Just 90 minutes south of Miami takes you to this mesmerising village of islands, known as Islamorada. Offering a bountiful array of activities from water sports to eco-tours, and a focus on the conservation of critical habitat, here you will enjoy a seamless blend of untouched bay and ocean views, a quaint small-town atmosphere, and locally owned restaurants.
Islamorada boasts numerous tranquil spots to relax under the glorious rays of the tropical sunshine, an essence which radiates into its golden array of hotels. From oceanfront boutiques to secluded, palm-tree-lined cottage residences, here are the best cool and unusual hotels in Islamorada, Florida (in no particular order)…
1. Islander Resort – a quirky, trendy and Instagrammable accommodation located on Islamorada’s most picturesque shoreline
Here we have an incomparably grand getaway which offers you a serene slice of paradise. Situated on Islamorada’s most Instagrammable stretch of shoreline, your stay will be surrounded by gently swaying palms bordering the deep turquoise of the Atlantic.
The tropical vibe which spreads into the 114 inviting rooms, the world-class restaurants, and the art-filled downtown area compound to form a trip that will last for a lifetime.
The plush rooms feature large floor plans with ample outdoor space, and thoughtfully appointed furnishings. The resort’s ‘Tides Beachside Bar & Grill’ serves local flavours in a casual setting, ranging from freshly caught seafood, signature sandwiches, and daily specials.
2. Cheeca Lodge & Spa – an elegant, lavish boutique accommodation located on 27 acres of private turquoise waters and white sand oceanfront
Whisk yourself away to a unique tropical splendour, and indulge your mind, body, and spirit in an oasis of turquoise waters, towering palms, and calm breezes.
A sense of romanticism, serenity, and dynamism combine to form a standard of excellence achieved by few, where you can be swept away by casual opulence in a laid-back lifestyle. Setting the standard for luxury Islamorada hotels, Cheeca Lodge offers 214 spacious guestrooms and suites which offer lavish comforts such as pillow-top mattresses, luxury bath amenities, and plush bathrobes.
These rooms exude elegance in a relaxed atmosphere, honed over decades of design work, while the three world-class restaurants and two open-air Tiki bars further boast sweeping Atlantic views.
3. Amara Cay Resort – a hip, elegant and stylish accommodation overlooking the beach with a laid-back atmosphere
For those of you who appreciate life’s little moments, Amara Cay is a constant hum of laughter and conversation.
With a casual beer garden, a hip charm permeating the property, and an inviting allure, this is a spot to simply soak up the tropical atmosphere. Each of the guestrooms are decorated in the fresh, natural hues of Islamorada, and infused with the easy-going elegance of the Florida Keys.
All come with a king or two queen beds, premium bedding, and trendsetting amenities to ensure a comforting stay. The resort’s restaurant and bar offer exquisite cuisine anchored in the traditions of the Keys.
Whether you are after a custom-blended treat or a delicious gourmet burger, a memorable dining experience is offered.
4. Hadley House Islamorada – a beautiful, chic and pet-friendly accommodation where guests can enjoy nearby popular attractions, perfect for Millennials and Gen Zs
This beautifully designed establishment is idyllically situated with nearby access to all of Islamorada’s most popular excursions. As a top-of-the-range oceanfront resort, a stay here will be characterized by extensive views of pristine, white sandy beaches, and bountiful opportunities to indulge in water adventurers.
The hotel boasts its very own marina, with a private boat ramp and trailer parking. Guestrooms range from budget-friendly rooms which evoke a sense of intimacy and exclusivity, to large suites where families can stay together.
Some common factors between all the rooms are the 50-inch TVs, the Keurig coffee makers, and the sweeping ocean views which will make for an unforgettable stay.
5. Fisher Inn Resort & Marina – a modern, stylish and bright accommodation located in the heart of Islamorada
Dive into a modern, stylish, and comfortable getaway during your Islamorada visit. Evoking an authentic Florida Keys experience, the brand-new, naturally bright seaside accommodations feature island décor and kitchenettes, topped with a vibrant ambiance.
