The 30 Best Guest houses in Islamorada, Florida

The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida. This stunning property offers amazing ocean views, a sandy beach, pool, and an observation pier perfect for watching sunrises and sunsets. As a real estate and travel agency, The Beach House provides top-notch amenities and furnishings to ensure a relaxing and memorable vacation experience for all guests. Whether you're looking for a peaceful retreat or a fun-filled getaway, The Beach House at Tarpon Point is the perfect destination for your next trip to the beautiful Florida Keys.

Keys Ocean House is a charming lodging establishment located at 76311 Overseas Highway in the picturesque town of Islamorada, Florida. This quaint and cozy inn offers guests a peaceful and relaxing stay right by the ocean. The rooms are tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning views of the ocean from their rooms or take a leisurely stroll along the beach. The friendly staff is always ready to assist with any requests or recommendations for activities in the area. Whether you're looking for a romantic getaway or a family vacation, Keys Ocean House is the perfect choice for a memorable stay in the Florida Keys.

Islamorada Vacation Rental is a premier lodging option located at 101 Leoni Drive in Islamorada, Florida. As a combination of a real estate agency and travel agency, we specialize in providing top-quality vacation rentals for visitors looking to experience the beauty and charm of the Florida Keys. Our properties offer a range of amenities and locations, ensuring that guests have a comfortable and memorable stay. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious waterfront home, Islamorada Vacation Rental has the perfect option for you. Book with us today and start planning your dream vacation in paradise.

Nautical Tiki Cruises in Islamorada, Florida, offers a unique and exciting way to explore the stunning turquoise waters of the Islamorada Islands. Cruise on a floating tiki bar with your favorite music playing and your choice of beverages in hand. With 6-passenger tiki boats equipped with onboard restrooms and catamaran hulls for a safe and smooth ride, you can relax and enjoy paradise in style. Choose from a variety of cruise options, ranging from 90-minute day cruises to 6-hour excursions. Whether you want to kick back and soak up the sun or host a tiki party at the famous Islamorada sandbar, Nautical Tiki Cruises has got you covered. Individual tickets and private charters are available at affordable prices.

Casa Rio Islamorada is a charming lodging institution located at 121 Sapodilla Drive in Islamorada, Florida. Nestled in the heart of the Florida Keys, this cozy retreat offers a peaceful and serene atmosphere for guests to relax and unwind. With comfortable accommodations and a welcoming staff, Casa Rio Islamorada is the perfect place to escape the hustle and bustle of everyday life. Whether you're looking for a romantic getaway or a family vacation, this hidden gem is sure to provide a memorable experience. Explore the beautiful surroundings, soak up the sun on the nearby beaches, or simply enjoy a leisurely stroll along the waterfront. Come and experience the laid-back charm of Casa Rio Islamorada for yourself.

Located at 96 Madeira Road in Islamorada, Florida, Lorelei Restaurant & Cabana Bar is a popular spot for locals and tourists alike. With a laid-back and casual vibe, this institution offers a perfect setting to enjoy delicious food, refreshing drinks, and live music by local cover band Uncle Rico. The Sunset Celebration, featuring happy hour specials and stunning views of Florida Bay, is a highlight for many guests. Whether arriving by boat, car, or foot, visitors can relax and unwind while taking in the beautiful sunset. The on-site retail store offers a variety of items, including the popular Copper Line BBQ sauces. With a reputation for great value, amazing views, and fresh seafood, Lorelei is a must-visit destination in the Florida Keys. Join us for a memorable experience at Lorelei Restaurant & Cabana Bar.

Morada Bay is a charming waterfront restaurant located at 81600 Overseas Highway in Islamorada, Florida. This institution offers a unique dining experience with stunning views of the bay and a laid-back atmosphere. Guests can enjoy delicious food and cocktails while soaking in the beautiful surroundings. Whether you're looking for a romantic dinner, a casual lunch with friends, or a special event venue, Morada Bay has something for everyone. Come and experience the flavors of Florida at this must-visit restaurant in the United States.

