Escape to Paradise: 10 Iconic Resorts in the Florida Keys 🌴✨

Dear Road Trippers,

If you’re planning a Florida Keys getaway, finding the perfect place to stay can make all the difference. Whether you’re looking for waterfront luxury, a boutique escape, or a relaxing tropical hideaway, the Keys have it all. This week, we’re highlighting the top 10 resorts from Key Largo to Key West—each offering its own unique charm and unforgettable views.

Pack your bags and let’s dive into paradise!

1. Playa Largo Resort & Spa (Key Largo)

📍 Location: 97450 Overseas Hwy, Key Largo, FL
🌐 Website: Playa Largo Resort & Spa

Why It’s a Must-Stay:
Nestled on 14 beachfront acres, Playa Largo is the epitome of modern luxury in Key Largo. Relax by the infinity pool, indulge in a treatment at the Ocean Spa, or sip cocktails at the Sol by the Sea beachfront restaurant. Perfect for couples and families alike.

👉 Pro Tip: Don’t miss the nightly beachside fire pits—an ideal way to unwind under the stars.

2. Baker’s Cay Resort (Key Largo)

📍 Location: 97000 Overseas Hwy, Key Largo, FL
🌐 Website: Baker’s Cay Resort

Why It’s a Must-Stay:
Tucked into a lush tropical forest, this eco-friendly resort is known for its stunning private beach and incredible sunset views. With two on-site restaurants and plenty of water activities like kayaking and paddleboarding, Baker’s Cay is an adventurer’s dream.

👉 Pro Tip: Try the Key Lime Pie Martini at the tiki bar—it’s legendary!

3. Cheeca Lodge & Spa (Islamorada)

📍 Location: 81801 Overseas Hwy, Islamorada, FL
🌐 Website: cheeca.com

Why It’s a Must-Stay:
Known as the “Crown Jewel of Islamorada,” Cheeca Lodge offers a mix of casual elegance and outdoor adventure. Spend your days fishing, snorkeling, or golfing, and then relax at the adults-only pool or the full-service spa.

👉 Pro Tip: Book one of the oceanfront bungalows for your own private slice of paradise.

4. Isla Bella Beach Resort (Marathon)

📍 Location: 1 Knights Key Blvd, Marathon, FL
🌐 Website: islabella.com

Why It’s a Must-Stay:
Located at the gateway to the Seven Mile Bridge, this sprawling, luxurious resort features five pools, a private sandy beach, and upscale dining. With waterfront rooms and a tranquil vibe, Isla Bella is perfect for those seeking a peaceful escape.

👉 Pro Tip: Rent a bike and explore the Seven Mile Bridge for incredible views.

5. Hawks Cay Resort (Duck Key)

📍 Location: 61 Hawks Cay Blvd, Duck Key, FL
🌐 Website: hawkscay.com

Why It’s a Must-Stay:
This family-friendly resort offers something for everyone—from a pirate ship pool for the kids to dolphin encounters and waterfront villas. Hawks Cay is also a great spot for fishing enthusiasts, with easy access to some of the best fishing waters in the Keys.

👉 Pro Tip: Book the sunset cruise for a magical evening on the water.

6. Tranquility Bay Beachfront Hotel & Resort (Marathon)

📍 Location: 2600 Overseas Hwy, Marathon, FL
🌐 Website: tranquilitybay.com

Why It’s a Must-Stay:
This laid-back beachfront resort combines spacious, villa-style accommodations with lush tropical landscaping. Relax at the adults-only pool or grab a mojito from TJ’s Tiki Bar and enjoy the breathtaking sunset views.

👉 Pro Tip: Try the lobster mac and cheese at the Butterfly Café—it’s unforgettable!

7. Little Palm Island Resort & Spa (Little Torch Key)

📍 Location: 28500 Overseas Hwy, Little Torch Key, FL
🌐 Website: littlepalmisland.com

Why It’s a Must-Stay:
Accessible only by boat or seaplane, Little Palm Island is pure luxury. With thatched-roof bungalows, oceanfront dining, and a no-cell-phones policy, this private island resort is perfect for a romantic getaway.

👉 Pro Tip: Indulge in the “Hook & Cook” experience, where you can catch your own fish and have it prepared by their chefs.

8. Casa Marina Key West, Curio Collection by Hilton (Key West)

📍 Location: 1500 Reynolds St, Key West, FL
🌐 Website: Casa Marina Key West

Why It’s a Must-Stay:
This historic resort, dating back to the 1920s, offers old-world charm with modern luxury. Located on a private beach, Casa Marina boasts elegant rooms, two oceanfront pools, and a prime location near Key West’s attractions.

👉 Pro Tip: Enjoy a cocktail at the Sun Sun Bar while watching the sunset from their private pier.

9. Oceans Edge Resort & Marina (Key West)

📍 Location: 5950 Peninsular Ave, Key West, FL
🌐 Website: oceansedgekeywest.com

Why It’s a Must-Stay:
Set on Stock Island, this luxurious resort offers spacious suites with private balconies, six pools, and a full-service marina. It’s a quieter alternative to the bustle of downtown Key West, but still close enough to enjoy the action.

👉 Pro Tip: Rent a kayak or paddleboard to explore the mangroves right from the marina.

10. The Marker Key West Harbor Resort (Key West)

📍 Location: 200 William St, Key West, FL
🌐 Website: themarkerkeywest.com

Why It’s a Must-Stay:
Located in the heart of Key West’s Historic Seaport, The Marker is a boutique resort with a vibrant, modern feel. Enjoy three pools, tropical gardens, and easy access to Key West’s famous attractions.

👉 Pro Tip: Stroll over to the nearby waterfront bars for live music and a quintessential Key West experience.

Which Resort Tops Your List?

Have you stayed at one of these incredible resorts, or do you have a hidden gem of your own? Reply to this email and let us know—we’d love to feature your recommendations in a future edition!

Wishing you tropical vibes and dreamy stays,
Brian

Florida Keys Road Trip Team

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