Cool Places to Stay in Islamorada and the Middle Keys

The Islamorada and Middle Keys area of the Florida Keys is world-renowned for its fishing, diving, and sailing. But there’s so much more to this island paradise than just aquatic activities. The hotels and resorts in Islamorada offer some of the best accommodations in the Florida Keys, with amenities and views that are sure to please everyone, from budget-minded travelers to luxury vacationers these are some of our favorite places to stay in Islamorada.

Getting to Islamorada and the Middle Keys

Just as it sounds, the Middle Keys are in the middle of the Florida Keys. The island chain is connected by the Overseas Highway from Homestead, Florida to Key West. About halfway down is where you’ll come to the Middle Keys. This part of the Florida Keys is much more about getting on the water and having adventures than experiencing history and culture like you would in Key West.

Read up on the Towns of the Florida Keys!

The Middle Keys start at the Seven Mile Bridge and go to Upper Matacumbe Key. The primary islands in the Middle Keys include Duck Key, Fiesta Key, Pigeon Key (private), Long Key, Conch Key, Key Vaca, Boot Key, Craig Key, Fat Deer Key, Crawl Key, Knight’s Key, Long Point Key and Key Colony Beach. Islamorada is called the Village of Islands and is the incorporation of Lower Matacumbe Key through Plantation Key.

Marathon is also considered a part of the Middle Keys, but it’s also quite large and different, so we’ll cover it in a different article.

Take a quick peek at the Middle Keys if you like, that way you can get a feel for this aspect of planning a trip to the Florida Keys.

Top Picks for Cool Places to stay in Islamorada and the Middle Keys

Whether you’re looking for places to stay in Islamorada while fishing, diving in nearby Captain Hooks Marina, or simply want to relax in the sun during your stay in Islamorada, these properties are sure to meet your needs. Here are some of our favorites!

Budget-Friendly Places to Stay in Islamorada

La Jolla Resort

La Jolla Resort in Islamorada is a beachfront motel that overlooks the Islamorada Florida Keys. It comprises six colorful, retro-inspired buildings and is only 0.7 miles from the History of Diving Museum. The cottages and villas at La Jolla Resort are all brightly painted, 2-story buildings and feature functional contemporary interiors. Guests can enjoy plenty of amenities during their stay, including a heated outdoor pool, complimentary continental breakfast, and free WiFi. La Jolla also has a tour desk where guests can book excursions and activities around the area. With its convenient location and amenities, La Jolla Resort is the perfect place to stay for a fun and relaxing vacation in Islamorada.

Book Your Stay at the La Jolla Inn Here!

Coconut Cove Resort & Marina

Coconut Cove Resort & Marina is the perfect place to get away from it all and enjoy the beautiful Florida Keys. This oceanfront hotel is situated on a 7-acre nature preserve, making it the ideal spot for wildlife lovers. The rooms here are cozy and comfortable, with flat-screen TVs, minifridges, and microwaves. Each room is equipped with whirlpool tubs while relaxing with stunning views of the Florida Keys. Whether you’re trying to get away from the hustle and bustle of everyday life or want to explore all Islamorada offers, Coconut Cove Resort & Marina is the perfect place for you.

Book Your Stay at the Coconut Cove Marina Here!

The Key Lantern Blue Fin Inn

The Key Lantern Blue Fin Inn is a great place to stay for the Old Florida pricing. One of the lowest-priced motels in the Florida Keys and close to everything, the Key Lantern provides guests with complimentary parking, BBQ grills, and guest laundry facilities. The perfect place for a budget-friendly getaway, the Key Lantern is also within proximity to all the best that Islamorada has to offer.

Breezy Palms Resort

Breezy Palms Resort is a serene and beautiful oceanfront resort situated in Islamorada. The resort is perfect for those who want to relax and enjoy the stunning views of the ocean. It is also an awesome place for families because there are plenty of activities nearby, such as the Indian Key Historic State Park and the Theater of the Sea marine park. Breezy Palms Resort is a truly unique place that offers something for everyone. Whether you’re looking to explore the surrounding area, or sit back and relax, this resort is sure to please.

