1. Cheeca Lodge and Spa
© Cheeca Lodge and Spa
Location:
Islamorada, Florida KeysHighlights:
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 33036Phone: 305-712-7166
2. Southernmost Point Guest House - 3 hours 30 minutes from Miami, Florida
© Southernmost Point Guest House
Location:
Key West, FloridaHighlights:
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 33040Phone: 305-294-0715
3. Night Swan Intracoastal Bed and Breakfast - 3 hours 45 minutes from Miami, Florida
© Night Swan Intracoastal Bed and Breakfast
Location:
New Smyrna Beach, FloridaHighlights:
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 32168Phone: 386-423-4940
Romantic Weekend Getaways from Miami:
4. Palmetto Riverside Bed and Breakfast - 3 hours 30 minutes
© Palmetto Riverside Bed and Breakfast
Location:
Palmetto, FloridaHighlights:
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, FL5. Marrero's Guest Mansion - 3 hours 30 minutes from Miami, Florida
© Marrero's Guest Mansion
Location:
Key West, FloridaHighlights:
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 33040Phone: 800-459-6212
6. Hoyt House Inn - 5 hours 45 minutes
© Hoyt House Inn
Location:
Fernandina Beach, Amelia Island, FloridaHighlights:
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 32034Phone: 904-277-4300
7. The Amelia Island Williams House - 5 hours 45 minutes from Miami, Florida
© The Amelia Island Williams House
Location:
Amelia Island, FloridaHighlights:
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 32034Phone: 904-277-2328
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