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- The Florida Keys' Most Enchanting Places to Stay (All 26 of Them) ✨
The Florida Keys' Most Enchanting Places to Stay (All 26 of Them) ✨
From private islands to beachfront spas... your perfect Keys escape awaits...
Florida Keys Road Trip
April 10, 2025
Dear Road Trippers,
What makes a Florida Keys road trip unforgettable?
Sure, the drive is a dream—the turquoise water, the endless bridges, the wind in your hair. But where you stay? That’s where the magic settles in. It’s where memories are made with sunsets, slow mornings, and the clink of cocktails at golden hour.
This week, we’ve mapped out 26 of the most beloved, beautiful, and bucket list-worthy resorts from Key Largo to Key West. Whether you’re seeking romance, family fun, or a solo retreat, this is your official roadmap to paradise.
Grab your flip-flops. Let’s check in. 🧳✨
🌅 KEY LARGO: Gateway to Paradise
As the first island in the chain, Key Largo sets the tone for any Florida Keys adventure. It's home to crystal-clear waters, legendary diving, and some of the most luxurious and unique resorts you'll find anywhere in the state. Whether you're here to disconnect or dive deep—literally—these resorts are the perfect starting point.
🏖 Bungalows Key Largo
📍 1220 Overseas Hwy, Key Largo, FL
🌐 Website
Why You’ll Love It:
It’s the only adults-only, all-inclusive resort in the Florida Keys—and it does not disappoint. Guests are welcomed with a chilled cocktail and invited into their own stand-alone waterfront bungalow, complete with a private veranda, soaking tub, and outdoor garden shower.
Highlights:
Two oceanfront pools
Full-service spa with Himalayan salt room
Private beach with cabanas
Unlimited dining and drinks across multiple restaurants
Insider Tip:
Book a spa day and try the “Ocean Detox Ritual”—you'll come out lighter, clearer, and ready to write poetry.
🌴 Playa Largo Resort & Spa
📍 97450 Overseas Hwy, Key Largo, FL
🌐 Website
Why You’ll Love It:
This lush, 14-acre retreat is a Marriott Autograph Collection property and blends elegant, resort-style luxury with natural beauty. It’s ideal for couples, families, or anyone who wants it all—beach, spa, and adventure.
Highlights:
Sol by the Sea restaurant for dreamy waterfront dining
Family pool and kids' activities
Paddleboards, kayaks, and jet skis on-site
Ocean Spa offering marine-based therapies
Insider Tip:
Reserve a private cabana at the pool—it comes with a personal concierge and an ice bucket full of your favorite drinks.
🌿 Baker’s Cay Resort
📍 97000 Overseas Hwy, Key Largo, FL
🌐 Website
Why You’ll Love It:
Part of the Curio Collection by Hilton, this resort is tucked into a hardwood hammock forest, offering the perfect blend of luxury and eco-conscious charm. With a private beach, on-site nature trails, and guilt-free indulgence, it’s a retreat for the soul.
Highlights:
Two waterfront restaurants with sustainable menus
Daily yoga and paddleboard rentals
Dog-friendly rooms with pet welcome packages
Rooftop sunset bar with panoramic views
Insider Tip:
Book a “Baker’s Cay Sunset Room” for sweeping ocean views and front-row seats to some of the best sunsets in the Keys.
🛥 Ocean Reef Club (Members & Guests Only)
📍 35 Ocean Reef Dr, Key Largo, FL
🌐 Website
Why You’ll Love It:
If exclusivity is your vibe, this is your spot. A private, members-only community, Ocean Reef offers everything from a full marina to a private airstrip. It’s like a resort city tucked away in tropical foliage.
Highlights:
Two championship golf courses
A world-class spa and salon
Yacht club, shopping village, and multiple restaurants
Kids’ club, tennis, and diving charters
Insider Tip:
While it’s exclusive, non-members can stay through resort reservations or as a guest of a member—and it’s well worth the effort.
⚓ Reefhouse Resort & Marina
📍 103800 Overseas Hwy, Key Largo, FL
🌐 Website
Why You’ll Love It:
Part of the Opal Collection, this peaceful waterfront escape brings together all the ingredients for a classic Keys vacation: sun, sea, and serenity. It’s close to John Pennekamp Coral Reef State Park, making it a diver’s dream base camp.
Highlights:
Full marina with water excursions available
Waterfront dining and tiki bar
Bayside pool with firepits
Comfortable rooms with updated tropical décor
Insider Tip:
Book a Sunset View Room—they go fast, and for good reason. You'll watch the sky melt into the Gulf every night.