Book your Stay at the Breezy Palms Resort Here!

The Sunset Inn

The Sunset Inn in Islamorada is a casual inn situated close to marinas and restaurants. It is just a short drive from the Theater of the Sea marine park and Anne’s Beach. The inn offers an outdoor pool, sundeck, and complimentary parking for cars and boat trailers, making it the perfect spot for exploring all that this beautiful area has to offer.

Book your stay at the Sunset Inn Here!

Boutique Places to Stay in Islamorada

Drop Anchor Resort & Marina

Located in Islamorada, Drop Anchor Resort & Marina is a tropics-inspired hotel that offers airy rooms with free WiFi, minifridges and coffeemakers, flat-screen TVs, and either 1 or 2 bedrooms. Amenities at the resort include a boat ramp, a fishing pier, a heated oceanfront pool, direct beach access, and sitting areas shaded by thatched umbrellas. The resort is also unique because it offers an on-site marina for guests who want to explore the surrounding waters by boat.

Book your Stay at the Drop Anchor Inn Here!

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina in Islamorada is a 3-minute walk from Windley Key Fossil Reef Geological State Park and 9 minutes on foot to the marine park Theater of the Sea. Amenities include a freshwater pool, a sandy deck with sun loungers, a BBQ area, a boat ramp and a dock. Fisher Inn Resort & Marina is the perfect place to stay for those who want to explore the beauty of the Florida Keys. Fisher Inn offers stunning views of the Atlantic Ocean and easy access to all of the Keys’ attractions.

Book your stay at the Fisher Inn & Marina Here!

The Sands of Islamorada Hotel & Resort

The Sands of Islamorada Hotel & Resort is the perfect place to unwind and enjoy the beautiful Florida Keys. The hotel’s stunning oceanfront location offers incredible views and plenty of opportunities to relax and soak up the sun. The spacious outdoor pool is flanked by palm trees, making it the perfect spot to spend a day lounging with a book or cooling off after a swim. For those looking for a more active vacation, the hotel also offers boat and jet ski rentals and fishing and BBQ facilities. Whether you’re looking for a relaxing getaway or an adventure-filled holiday, the Sands of Islamorada Hotel & Resort has all that you need for an unforgettable trip.

Book your stay at the Sands of Islamorada Hotel & Resort Here!

Pines and Palms Resort

Pines and Palms Resort in Islamorada is the perfect place to relax and enjoy the beautiful Florida Keys. With its 12 buildings spaced across 5 acres, this low-key resort offers a heated oceanfront pool, tiki bar, sandy beach area with sun-loungers, fishing and swimming piers, and complimentary boat dockage. You can also avail bikes and kayaks to tour the area. The resort’s unique location, set along the ocean and shaded by palm trees, makes it a perfect location to enjoy the sunny Florida weather.

Book your stay at the Pines and Palms Resort Here!

Postcard Inn Beach Resort and Marina

Postcard Inn Beach Resort and Marina features four on-site bars/restaurants, including a beachfront bar with a Swiss Family Robinson-inspired theme serving light bites. There is also a buzzy Tiki cocktail bar for your enjoyment. Other amenities include a private beach, two pools, and a marina with boat slips and rentals. This is the perfect spot to relax and enjoy all Islamorada offers!

Book your Stay at the Postcard Inn Beach Resort and Marina Here!

Looking for a fabulous Florida Keys vacation spot and some of the best options for places to stay in Islamorada? Look no further. This vibrant coastal town is home to some of the best hotels and resorts in the area. It is the perfect destination for travelers and foodies alike. Whether you’re looking for a luxurious beachfront resort or a quaint bed and breakfast, Islamorada has something to offer everyone. Soak up the sun on world-famous beaches, explore miles of stunning coastline, and indulge in fresh seafood at some of the top-rated restaurants in Florida. If you’re searching for paradise, Islamorada is it!