Top 15 Cool and Trendy Hotels in Islamorada 2023

One of my favorite places, I love this incomparably grand getaway providing a serene slice of paradise. While visiting Islamorada’s most Instagrammable shoreline, I was surrounded by gently swaying palms along the deep turquoise of the Atlantic.

The tropical vibe extended into my 114 inviting rooms, the world-class restaurants, and the art-filled downtown area, creating a trip that will last a lifetime. While staying at this plush retreat, I experienced large, well-appointed rooms with ample outdoor space.

The resort’s ‘Tides Beachside Bar & Grill’ became my go-to spot, offering local flavors in a casual setting. I tried freshly caught seafood, signature sandwiches, and daily specials—all adding to the charm of my unforgettable stay.

Indulge in the allure of a unique tropical haven, where turquoise waters, towering palms, and gentle breezes create one of my favorite places. Cheeca Lodge in Islamorada became my sanctuary, a blend of romance, tranquility, and energy that few achieve.

While visiting this luxury escape, I reveled in the casual opulence and embraced a laid-back lifestyle. The 214 guestrooms and suites at Cheeca Lodge became my haven, each one a testament to excellence. Pillow-top mattresses, luxurious bath amenities, and plush bathrobes comforted me.

My stay was a journey through decades of design, where elegance seamlessly blended with a relaxed atmosphere. The three world-class restaurants and two open-air Tiki bars became my go-to spots, offering not just exquisite dining but also breathtaking views of the Atlantic.

Amara Cay is one of my favorite places for those who savor life’s small joys. While visiting, I love the constant hum of laughter and conversation, creating a casual beer garden vibe. The property exudes a hip charm, inviting me to simply soak up the tropical atmosphere.

While staying at Amara Cay, I found the guestrooms adorned in the fresh, natural hues of Islamorada, reflecting the easy-going elegance of the Florida Keys. My room featured either a king or two queen beds with premium bedding and trendsetting amenities, ensuring a comforting stay.

I tried the resort’s restaurant and bar, where I experienced exquisite cuisine rooted in the traditions of the Keys. Whether craving a custom-blended treat or a gourmet burger, I love that Amara Cay delivers a memorable dining experience.

This place is truly one of my favorite spots. Nestled in Islamorada, it offers easy access to all the must-try experiences in the area.

While staying at this top-notch oceanfront resort, I fell in love with the breathtaking views of pristine, white sandy beaches. The abundance of water adventures added a perfect touch to my experience.

What sets this hotel apart is its private marina equipped with a boat ramp and trailer parking. I tried out their budget-friendly rooms, and they exuded an intimate and exclusive vibe. Families can opt for the spacious suites, ensuring everyone stays together.

In every room, I appreciated the 50-inch TVs, the convenience of Keurig coffee makers, and the sweeping ocean views that truly made my stay unforgettable.

During my Islamorada visit, I discovered a modern, stylish, and comfortable getaway that quickly became one of my favorite places. The brand-new seaside accommodations, with their island décor and kitchenettes, provided an authentic Florida Keys experience. The naturally bright rooms added to the vibrant ambiance that I love.

While staying at the resort, I explored the grounds and found numerous picture-perfect spots for wedding photos. The tropical landscape of gorgeous Islamorada served as a stunning backdrop, making it a truly memorable experience.

Waking up to the gentle lull of waves on the sandy walk-in beach is a daily joy at one of my favorite places. Nestled on the sunrise side of Islamorada, it’s the ultimate launchpad for a day of thrilling water sports and unforgettable adventures.

The beachfront rooms, my chosen retreat, exude the essence of island living. From the crisp white linens to the distressed wood accents and vibrant navy, turquoise, and sky-blue nautical décor, the island style is unmistakable. But it’s the breezy balconies that stole my heart, offering mesmerizing views of the Marina and the Atlantic.

This haven, steeped in history since 1951, has been my go-to spot for iconic cocktails and a timeless beach atmosphere. 

Lime Tree Bay Resort is one of my favorite places—an authentic island oasis. Imagine a quarter mile of pristine white-sand beach adorned with charming tiki huts and inviting hammocks. During my stay, I cherished the moments at the private fishing pier, numerous swimming pools, and barbeque grills.

My highlight was having front-row seats to breathtaking Gulf sunsets—truly unparalleled in South Florida. The accommodations, freshly renovated, offered a range from studios and guestrooms to townhomes, each equipped with a host of amenities. The rooms featured comfortable furnishings and Caribbean-inspired décor, embodying the laid-back lifestyle of the Florida Keys.

What sets this experience apart is the unlimited access to paddle boards, kayaks, bicycles, and tennis racquets. While visiting, I tried them all, creating lasting memories with my loved ones.

Staying at Pelican Cove Resort & Marina was like stepping into a tropical haven right from when I arrived. This place perfectly captures the laid-back vibe of the Florida Keys. Tucked into a seaside garden, it offers 63 chic guestrooms adorned with crisp cotton bedding, wooden furnishings, bursts of tropical hues, and captivating original artwork.