🎣 ISLAMORADA: Oceanfront Luxury Meets Laid-Back Vibes
Whether you're reeling in mahi at dawn or sipping craft cocktails at sunset, Islamorada is where your inner fisherman and your inner foodie both get exactly what they need. Here's where to stay when you want both relaxation and recreation in equal measure.
💆 Cheeca Lodge & Spa
📍 81801 Overseas Hwy, Islamorada, FL
🌐 Website
Why You’ll Love It:
Since 1946, Cheeca Lodge has been the gold standard of luxury in the Keys. With 27 acres of lush grounds, a legendary 525-foot-long fishing pier, and a full-service spa, it's an ideal blend of outdoor adventure and indulgent downtime.
Highlights:
Oceanfront tiki bar & upscale dining at Atlantic’s Edge
On-site 9-hole golf course and tennis courts
Private beach with pier-side hammocks
Full-service spa and adult-only pool
Insider Tip:
Book a Lagoon View Suite with a soaking tub on the balcony—you’ll understand the hype the second the sun sets.
🌊 The Islands of Islamorada
📍 82779 Old Hwy, Islamorada, FL
🌐 Website
Why You’ll Love It:
Imagine a private community of upscale villas, each with its own pool or rooftop terrace, nestled along a calm oceanfront shoreline. That’s The Islands. It’s perfect for group getaways, weddings, or anyone looking for space and seclusion.
Highlights:
Multi-bedroom villas with gourmet kitchens
Infinity-edge pool overlooking the Atlantic
On-site paddleboarding, snorkeling, and kayaking
Beachside firepits and tiki bar for gatherings
Insider Tip:
Check out their “Midweek Escape” packages—off-peak stays mean maximum privacy and luxury.
🐠 Islander Resort
📍 82100 Overseas Hwy, Islamorada, FL
🌐 Website
Why You’ll Love It:
This resort blends retro Floridian design with modern, eco-conscious luxury. It's spacious, family-friendly, and steps away from the best charter fishing and diving spots.
Highlights:
Multiple saltwater pools and a splash pad for kids
Beach cruiser bikes and lawn games on-site
Beachside dining at Tides Beachside Bar & Grill
Spacious suites and beach cottages with kitchens
Insider Tip:
Join their free Saturday morning yoga on the beach—followed by a mimosa, of course.
🧘 Amara Cay Resort
📍 80001 Overseas Hwy, Islamorada, FL
🌐 Website
Why You’ll Love It:
Tucked off the highway and surrounded by palm trees and hammocks, Amara Cay is Instagram-worthy, comfortable, and quietly luxurious. The resort also partners with local eco-charters and fishing guides for excursions.
Highlights:
Boutique-style rooms with modern coastal décor
Oceanfront pool, lawn games, and beach hammocks
Scooter and paddleboard rentals on-site
Great food + drinks at ReelCatch and Tiki Bar
Insider Tip:
Stay for sunset and grab their Island Old Fashioned—you’ll want to recreate it back home.
🛶 La Siesta Resort & Marina
📍 80241 Overseas Hwy, Islamorada, FL
🌐 Website
Why You’ll Love It:
Bright, beachy, and full of vintage charm, La Siesta is a fan-favorite for those who want casual, colorful comfort with easy water access. It's a short walk or bike ride from several other resorts—perfect for bar hopping or beach hopping.
Highlights:
Complimentary kayaks, paddleboards & cruiser bikes
Colorful cottages and villas for families or groups
Dockage for small boats + direct ocean access
Chill tiki bar and outdoor grilling stations
Insider Tip:
Ask for a cottage with a front porch hammock—you’ll thank us during your afternoon nap.
🐬 MARATHON: The Soul of the Florida Keys
Marathon feels like the sweet spot. You’re far enough from the hustle of Key West but close enough to explore it in a day. Here, the resorts range from laid-back hideaways to five-star stunners—and everything’s kissed by ocean breeze.
🌺 Isla Bella Beach Resort
📍 1 Knights Key Blvd, Marathon, FL
🌐 Website
Why You’ll Love It:
This place is a jaw-dropper. Sitting right at the base of the iconic Seven Mile Bridge, Isla Bella offers a sleek, luxurious escape with five pools, a private beach, and architecture that blends clean lines with coastal bliss.
Highlights:
Every room has ocean views and outdoor space
Oceanfront spa with beachside cabana treatments
On-site marina and bike rentals
Multiple bars and restaurants, including Italian fine dining
Insider Tip:
Book a spa appointment in the morning, then hop on a kayak right off the shore. It’s a sunrise-to-sunset dream.
🐚 Tranquility Bay Beachfront Resort
📍 2600 Overseas Hwy, Marathon, FL
🌐 Website
Why You’ll Love It:
The name says it all. Tranquility Bay feels like your own tropical village, with white picket fences, palm-shaded walkways, and cottages right on the sand. It's a Keys classic for families and couples alike.
