Best Hotels in Islamorada, FL

Explore the Best Hotels in Islamorada, FL

This guide to the best luxury, 5-star, and design-forward hotels in Islamorada, USA is manually curated by our editorial team based on first-hand research, verified guest reviews, location analysis, and overall service quality. Each hotel is selected to meet high standards of comfort, authenticity, and guest experience.

Cheeca Lodge & Spa
Hotels
Islamorada, FL, USA

Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot fishing pier. Each guestroom includes dark hardwood furniture and a balcony with views of the resort. Guests can watch movies on the 42-inch flat-screen TV with DVD player or browse the internet with free WiFi. An in-room safe and coffee maker are also provided. Adult and family-style swimming pools can be enjoyed at the resort. Additionally, a fully equipped fitness center, 6 tennis courts, and a full-service watersports facility are open to guests. Three restaurants and a tiki bar are located on-site at Cheeca Lodge & Spa. Atlantic’s Edge offers tropically-inspired cuisine amid a classic décor while Nikai Sushi Bar & Restaurant serves nigiri, sashimi, and more. Downtown Key Largo is a 20-minute drive from Cheeca Lodge & Spa. Long Key State Park is 13.7 miles from the resort.

Guest Reviews:

- "It was a wonderful experience." - "I was visiting for my birthday and it was one of the most beautiful places I’ve ever visited. The people were very welco" - "Took my 20-year-old niece with me I don’t think it’s a great place for younger kids" - "Did enjoy" - "Great romantic place to stay with gorgeous views from everywhere." - "Great facility warm and informative employees" - "Spectacular but make sure you’re not next door to any noisy dogs!"

Islander Resort
Hotels
Islamorada, FL, USA

A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. Relax and enjoy beautiful views from fully furnished private porches or lanais. Spend the afternoon lounging by the Islander's 2 on-site swimming pools. Enjoy on-site dining at Beachside Bar and Grill. Easily discover a variety of activities only minutes from the Islander Resort, including snorkeling and scuba diving. Enjoy deep-sea fishing, sailing or browsing the local shops, also only a short distance away.

Guest Reviews:

- "We enjoyed our stay room was beautiful clean and wonderful staff. We enjoyed all the amenities that were offered! We" - "Private, secluded, uncrowded, and dog-friendly!" - "Stay longer" - "The location was perfect and close to restaurants in the area. Hope to return !" - "Will definitely return!" - "A relaxing stay with polite and attentive staff. The location is perfect for restaurants and attractions within walking" - "Relaxing time at a beautiful smallish resort on the beach!"

Amara Cay Resort
Hotels
Islamorada, FL, USA

This beachfront hotel is located in Islamorada, Florida and features transfer services within 3.7 mi from the property. WiFi is included in the resort fee. Guests can relax on beachside hammocks or enjoy the outdoor pool at Amara Cay Resort. An on-site fitness center is available, as well as a meeting space. A flat-screen TV, work desk, and safety deposit box comes standard in every guestroom. Bicycle rentals and luggage storage are offered on site. Sample a custom cocktail at the Tiki Bar or experience Amara Cay Resort’s restaurant, ReelCatch. The History of Diving Museum is 3 mi away. Guests will be 8 minutes’ drive from Anne’s beach. Windley Key Fossil Reef Geological State park is 8 minutes’ drive.

Guest Reviews:

- "Good price, beautiful grounds" - "Stunning stunning" - "Excellent" - "We had such a beautiful family vacation at Amara Cay we will definitely be returning." - "The best place for relax and romantic" - "Lovely staycation in Islamorada!" - "Had a great stay. Thank you" - "Amazing" - "Beautiful place and location. Great pool and pool bar!" - "Relaxing and exactly what we needed" - "The resort was great. Room service disappointed as they wouldn't report left items."

La Siesta Resort & Villas
Hotels
Islamorada, FL, USA

Just off the Overseas Highway and in front of the ocean, this Islamorada hotel offers an on-site marina. The beachfront hotel features an outdoor pool. WiFi is included in the resort fee. The suites and cottages at La Siesta Resort & Villas are equipped with a cable TV and air conditioning. On site, SIDECAR bar serves light fares, beer, and wine daily. Activities such as boating, fishing, jet skiing and snorkeling can be arranged. The on-site marina offers both gulf-side and ocean-side slips while non-motorized watersports equipment and bicycles are provided for guests' use. Theater of the Sea is 3.7 mi away from the accommodations while Anne's Beach is located 6.7 mi away.

