easy with king or queen beds, private bathrooms, and custom linens in every room—perfect for a pampered night's sleep.
  • Start your day with a two-course gourmet breakfast featuring fruit, baked goods, and savory delights like blueberry stuffed French toast or asparagus bacon quiche.

Address:

103 S. 9th St., Amelia Island, FL 32034
Phone: 904-277-2328

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