The resort grounds further boast plenty of picture-perfect areas for wedding photos, backdropped by the tropical landscape of the gorgeous Islamorada.
6. Postcard Inn Beach Resort & Marina – an ocean-chic, contemporary and family-friendly accommodation is a favorite for a beach and boating getaway
From the sandy shores of the walk-in beach, picture-perfect postcard moments await you at this breathtaking resort.
Located on the sunrise side of Islamorada, it is near-impossible to find a better spot to wake up, before embarking on a day filled with water sports and life-lasting adventures.
Each of the beachfront rooms ooze a typical island style, from crisp white linens and distressed wood accents, to pops of navy, turquoise, and sky-blue nautical décor.
Breezy balconies with Marina and Atlantic views are the icing on the cake. Serving up iconic cocktails and nostalgic beach vibes since 1951, this sprawling resort is full of life and charm.
7. Lime Tree Bay Resort – a newly renovated, vibrant beachside accommodation offering a modern and Caribbean-inspired style stay
The epitome of a true island oasis, Lime Tree Bay Resort boasts a quarter mile of white-sand beach dotted with tiki huts, hammocks, a private fishing pier, multiple swimming pools, and barbeque grills.
Topped off with front-row seats to the most awe-inspiring Gulf sunsets, this resort is unmatched anywhere else in South Florida. The freshly renovated accommodations range from studios and guestrooms to town homes and feature a comprehensive list of amenities.
All have been upgraded with comfortable furnishings and Caribbean-inspired décor to create a casual lifestyle synonymous with the Florida Keys.
Guests can also enjoy unlimited use of paddle boards, kayaks, bicycles, and tennis racquets, to create lasting memories with loved ones.
8. Pelican Cove Resort & Marina – a classic, charming and relaxed accommodation ideal for those looking to embrace the local culture
A stay here will transport you to a tropical paradise from the minute you arrive. Embodying the relaxed lifestyle of the Florida Keys, Pelican Cove Resort & Marina is nestled into a seaside garden and boasts 63 sleek and stylish guestrooms with crisp cotton bedding, wood furnishings, pops of tropical colour, and original artwork.
Further in-room offerings include a wall-mounted flat-screen TV with premium cable access, and a private balcony with impeccable horizon panoramas.
The oceanfront rooms allow you to watch pelicans dive for fresh fish, catch a sight of a dolphin pod, and listen to the waves lap at the shore. A tranquil dining experience is offered at the resort, where you can sample local specialties.
You can stroll down the property’s dock towards a breathtaking bay view which includes small boat access, or stop into the pub to taste the famous Kicker Burgers and exquisite sea-to-table fare.
Each room is girdled by lush tropical landscapes and its very own path to the pool. Inspired by the tropical flair of the Florida Keys, the emphasis is on cleanliness and comfort.
2003 saw the final phase of the resort’s makeover, with the addition of a gorgeous new swimming pool, and a renovated sports bar which is a watering hole for both tourists and locals alike.
Dotted by 52 cottages inspired by Native Conch and British West Indies, the meticulously landscaped gardens boast a rather unique charm.
The resort’s private boat dock makes getting around on water so much more attainable, meaning you can head out on snorkelling trips before dropping anchor for lunch at the sand bar.
Perfectly poised for aquatic excursions, the resort is framed by more than 500 feet of oceanfront and mangroves, while the only living coral barrier reef is located only three miles offshore in the famed Alligator Reef.
11. La Jolla Resort – a retro, bright and contemporary accommodation providing complimentary kayaks and paddleboards
Retreat back to a simpler time, in this bayside haven teeming with the classic Keys style. You will be reconnected with the carefree spirit and opulent comforts of ‘Old Florida’, owing to the careful design and fresh, natural hues.