Guest Reviews:

- "A piece of paradise." - "Would not have wanted to stay anywhere but at La Siesta!" - "Wish we could have stayed, hope to go again." - "Absolutely Perfect" - "Tropical vacation in the US, we loved it!" - "A great location with exceptional rooms that exceeded my expectations" - "We had a wonderful stay in a beautiful comfortable clean cabana." - "I’m very happy with the Resort" - "Great location with amazing ocean views."

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hotels
Islamorada, FL, USA

Featuring a unique tropical atmosphere and located on an island in the Florida Keys, this resort offers WiFi and parking to guests. A cable TV and a private bathroom are included in every guestroom. A in-room safes is also provided. Guests of Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort can stop by the marina to charter a fishing trip or rent a jet ski. Guests seeking adventure will enjoy snorkeling and diving charter boats. Windley Key Fossil Reef Geological Park is just 3 minutes’ drive from the property while Key Largo is 21 minutes’ drive.

Guest Reviews:

- "Was impressed 10 stars" - "Amazing.highly recommend" - "Magnificent views - great staff - will be back!" - "Last minute booking saved the weekend!" - "WONDERFUL RESORT / STAY / SERVICE!!!" - "Beautiful birthday stay with my husband." - "Amazing" - "Had a wonderful time" - "We had a nice 5 days there" - "We will return!" - "Nice clean resort friendly staff, good location." - "A little bit or paradise"

Fisher Inn Resort & Marina
Hotels
Islamorada, FL, USA

Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games on the property. Free Wi-Fi is included in all rooms of this Islamorada hotel and guests can also enjoy cable TV in the rooms. Some units offer a kitchenette so guests can prepare their own meals during their stay. Laundry facilities is available on site at the Fisher Inn Resort & Marina. Guests will also be able to enjoy various activities such as fishing, windsurfing, kayaking, paddle boarding and snorkeling during their stay. This oceanfront hotel is less than 10 minutes’ walk from the Theater of the Sea. The Holiday Isle Marina is also less than 1 mile away.

Guest Reviews:

- "Great quite Hotel" - "This was a great place for my weekend stay." - "Loved it here" - "Had a great time. Grand daughter enjoyed the pool and all of the games" - "Will go back for sure!!" - "Comfortable, clean and convenient location with great ocean view." - "Good but the pet fee should be $25 per day instead of $50 considering housekeeping only made the beds, supplied fresh to" - "We love the fisher inn and will continue to stay there!"

Topsider Resort
Hotels
Lower Matecumbe Beach, FL, USA

Topsider Resort features free bikes, outdoor swimming pool, a garden and private beach area in Lower Matecumbe Beach. Featuring family rooms, this property also provides guests with a grill. Guests can use the hot tub, or enjoy pool views. The hotel will provide guests with air-conditioned rooms offering a closet, a coffee machine, a fridge, a dishwasher, a safety deposit box, a flat-screen TV, a terrace and a private bathroom with a shower. Free WiFi is available to all guests, while some rooms come with a balcony. All guest rooms will provide guests with an oven. Activities such as fishing, snorkeling, canoeing can be enjoyed in the surrounding areas, and guests can relax along the beachfront. Sea Oats Beach is a 7-minute walk from Topsider Resort, while Upper Matecumbe Key is 6.5 miles away. Key West International Airport is 73 miles from the property.

Guest Reviews:

- "A perfect location" - "Lovely !" - "Love peaceful beach location with everything you need!" - "wonderful relaxing time" - "Nice place but rooms need to be rehabbed."

Casa Morada
Hotels
Islamorada, FL, USA

Located in Islamorada, a 10-minute walk from Upper Matecumbe Key, Casa Morada has accommodations with free bikes, free private parking, an outdoor swimming pool and a garden. With a terrace, the 5-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The hotel provides a hot tub and luggage storage space. At the hotel, every room has a closet. Rooms come with a coffee machine, while some rooms include a balcony and others also feature sea views. The rooms in Casa Morada are equipped with a flat-screen TV and free toiletries. Guests at the accommodation can enjoy a buffet breakfast. Theater of the Sea on Islamorada is 2.3 miles from Casa Morada, while Windley Key is 2.9 miles from the property. Miami International Airport is 75 miles away.