Highlights:
Full-size beach houses with kitchens & porches
Adults-only pool + family pool
TJ’s Tiki Bar for cold drinks at golden hour
Butterfly Café – one of Marathon’s best restaurants
Insider Tip:
Request a beach house closest to the shoreline—you’ll watch the sun sink into the sea from your porch.
🏯 Faro Blanco Resort & Yacht Club
📍 1996 Overseas Hwy, Marathon, FL
🌐 Website
Why You’ll Love It:
A mix of nautical heritage and modern convenience, Faro Blanco is built around a historic lighthouse and includes a full-service marina—perfect for boaters and ocean lovers.
Highlights:
Historic lighthouse with killer views
Direct marina access + boating excursions
Elegant, contemporary rooms
Lighthouse Grill for delicious dockside meals
Insider Tip:
Dine by the lighthouse at sunset—it’s one of Marathon’s most underrated romantic spots.
🌾 Grassy Flats Resort & Beach Club
📍 58182 Overseas Hwy, Marathon, FL
🌐 Website
Why You’ll Love It:
Grassy Flats is a small, eco-conscious boutique resort that’s full of “Old Florida” soul. Locally owned, filled with hand-painted signs and friendly faces, it’s all about relaxation and reconnection.
Highlights:
Bohemian beach club vibes
Gorgeous pool + live music nights
Sustainability-first approach
Paddleboard-friendly shoreline and private balconies
Insider Tip:
Grab a frozen drink and sink into a hammock by the water—you’re living the Keys dream.
🐟 Hawks Cay Resort (Duck Key)
📍 61 Hawks Cay Blvd, Duck Key, FL
🌐 Website
Why You’ll Love It:
Just north of Marathon, Hawks Cay is like its own island universe. It’s built for families, anglers, and romance-seekers, and has something for every kind of traveler—plus dolphin encounters right on-site.
Highlights:
Dolphin Connection program for up-close experiences
Saltwater lagoon for kayaking and paddleboarding
Full-service spa, fitness center, and tennis courts
Villas with private pools and waterfront patios
Insider Tip:
Don’t miss the sunset cruise. It’s included in some packages and is worth every minute.
🐚 LOWER KEYS: Seclusion, Nature, and Barefoot Luxury
Just before you hit Key West, the Lower Keys give you one last taste of quiet, wild beauty. It’s where you go when you want to disconnect—and still be surrounded by absolute perfection.
🛥 Little Palm Island Resort & Spa (Little Torch Key)
📍 28500 Overseas Hwy, Little Torch Key, FL
🌐 Website
Why You’ll Love It:
This is barefoot luxury at its finest. Only reachable by boat or seaplane, Little Palm Island is adults-only, screen-free, and completely transportive. You’ll sleep in a thatched-roof bungalow, dine under the stars, and listen to the sea as your soundtrack.
Highlights:
Thatched-roof suites with ocean views and outdoor showers
A dreamy spa with sea breeze treatments
Gourmet beachfront dining with curated wine pairings
Wildlife everywhere—birds, dolphins, and the occasional manatee
Insider Tip:
Book the “Hook and Cook” package—you catch the fish, their chef cooks it to perfection.
🌇 KEY WEST: Culture, Cocktails, and Conch-Style Charm
Welcome to the end of the road! 🎉 This is where Margaritaville dreams come true, ghosts still hang out in saloons, and five-star resorts meet wild roosters and mojitos on every corner.
🛶 Sunset Key Cottages
📍 245 Front St (ferry access only)
🌐 Website
Why You’ll Love It:
A private island just off Mallory Square. The cottages are pure tropical elegance with porches, sea views, and turndown service with fresh cookies. You’re minutes from the buzz of Duval—but a world away.
Highlights:
Private beach and outdoor spa
Cottages with full kitchens and living rooms
Latitudes—one of Key West’s best fine-dining spots
Sunset ferry rides that feel straight out of a movie
Insider Tip:
Sunrise coffee on your front porch with a seabreeze is the best “room service” you’ll ever get.
🕰 Casa Marina Key West
📍 1500 Reynolds St, Key West, FL
🌐 Website
Why You’ll Love It:
A historic icon dating back to 1920, Casa Marina brings a Gatsby-era elegance to the beach. It’s grand, romantic, and home to one of the largest private beaches in Key West.
Highlights:
Historic architecture + modern luxury
Two oceanfront pools
Spa al Mare and private beach cabanas
A short walk to the Southernmost Point and Duval Street
Insider Tip:
Try the fresh coconut water served in actual coconuts—served right on the beach!