My room featured a wall-mounted flat-screen TV with premium cable for entertainment, and the private balcony treated me to breathtaking horizon views. Opting for an oceanfront room was a game-changer. I witnessed pelicans diving for their daily catch, spot a playful dolphin pod, and let the soothing sound of waves kissing the shore lull me into serenity.

The resort’s dining experience was equally enchanting. I indulged in local specialties, making my stay here one of my favorite experiences.

Nestled in this tropical paradise, one of my favorite places offers a local paradise and a traveler’s delight. From my own patio, I soaked in the low oasis setting, complete with an outdoor spa leading to a charming cocktail pool.

During my stay, I enjoyed leisurely strolls down the property’s dock, treated to a breathtaking bay view with small boat access. A must-visit was the pub, where I indulged in the famous Kicker Burgers and exquisite sea-to-table fare.

Every room, surrounded by lush tropical landscapes, had its private path to the inviting pool. The inspired design, reminiscent of the tropical flair of the Florida Keys, prioritized cleanliness and comfort.

In 2003, the resort underwent a captivating transformation, culminating in the addition of a stunning new swimming pool. The sports bar, a renovated gem, served as a popular watering hole for both tourists and locals alike, adding to the vibrant charm of my unforgettable experience.

Nestled in this charming Caribbean fishing village-style retreat, it quickly became one of my favorite places for an unforgettable vacation in Islamorada.

With 52 cottages echoing Native Conch and British West Indies influences, I love how the landscaped gardens exude a unique charm that captivates from when you arrive.

During my stay, having access to the resort’s private boat dock was a game-changer. Exploring the waters became a breeze, from snorkeling adventures to anchoring at a sand bar for a leisurely lunch.

Surrounded by over 500 feet of oceanfront and mangroves, the resort is perfectly situated for aquatic excursions. I couldn’t believe my luck—just three miles offshore lies the only living coral barrier reef at the famed Alligator Reef.

Retreat back to a simpler time at this bayside haven, one of my favorite places teeming with the classic Keys style. I love how it reconnects you with the carefree spirit and opulent comforts of ‘Old Florida’, thanks to its careful design and fresh, natural hues.

While visiting, I stayed in one of the resort’s six retro-style buildings, and I was impressed by how they’ve been updated. My room had a kitchenette and an outdoor seating area, adding a personal touch to the experience. The modern amenities and bespoke décor contributed to a lavish charm, making me feel truly comfortable in this ‘home from home’.

One of the highlights was the resort’s ideal location. Being right on the beautiful beachfront and within walking distance of Islamorada’s top attractions, I experienced the convenience it offered to families and visitors alike.

Casa Koto quickly became one of my favorite places. Modern elegance blended seamlessly with old-world charm in this stunning six-bedroom hacienda, spanning three levels and set against the breathtaking backdrop of White Marlin Beach.

While visiting, the private beach became my go-to spot, but when indoors, I couldn’t resist the allure of the second-level furnished balcony. It was the perfect place to unwind with a refreshing beverage or showcase my culinary skills on the gas grill.

Stepping inside, the cool tile floors and charming personal touches created a welcoming atmosphere. What stole my heart even more was the on-site children’s playground and the opportunity for beautifully landscaped cycling trips right from the property.

I love this stunning resort that seamlessly weaves familiar, lavish comforts with the allure of tropical beauty. While visiting, I meandered down coconut palm-shaded walkways into the Gulf Stream, creating unforgettable memories with my family. The enclave comprises 22 waterfront villas, each featuring four bedrooms, full kitchens, and outdoor recreation spaces.

For smaller parties like mine, there are eight one-bedroom suites, each with its own beachside setting. I stayed at one of these, enjoying the personalized and intimate experience centered around the lure of island life. The on-site concierge service connected me to the very best of the Florida Keys, making it one of my favorite places for a getaway.

One of my favorite places, this enchanting retreat maintains its original 1930s charm. Twenty-four classic cottage-style bungalows, connected by white sand paths, embraced me between whispering trees.

While staying at this magical haven, I could taste the wind and listen to the stars. Time stood still, and my dreams came to life in this serene escape.

I love this—each cottage boasts full kitchens and a private outdoor grill. I savored my feasts in the comfort of my secluded haven, gazing at dreamlike ocean views.

The accommodations seamlessly blend mid-century exterior charm with modern interior décor. I experienced a perfect combination of functionality, style, and class.

One of my favorite places to recharge is this unique resort that seamlessly blends modern design with a touch of Floridian charm, creating a nostalgic yet contemporary retreat.

While staying at this haven, I loved the spacious guestrooms adorned with modern island décor. The mini fridge and a 50-inch HDTV added a convenient touch. The plush-top mattresses and carefully chosen luxury linens ensured a night of pure bliss. What I found delightful was that some rooms even featured a kitchenette, complete with a full-size countertop, an upgraded dual fridge, a microwave, and a Keurig coffee maker.

Located just an hour and a half’s drive from the vibrant energy of Miami, I experienced the joy of knowing that incredible adventures were just a day trip away.