Guest Reviews:

- "Best hidden gem in the keys" - "Overall great stay. Comfortable beds and room. And right next to where we wanted to be." - "Amazing place" - "A wonder escape from Miami" - "CLASSIC ESTABLISHMENT A MUST VISIT" - "perfect in every way" - "We found a hidden gem at Casa Morada. We plan to go again next year." - "Excellent!" - "It was a very nice stay. The reception was very helpful. Great outdoor area." - "Beautiful and relaxing environment"

Pines & Palms Resort
Hotels

This Islamorada resort in the Florida Keys is located near Alligator Reef. It features an oceanfront freshwater pool, a Tiki Bar and a private beach area. Each accommodations includes a full kitchen. A living area with a cable TV is included in all units at Pines & Palms Resort. The traditionally styled units feature light colors and island decor. Most offer a private terrace with ocean views. Guests at Resort Palms & Pines have access to kayak and bike rentals, private boat docks and premium sport fishing areas. A covered cabana with a barbecue grill, fridge and sink is available for guest use. This resort is less than 1 mi from Miss Islamorada Fishing Charters. The entrance to John Pennekamp Coral Reef State Park is less than 30 minutes’ drive away.

Guest Reviews:

- "Amazing stay!" - "Rest and relaxation" - "Amazing stay" - "Wish we could've stayed longer. We hope to get a chance to return." - "Home away from home" - "Palms & Pines - our home away from home - so glad we chose this place!" - "Family weekend" - "Strategic position!" - "Exceptional stay" - "Great place to stay in the keys." - "Relaxing getaway, you feel like your on a Caribbean island without leaving the states."

Chesapeake Beach Resort
Hotels
Islamorada, FL, USA

Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away. A 37-inch flat-screen cable TV and a small refrigerator are offered in each room at this Florida Chesapeake Beach Resort. Select rooms and suites have a balcony. Chesapeake Beach Resort features an outdoor pool with an ocean view. Guests can check out the History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive).

Guest Reviews:

- "My husband and I took a vacation. The Chesapeake resort was so relaxing so beautiful so very clean in the hospitality wa" - "Love it" - "Bewutiful, tranquil, relaxing. Very clean and the staff was exceptional!" - "The staff was very helpful, pleasant and friendly."

Islamorada, USA Hotels with Parking

best hotels in Islamorada, USA
8.7
1451 reviews
From $348

Islander Resort offers seamless parking solutions that enhance your travel experience in Islamorada. Guests can enjoy secure and convenient parking facilities, ensuring a hassle-free arrival and departure. With efficient transit options, you'll have more time to explore the nearby attractions without worrying about your vehicle. Enjoy peace of mind knowing that your car is safe while you immerse yourself in all the exciting activities the Florida Keys have to offer.

best hotels in Islamorada, USA
8.1
607 reviews
From $254

Experience seamless arrival with hassle-free parking at this beachfront resort, designed to enhance your travel experience. Enjoy secure parking facilities that ensure peace of mind while you explore the beautiful surroundings of Islamorada. With convenient access to the hotel’s amenities and nearby attractions, you’ll spend less time worrying about logistics and more time indulging in the vibrant local culture and stunning ocean views.

best hotels in Islamorada, USA
8.7
977 reviews
From $865

Enjoy hassle-free transit with efficient parking solutions available at this luxury resort in Islamorada. Guests can take advantage of secure and convenient parking options, ensuring a seamless arrival and departure experience. Spend less time worrying about logistics and more time enjoying the resort's stunning amenities and lush surroundings. With safety as a priority, you can focus on making lasting memories without the stress of parking hurdles.

best hotels in Islamorada, USA
8.3
339 reviews
From $240

Enjoy hassle-free transit at La Siesta Resort & Villas with convenient parking options that ensure a seamless arrival. Rest easy knowing your vehicle is secure while you explore the beautiful surroundings of Islamorada. Whether you're heading out for a day of adventure or returning after a fun night, our efficient parking facilities make your travel experience smooth and stress-free, allowing you to focus on creating lasting memories.

best hotels in Islamorada, USA
8.4
26 reviews
From $649

Enjoy a hassle-free arrival at this resort with secure parking conveniently available for all guests. Your journey begins smoothly as you glide into an efficient parking experience, allowing you to focus on relaxation and adventure. With ample space and safety measures in place, you can explore the beautiful surroundings without worry. This thoughtful aspect of your stay ensures seamless transit, making it an excellent choice for travelers who value easy logistics during their getaway.

Islamorada, USA Family Friendly Hotels

best hotels in Islamorada, USA
8.1
607 reviews
From $254

Amara Cay Resort is a haven for families seeking stress-free bonding time. With spacious accommodations designed for comfort, parents can relax knowing their children are safe and entertained. Join in on engaging activities tailored for kids, ensuring everyone enjoys their vacation. The resort’s easy access to the beach offers plenty of opportunities for family fun, creating lasting memories together amidst the sun and surf.

best hotels in Islamorada, USA
8.7
1451 reviews
From $348

At Islander Resort, families can enjoy a stress-free escape with spacious accommodations designed for bonding and relaxation. Kids will find hours of enjoyment with nearby activities like snorkeling, while parents appreciate the safe and welcoming environment. With convenient access to local attractions, there's something for everyone, making it the perfect spot for family adventures. Create lasting memories together as you explore the beautiful surroundings of the Florida Keys.

