Top 15 Cool and Trendy Hotels in Islamorada 2023

Just 90 minutes south of Miami takes you to this mesmerizing village of islands, known as Islamorada. Here you will find a seamless blend of untouched bays, a quaint small-town atmosphere, locally owned restaurants, and a golden array of hotels all of which have sea views. From oceanfront boutiques to secluded, palm-tree-lined cottage residences, here are some of my favorite cool and trendy hotels in Islamorada, Florida…

Islander Resort l Global Grasshopper – travel inspiration for the road less travelled
Instagrammable Decor
Islander Resort
Cheeca Lodge Spa l Global Grasshopper – travel inspiration for the road less travelled
Boutique Style
Cheeca Lodge & Spa
Amara Cay Resort l Global Grasshopper – travel inspiration for the road less travelled
Beach Views
Amara Cay Resort
Best For Instagrammable Decor

Islander Resort

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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.


Tropical themed hotel

Tides Beachside Bar & Grill

Fun beach games

Outdoor pools


Pricey cabanas

No breakfast

Weak water pressure in shower

Best For Boutique Style

Cheeca Lodge & Spa

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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.


Luxurious accommodations

Open-air tiki bars

Adults-Only Lap Pool

Private beach


Thin walls

Bars and restaurants close early

No smart TVs

Best For Beach Views

Amara Cay Resort

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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.


Laid-back ambiance

In-pool loungers

Casual beer garden

On-site dining options


Not for budget-friendly crowd

Weak shower pressure

A bit noisy

Best For Millennials And Gen Zs

Hadley House Islamorada

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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.


A private marina

Budget-friendly rooms

Pet-friendly policies

Sweeping ocean views


Early check-in

No sitting area in rooms

Weak shower pressure

Best For Central Location

Fisher Inn Resort & Marina

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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.


Modern and bright accommodations

Boat parking and ramp

Sportfishing experience

BBQ facilities


Limited breakfast options

Pool is too warm

No elevator

Best For Families

Postcard Inn Beach Resort & Marina

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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. 


Nautical themed rooms

Iconic cocktails

Beachfront views

Private walk-in beach


Slow water pressure

Expensive drinks

Small bathroom space

Best For Beachside Location

Lime Tree Bay Resort

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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.


Caribbean-inspired style

A private fishing pier

Paddle boarding and kayaking

Florida’s key dishes


Crowded on weekends

Rooms are a little small

Few rooms are noisy

Best For Sea Views

Pelican Cove Resort & Marina

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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.


Sleek and stylish accommodations

8 different restaurant options

Walk-In Beach & Private Lagoon

Jet Ski Rentals & Tours


Pool is too warm

Lack of pool towels

Room can be small for big families

Best For Sports Bar

The Ocean View Inn & Sports Pub

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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.


Quirky vibrant rooms

Kicker Burgers

A cocktail pool

An outdoor spa


Low water pressure in the shower

Compact rooms

Late check-in

Best For Families

Angler’s Reef Resort

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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.


Nautical themed interior

Private boat dock

Landscaped gardens

A private beach area


Lack of towels

Bit crowded pool area

No on-site breakfast

Best For Budget-friendly

La Jolla Resort

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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.


Bright spacious accommodations

Near tourist attractions

Beachfront location

Free kayaking and paddleboarding


Limited parking

Rooms are not soundproof

Few rooms are a bit noisy

Best For Larger Groups

Casa Koto

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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.


Unique and trendy design

A fully furnished balcony

Private children’s playground

Cycling trips


Can get booked up

Larger groups only

Best For Couples

The Islands of Islamorada

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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.


Upscale unique accommodation

22 waterfront villas

On-site concierge service

An outdoor recreation space


No on-site restaurant

No on-site bar

Loud music

Best For Longer Stays

Pines & Palms Resort

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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.


Mid-century exterior

Private outdoor grills

Oceanfront swimming pool

Fully equipped kitchens


No on-site breakfast option

Small beach area

Weak water pressure in showers

Best For Outdoor Swimming Pool

Sunset Inn

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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.


Contemporary style

Outdoor Swimming Pool

Fully-equipped kitchenette

Keurig coffee maker


Small-sized pillows

Need more hooks in bathroom

Weak shower pressure

Best Hotels in Islamorada Ranked

The table compares the top 15 cool and trendy hotels in Islamorada.

Hotel NameLocationPrice Range (per night)Fitness FacilitiesDistance to Attractions (km)Nearby Restaurants
Islander Resort82100 Overseas Highway$459-$1159No0.42
Cheeca Lodge & Spa81801 Overseas Highway Mile Marker 82$224-$557Yes0.12
Amara Cay Resort80001 Overseas Highway$323-$746Yes2.73
Hadley House Islamorada82749 Overseas Highway$239-$489No1.43
Fisher Inn Resort & Marina84951 Overseas Highway$248-$399No0.22
Postcard Inn Beach Resort & Marina84001 Overseas Highway$199-$639No1.32
Lime Tree Bay Resort68500 Overseas Highway$139-$291No0.953
Pelican Cove Resort & Marina84500 Overseas Highway$213No0.61
The Ocean View Inn & Sports Pub84500 Overseas Hwy$237-$239No0.22
Angler's Reef Resort84977 Overseas Highway$2390No8.63
La Jolla Resort82216 Overseas Highwa$129-$279No0.83
Casa KotoIslamorada, 33036
The Islands of Islamorada82779 Old Highway$1850-$5600Yes1.63
Pines & Palms Resort80401 Old Highway$537-$1957No2.13
Sunset Inn82200 Overseas Highway$119-$129No1.753


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