Each of the resort’s six retro-style buildings have been updated, and the guestrooms boast kitchenettes, as well as outdoor seating areas. Modern amenities and bespoke décor contribute to a lavish charm, guiding guests to feel comfortable in this ‘home from home’.
Families and visitors can all benefit from the resort’s ideal location, which boasts a beautiful beachfront location, and is within walking distance to Islamorada’s top attractions.
12. Casa Koto – a unique, trendy and upscale accommodation steps away from the beach
At Casa Koto, modern elegance meets old-world antique charm in a casual, refined setting. This stunning three-level, six-bedroom hacienda is the perfect destination for your next reunion, backdropped by breathtaking vistas of White Marlin Beach.
When you’re not out enjoying the private beach, the property’s second-level furnished balcony is the ultimate spot to savour a refreshing beverage or cook up a feast on the gas grill.
The interior features a welcoming living space dressed in cool tile floors, and many attractive personal touches. The site boasts its very own children’s playground, and beautifully landscaped cycling trips can be enjoyed from the minute you venture out of the property.
To book, check prices or availability for Casa Koto
13. The Islands of Islamorada – an upscale, unique and beautiful accommodation surrounded by tropical paradise is ideal for a relaxing getaway
Seamlessly weaving familiar, lavish comforts with the allure of tropical beauty, a captivating experience is created at this stunning resort.
From the coconut palm-shaded walkways, you can meander down into the Gulf Stream, and share an unforgettable memory with your family. 22 waterfront villas make up this well-appointed enclave, each offering four bedrooms with full kitchens and an outdoor recreation space.
Eight one-bedroom suites are available for smaller parties, each boasting its very own beachside setting. Centred around the lure of island life, this resort offers a uniquely charming, personalized, and intimate experience, through an on-site concierge service which can connect you to the very best of the Florida Keys.
14. Pines & Palms Resort – a cool, charming and classic accommodation well equipped for a fun and memorable vacation
Maintaining its original 1930’s charm with 24 classic cottage-style bungalows connected by white sand paths, a stay here will tuck you away between whispering trees.
A magical place where you can taste the wind and listen to the stars, here you will find that time stands still, and dreams come to life. Each cottage features full kitchens, as well as your very own private outdoor grill, meaning you can savour your feasts within the comfort of your own secluded haven, overlooking dreamlike ocean views.
These accommodations beautifully blend a mid-century exterior style with simplistic, modern interior décor, whilst offering functionality, style, and class.
15. Sunset Inn – a petite, cozy and iconic accommodation within walking distance to the best shopping and local cafes
The perfect spot to recharge your mind, body, and soul, this one-of-a-kind resort boasts a contemporary design with a dash of Floridian flair, and a nostalgic throwback to a simpler time.
The spacious guestrooms feature modern island décor, a mini fridge, and a 50-inch HDTV. The plush-top mattresses and carefully selected luxury linens make for a blissful night’s sleep, and some rooms boast their very own kitchenette which comes with a full-size countertop, an upgraded dual fridge, a microwave, and a Keurig coffee maker.
Situated an hour and a half’s drive from the hustle and bustle of Miami, unimaginable experiences are just a day trip away.
To book, check prices or availability for Sunset Inn
My first true adventure began as a six month voyage around South East Asia as a fresh faced backpacker and ever since I’ve lived a semi nomadic existence, clocking up visits to over 40 countries. I’m a lover of US Road Trips, deserted beaches bathed in warm glow of a sunset, Cuban mojitos, travel destinations far away from the tourist crowds and all things Scandinavian – from cloudberry liquors to Nordic noirs. When not wandering the world and running Global Grasshopper, you’ll find me walking my rescued Greek street dog in leafy South West London, strolling around the Brighton Lanes on random day trips, hunting for photogenic landscapes or daydreaming about my favourite places; Havana, Copenhagen, Italy, Laos, California and the surreally beautiful landscapes of a wintry Iceland.