best hotels in Islamorada, USA
8.7
977 reviews
From $865

This family-friendly resort in Islamorada offers a safe and welcoming environment for guests of all ages. With spacious accommodations and a variety of engaging activities, families can bond over swimming in the adult and kid-friendly pools or exploring the beautiful grounds. On-site restaurants cater to diverse tastes, making mealtime stress-free. Enjoy peace of mind while your children explore the resort's many amenities, providing a perfect backdrop for cherished family moments.

best hotels in Islamorada, USA
8.3
339 reviews
From $240

Families will find a welcoming environment at La Siesta Resort & Villas, designed to ensure safety and stress-free bonding moments. With spacious accommodations and easy access to family-friendly activities like fishing and snorkeling, you can enjoy quality time together without worry. The nearby beach provides a perfect playground for children, while parents appreciate the relaxed atmosphere that allows them to connect with loved ones in a wholesome, secure setting.

best hotels in Islamorada, USA
8.4
26 reviews
From $649

Families will find a welcoming oasis at this resort, where children can engage in exciting activities while parents unwind. Safety is prioritized, allowing you to relax knowing your loved ones are secure. With spacious accommodations and opportunities for stress-free bonding, this family-friendly destination in the Florida Keys invites you to make lasting memories together. Embrace quality time in a nurturing environment designed for all ages, ensuring every family member feels right at home.

Islamorada, USA Hotels with Private Beach

best hotels in Islamorada, USA
8.3
339 reviews
From $240

Escape to tranquility at La Siesta Resort & Villas, where direct access to a pristine private beach awaits. Lounge on soft sands under swaying palms, far from the hustle and bustle of crowded tourist spots. The serene beachfront setting is perfect for unwinding while taking in the breathtaking ocean views. Immerse yourself in nature's beauty as you enjoy exclusive access to your own slice of paradise, making every moment truly special.

best hotels in Islamorada, USA
8.4
26 reviews
From $649

Escape to a serene paradise with direct access to soft sandy shores, where you can unwind in absolute tranquility. This elite resort offers guests a private beach experience, perfect for sunbathing or leisurely strolls along the coast. Feel the gentle waves lapping at your feet as you savor your escape from the crowds. Revel in the breathtaking views and the calming ambiance of this exclusive beachfront retreat in Islamorada, where luxury meets natural beauty.

best hotels in Islamorada, USA
8.7
1451 reviews
From $348

Escape to your own serene paradise with direct access to soft sandy shores at Islander Resort. This elite beachfront retreat in the Florida Keys allows you to unwind in tranquil surroundings, far from crowded tourist areas. Immerse yourself in the soothing sounds of the ocean while lounging on a private porch or lanai, and enjoy the breathtaking views of the coastline. Retreat from the hustle and bustle, and indulge in a peaceful beach experience tailored for relaxation.

best hotels in Islamorada, USA
8.1
607 reviews
From $254

Escape to tranquility at this exclusive beachfront getaway, offering direct access to soft sandy shores. Experience serene moments as you lounge in beachside hammocks, soaking up the sun without the crowds. With stunning ocean views from your room, this elite destination provides a perfect backdrop for relaxation and rejuvenation. Whether taking long walks along the shore or enjoying quiet afternoons, blissful serenity awaits at this idyllic coastal retreat.

best hotels in Islamorada, USA
8.7
977 reviews
From $865

Escape the crowds and unwind on serene private waterfront at this luxury resort in Islamorada. Guests enjoy exclusive access to 1000 feet of pristine shoreline, where soft sands and tranquil waters create the ultimate beach getaway. Immerse yourself in nature as you relax on your balcony, taking in breathtaking views. Experience the luxurious ambiance that ensures a peaceful retreat, allowing you to savor the beauty of Florida's coastline in an elite atmosphere.