Chef Michael's, located at 81671 Overseas Highway in Islamorada, Florida, is a renowned restaurant offering a unique dining experience. With chefs who have honed their skills in top restaurants around the world, Chef Michael's presents a culinary vision that is sure to impress you and your guests. Our dedicated wait and bar staff are committed to ensuring that you have a fantastic dining experience. In addition to our restaurant, Chef Michael's also offers off-premise catering services for a variety of events, including private parties, weddings, business lunches, and more. We take pride in sourcing our ingredients from local waters and farms, supporting sustainable practices and serving the freshest, highest quality dishes.

Hungry Tarpon Restaurant is a vibrant waterfront bar and restaurant located at 77522 Overseas Highway in Islamorada, Florida. This institution offers a delicious escape with a menu featuring the ocean's bounty, including signature dishes like Tuna Sliders, Mahi Reuben, and Pan Seared Salmon. Guests can enjoy their meals while watching the sun rise and feeding the Tarpon in the distance. In addition to mouthwatering seafood options, Hungry Tarpon Restaurant also offers a variety of cocktails, including the famous Trailer Trash Bloody Mary. The menu includes a range of options from breakfast items like glazed donut French toast to seafood dishes like blackened shrimp tacos and lobster mac and cheese.

Pierre's Restaurant is a unique and elegant establishment located at 81600 Overseas Highway in Islamorada, Florida. The exterior of the two-story building is reminiscent of old colonial residences in West Africa, while the interior showcases a blend of different cultures from around the world. The restaurant boasts a sparkling white facade facing the Florida Bay, offering stunning views of sunsets. The Green Flash Lounge on the ground floor features a beautiful mahogany bar, leather sofas, beige banquettes, and rattan chairs. The dark planked wood floors, Indian arcade, and Moroccan, Indian, and African artifacts add to the ambiance of the dining room and lounge.

Meze Morada is a charming restaurant located at 80925 Overseas Highway in Islamorada, Florida. Known for its delectable Mediterranean cuisine, this institution offers a unique dining experience with a variety of flavorful dishes inspired by the rich flavors of the region. Guests can enjoy a relaxing ambiance and attentive service while indulging in a selection of mezes, salads, grilled meats, and seafood. Whether you're looking for a casual lunch or a special dinner, Meze Morada is the perfect spot to savor delicious food in a beautiful setting.

Kaiyo Grill & Sushi is a premier dining destination located in Islamorada, Florida. Situated at 81701 Old Highway, this restaurant offers a unique and diverse menu featuring a fusion of Japanese and Caribbean flavors. Guests can enjoy fresh sushi, sashimi, and a variety of grilled seafood dishes in a stylish and upscale setting. With its waterfront location and breathtaking views, Kaiyo Grill & Sushi provides a memorable dining experience for locals and tourists alike. Come and indulge in delicious cuisine at this must-visit restaurant in the heart of the Florida Keys.

Nikai Sushi is a top-rated Japanese restaurant located at 81801 Overseas Highway in Islamorada, Florida. Known for serving the best sushi and Japanese cuisine in Islamorada, Nikai offers a wide variety of traditional favorites as well as innovative new dishes. The menu includes nigiri, sashimi, specialty rolls, and other delicious Japanese-inspired dishes. The chefs at Nikai use fresh, locally sourced ingredients to create a unique dining experience that combines the flavors of the Far East with the tropical vibes of the Florida Keys. In addition to their exceptional food, Nikai also offers a creative bar program featuring sake, craft cocktails, and beers. Guests can enjoy dishes like tuna with scallion and eel sauce, crispy wonton chips, and a variety of sushi and sashimi options. For those looking to try a bit of everything, Nikai offers a Chef's Tasting Menu with multiple courses featuring seasonal seafood and produce. The restaurant also has a selection of delicious desserts and a wide range of sake options for guests to enjoy. Whether you're a sushi lover or just looking to try something new, Nikai Sushi is the perfect place to experience the best of Japanese cuisine in Islamorada.

Sunset Lounge is a cozy and inviting restaurant located at 80460 Overseas Highway in Islamorada, Florida. With stunning views of the sunset over the water, this establishment offers a relaxed atmosphere where guests can enjoy delicious food and drinks. Whether you're looking for a romantic dinner for two or a casual meal with friends, Sunset Lounge is the perfect spot to unwind and savor the flavors of the Florida Keys. Come experience the laid-back charm and mouthwatering cuisine that make Sunset Lounge a must-visit destination in Islamorada.