🎨 The Perry Hotel & Marina (Stock Island)
📍 7001 Shrimp Rd, Key West, FL
🌐 Website
Why You’ll Love It:
Stylish, artsy, and a favorite of locals and creatives alike. This marina-side gem offers modern rooms, cool industrial-chic decor, and one of the best brunches in town.
Highlights:
Waterfront pool with fire pits and hammocks
Dog-friendly rooms and walking trails
Three restaurants, including the top-rated Matt’s Stock Island
Access to boat charters and art galleries nearby
Insider Tip:
Wake up early and stroll the marina—you’ll spot manatees, tarpon, and an unforgettable sunrise.
🌅 Ocean Key Resort & Spa
📍 Zero Duval St, Key West, FL
🌐 Website
Why You’ll Love It:
Location, location, location. This luxe escape is at the literal corner of the island—Zero Duval Street—where Key West sunsets steal the show every evening.
Highlights:
All rooms face the ocean or Mallory Square
SpaTerre with couples’ treatments overlooking the sea
Sunset Pier—great drinks, music, and THAT view
Walk out your door and you’re at Mallory Square
Insider Tip:
Book a spa appointment right before sunset—you’ll float into happy hour like royalty.
🌼 The Marquesa Hotel
📍 600 Fleming St, Key West, FL
🌐 Website
Why You’ll Love It:
A boutique favorite tucked just off Duval, this charming 1880s conch house-turned-hotel is peaceful, elegant, and full of heart.
Highlights:
Award-winning Café Marquesa
Garden courtyards and quiet pools
Timeless rooms with four-poster beds and antiques
Adults-only serenity just steps from the fun
Insider Tip:
Ideal for honeymoons or introverts seeking sanctuary with a side of luxury.
⚓ The Reach Key West
📍 1435 Simonton St, Key West, FL
🌐 Website
Why You’ll Love It:
Stylish and central, The Reach boasts one of the only natural beaches in Key West. It’s walkable, waterfront, and the epitome of easy luxury.
Highlights:
Modern, bright rooms with balconies
Hammocks on the sand and beachside service
Easy access to all the Old Town action
Great sunset dining at Four Marlins
Insider Tip:
Grab a paddleboard or snorkel gear from the beach shack—it’s included.
🦜 Parrot Key Hotel & Villas
📍 2801 N Roosevelt Blvd, Key West, FL
🌐 Website
Why You’ll Love It:
Tropical, tranquil, and just far enough off Duval for peace. Parrot Key’s villas offer privacy, bright design, and lush garden paths.
Highlights:
Four pools, spacious villas
Shuttle to downtown and Smathers Beach
Kayaking and paddleboarding on the bay
Peaceful escape with palm-fringed courtyards
Insider Tip:
Perfect for families or longer stays when you want both space and serenity.
📍 Southernmost Beach Resort
📍 1319 Duval St, Key West, FL
🌐 Website
Why You’ll Love It:
A beachfront resort that captures both elegance and accessibility. Just steps from the iconic Southernmost Point and walking distance to Old Town’s buzz.
Highlights:
Three pools + private beach access
Oceanfront bar and restaurant
Gorgeous photo ops everywhere
Top-notch hospitality
Insider Tip:
Reserve a poolside cabana and sip a mojito while you plan your next adventure.
🏝 Hyatt Centric Key West
📍 601 Front St, Key West, FL
🌐 Website
Why You’ll Love It:
Close to the action but tucked away enough to feel like a retreat, this is Hyatt quality with island charm—plus one of the best locations for cruise-watchers and sunset chasers.
Highlights:
Seaside spa and outdoor dining
Walk to Mallory Square and Duval
Balconies with harbor views
Full-service marina nearby
Insider Tip:
Ask for a room with a west-facing balcony—you’ll catch the fireworks every night (aka the sunset).
🛥 Opal Key Resort & Marina
📍 245 Front St, Key West, FL
🌐 Website
Why You’ll Love It:
Steps from Mallory Square, this polished resort gives you front-row seats to the nightly celebration of sun and sea. It’s modern, lively, and just upscale enough.
Highlights:
Marina-side dining and cocktail lounge
Heated pool, whirlpool, and waterfront views
Luxury rooms with tropical décor
One of the best sunset-watching spots in town
Insider Tip:
Head to the Sunset Deck for the view, stay for the margaritas.
📥 Ready to Book?
We’ve put all 26 resorts into a beautifully designed, downloadable PDF guide—perfect for planning, sharing, or stashing away for your next spontaneous escape.
👉 Click here to download the guide.
💬 What’s Your Favorite Resort in the Keys?
Reply to this email and let us know—we might feature your favorite in next week’s newsletter!
Until next time, may your towel always be dry and your cocktail always cold,
Brian
Florida Keys Road Trip Team
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