Islamorada, USA Pet Friendly Hotels

best hotels in Islamorada, USA
8.4
26 reviews
From $649

Bring your furry friends along for an unforgettable vacation at this pet-friendly resort, where no family member gets left behind. With dedicated pet amenities and nearby parks for enjoyable walks, you can bond with your pets while exploring the stunning surroundings of Islamorada. Enjoy peace of mind knowing that your beloved companions are welcome in this vibrant atmosphere, creating memorable moments together as you embark on new adventures with your whole family.

best hotels in Islamorada, USA
8.7
1451 reviews
From $348

Bring your furry family member along to Islander Resort, where pets are welcomed with open arms! With pet-friendly amenities and nearby walking areas, your four-legged friend can enjoy their vacation too. Experience the joy of having no family member left behind while you explore the beautiful beaches and vibrant local attractions. Create unforgettable memories together, making every moment of your getaway enjoyable for both you and your beloved pet.

best hotels in Islamorada, USA
8.3
339 reviews
From $240

At La Siesta Resort & Villas, no family member gets left behind! This pet-friendly retreat welcomes your furry friends with open arms, offering comfortable accommodations equipped with essential amenities for pets. Enjoy leisurely strolls along the beach or explore nearby walking trails, ensuring your pets have just as much fun during your getaway. Create cherished memories together in a warm and inviting environment that values the companionship of all family members.

best hotels in Islamorada, USA
7.7
1006 reviews
From $205

At Fisher Inn Resort & Marina, no family member gets left behind—your beloved pets are warmly welcomed! Enjoy pet-friendly amenities designed for comfort and convenience, allowing you to create lasting memories together. With nearby walks and open spaces, your furry friends will love the adventure just as much as you do. This inclusive atmosphere ensures that every family member, including your pets, feels right at home during your stay.

best hotels in Islamorada, USA
8.1
607 reviews
From $254

At this welcoming beachfront resort, no family member is left behind. Enjoy a pet-friendly atmosphere complete with amenities designed for your furry companions. Explore the nearby scenic trails and beaches, perfect for leisurely walks with your beloved pets. With relaxed accommodations and a focus on comfort, both you and your pets can enjoy a stress-free getaway in the heart of Islamorada’s natural beauty.

Islamorada, USA Hotels with Entertainment

best hotels in Islamorada, USA
8.7
977 reviews
From $865

Experience the vibrant nightlife and exhilarating activities at this luxury resort in Islamorada, Florida. With three on-site restaurants and a lively tiki bar, guests can indulge in delicious dining and refreshing cocktails without leaving the premises. The extensive recreational facilities include adult and family swimming pools, a full-service watersports center, and tennis courts, ensuring endless fun and social interactions. Embrace the energetic atmosphere that promises unforgettable evenings filled with laughter and excitement.

best hotels in Islamorada, USA
8.1
607 reviews
From $254

Dive into the vibrant nightlife at this beachfront resort, where the energetic atmosphere comes alive with fun activities and endless entertainment. Sip on custom cocktails at the lively Tiki Bar while enjoying live music that keeps the party going. Engage in beachside games or unwind by the outdoor pool, making every moment a chance to socialize and connect. Experience the excitement of Islamorada, where unexpected adventures await just outside your door.

best hotels in Islamorada, USA
8.3
339 reviews
From $240

Experience the vibrant nightlife at La Siesta Resort & Villas, where every evening comes alive with energy and excitement. Enjoy refreshing drinks and light bites at the on-site SIDECAR bar, the perfect spot to unwind after a day of thrilling activities like boating, jet skiing, and snorkeling. With the stunning backdrop of Islamorada's picturesque ocean, this resort offers an exhilarating atmosphere that invites guests to socialize and create unforgettable memories. Join us for an adventure-filled getaway!

best hotels in Islamorada, USA
8.7
1451 reviews
From $348

Dive into the vibrant nightlife of Islamorada with lively activities just moments away from your stay at Islander Resort. From exciting snorkeling excursions to thrilling deep-sea fishing adventures, the fun never ends. Unwind at the Beachside Bar and Grill for delicious cocktails and a festive atmosphere, or make a splash in one of the two on-site pools while soaking up the Florida sun. Experience the rich local culture and entertainment that awaits you outside your door.

best hotels in Islamorada, USA
8.4
26 reviews
From $649

Experience the vibrant nightlife and thrilling activities at this lively resort, where the fun never stops! Dive into exhilarating water sports like jet skiing or snorkeling, and explore the local scene with nearby nightlife that keeps the energy high. Whether you're looking to dance the night away or enjoy a refreshing cocktail by the pool, this energetic haven in Islamorada promises unforgettable nights filled with laughter and adventure. Join like-minded travelers and soak up the electric atmosphere!

Islamorada, USA Hotels with Spa

best hotels in Islamorada, USA
8.7
977 reviews
From $865

Rejuvenate your senses at the tranquil spa nestled within this coastal oasis in Islamorada. Offering signature treatments designed to promote wellness and relaxation, the spa provides a zen escape from everyday stresses. Relax in serene surroundings while indulging in therapeutic massages and rejuvenating facials. The calming atmosphere combined with expert care enhances your experience, creating a restorative journey that leaves you feeling refreshed and revitalized during your stay.

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