Marker 88 is a popular bar and restaurant located at 88000 Overseas Highway in Islamorada, Florida. Known for its delicious food and refreshing drinks, Marker 88 offers a unique dining experience with stunning views of the ocean. In addition to their mouth-watering dishes, Marker 88 also has a boutique where guests can purchase souvenirs such as t-shirts, hats, craft sodas, and their famous key lime pie. Forgot to pick up a souvenir during your visit? Don't worry, you can shop online and have it shipped to you. Make your trip to the Florida Keys unforgettable with a visit to Marker 88.

Tides Beachside Bar & Grill is a charming waterfront restaurant located in Islamorada, Florida. Situated at 82100 Overseas Highway, this establishment offers a relaxed and casual dining experience with stunning views of the ocean. Guests can enjoy a delicious menu featuring fresh seafood, grilled meats, and refreshing cocktails. Whether you're looking for a romantic dinner by the water or a fun lunch with friends, Tides Beachside Bar & Grill is the perfect spot to unwind and savor the flavors of Florida.

The Oceanview Inn & Sports Pub is a charming establishment located at 84500 Overseas Highway in Islamorada, Florida. This institution offers a unique combination of bar, food, and lodging, making it the perfect destination for a Keys vacation. The guest rooms at The Oceanview Inn & Pub are clean, comfortable, and have a tropical flair, providing guests with a relaxing and enjoyable stay. Whether you're visiting for a weekend getaway or a longer stay, this inn has everything you need for a perfect vacation.

Located at 81801 Overseas Highway in Islamorada, Florida, Cheeca Lodge & Spa offers a luxurious retreat surrounded by turquoise waters, towering palms, and calm breezes. This oceanfront resort invites guests to experience barefoot luxury and embrace the laid-back lifestyle of the Florida Keys. With a range of thrilling activities, luxurious accommodations, exceptional dining options, and unparalleled relaxation, Cheeca Lodge & Spa promises an unforgettable getaway. Whether you're looking to celebrate love with a picturesque oceanfront wedding or host a productive corporate retreat, Cheeca Lodge & Spa offers the perfect venue. With over 15,000 square feet of meeting space, impeccable service from event planners, and a stunning backdrop of the Atlantic ocean, this resort is ideal for weddings, sales meetings, conferences, and more.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes. Experience authentic Keys life with island-inspired flavors and legendary cocktails while enjoying stunning sea views. The resort features lush private beaches, pools with ocean views, and fishing charters for the catch of your dreams. Accommodations include suites, cottages, and villas with idyllic Islamorada views and unique resort amenities. Special offers include discounts for Florida and Georgia residents, military personnel, and tax season rewards. Enjoy dining at Wild & Lime and nearby restaurants, as well as unforgettable experiences for special occasions. Plan your dream destination wedding or arrive at the Florida Keys marina for a seamless vacation experience. Explore all that La Siesta Resort & Villas has to offer and make memories to last a lifetime.

Drop Anchor Resort & Marina is a charming lodging establishment located at 84959 Overseas Highway in the beautiful Islamorada, Florida. This waterfront resort offers a serene and relaxing escape for guests looking to unwind and enjoy the stunning views of the Florida Keys. With comfortable accommodations, a marina for boat enthusiasts, and a range of amenities including a pool and beach access, Drop Anchor Resort & Marina is the perfect destination for a memorable vacation in the heart of the Keys.

KeysCaribbean Resorts is a premier lodging institution located at 97501 Overseas Highway in Key Largo, Florida, United States. Our team of professional agents is available 24 hours a day to ensure a stress-free and exceptional vacation experience for our guests. Choose from our select rentals at premier Upper & Middle Keys resort communities, where you'll have exclusive access to top-notch amenities such as private swimming pools, boat dockage, Jacuzzi tubs, and more. Whether you're planning a family reunion or a getaway with friends, we can accommodate your needs with our range of rental options.

Nestled in the picturesque town of Islamorada, Florida, Treasure Harbor is a charming lodging institution located at 200 Treasure Harbor Drive. Offering a tranquil and relaxing atmosphere, this hidden gem is the perfect destination for those seeking a peaceful getaway in the heart of the Florida Keys. With comfortable accommodations, stunning views of the harbor, and a range of amenities, including a pool and on-site restaurant, Treasure Harbor provides guests with a truly unforgettable experience. Whether you're looking to unwind by the water or explore the local attractions, Treasure Harbor is the ideal choice for your next vacation.

Casa Morada is a luxurious boutique lodging located on a quiet side road in Islamorada, Florida. Our property features 16 suites spread across two guest houses, the Garden House and the Seaview House. Guests can enjoy complimentary breakfast, use of kayaks, paddle boards, and bicycles, as well as yoga sessions on select days. Conveniently situated between Miami and Key West, Casa Morada is easily accessible by car or boat. We are a pet-friendly establishment and welcome children aged 16 and older. Each suite is uniquely designed and offers a range of amenities, from private terraces and soaking tubs to panoramic views of the water and private island.

The Caribbean Resort, located at 117 Carroll Street in Islamorada, Florida, is a charming lodging option that offers a taste of the Caribbean right in the heart of the United States. With its tropical-inspired decor, lush gardens, and stunning ocean views, this resort is the perfect escape for those looking to relax and unwind in a beautiful setting. Whether you're lounging by the pool, enjoying a cocktail at the beachside bar, or exploring the nearby attractions, The Caribbean Resort provides a tranquil and luxurious retreat for guests seeking a slice of paradise.

Coral Bay Resort, located at 75690 Overseas Highway in Islamorada, Florida, offers a relaxing and picturesque lodging experience. Guests can unwind in the fresh water heated pool after a day of exploring the waters. The resort grounds are beautifully landscaped with hibiscus and native Keys Palms, leading to a sandy beach that gently slopes into the crystal clear Gulf of Mexico. The sunsets are always stunning, and the waters beyond the dock are illuminated at night for guests to enjoy the marine life. Boaters are welcome to bring their boats, with no additional charges for boat dock and private ramp use, as well as ample trailer storage on site. Guests can relax under the illuminated tiki and enjoy the peaceful bay views in the evening.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean. The resort is designed as a peaceful tropical village, with oceanfront cottages and suites for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle that embodies the essence of Keys life. The resort boasts an oceanfront climate-controlled pool for relaxation, as well as seasonal yoga classes for rejuvenation. With personalized service and genuine hospitality, guests are welcomed as family at Pines and Palms Resort. Visitors can take advantage of complimentary kayaks, paddle boards, and bike rentals, as well as sunset sails and private fishing charters for added adventure.

Anglers Reef Villas is a luxurious waterfront lodging option located at 110 Anglers Way in Islamorada, Florida. As a combination of a lodging, real estate, and travel agency, Anglers Reef Villas offers guests the opportunity to experience the ultimate vacation in paradise. With stunning views of the ocean, top-notch amenities, and a prime location near popular attractions, Anglers Reef Villas is the perfect choice for those seeking a memorable stay in the Florida Keys. Whether you're looking to relax on the beach, explore the local area, or invest in a vacation home, Anglers Reef Villas has everything you need for a truly unforgettable experience.

Islander Bayside Villas is a charming lodging institution situated at 81450 Overseas Highway in the picturesque town of Islamorada, Florida. Nestled along the beautiful bayside, this tranquil retreat offers guests a peaceful and relaxing atmosphere with stunning views of the water. The villas are tastefully decorated and equipped with modern amenities to ensure a comfortable stay for visitors. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Islander Bayside Villas provides the perfect escape in the heart of the Florida Keys.

The Moorings Village is a charming lodging institution located at 123 Beach Road in Islamorada, Florida, United States. Nestled in a picturesque seaside setting, this luxurious retreat offers guests a tranquil and rejuvenating escape from the hustle and bustle of everyday life. With its beautifully appointed accommodations, lush tropical gardens, and pristine white sandy beaches, The Moorings Village provides the perfect backdrop for a relaxing vacation or romantic getaway. Whether you are seeking a peaceful retreat or an adventurous beach vacation, The Moorings Village offers a unique and unforgettable experience for all who visit.

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys. The resort features spacious and well-appointed rooms, a sparkling swimming pool, and stunning views of the surrounding landscape. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Topsiders Resort is the perfect destination for your next trip to paradise. With its convenient location and top-notch amenities, this resort is sure to provide a memorable and enjoyable experience for all guests.