Find Hotels with a Pool in Islamorada, FL

Cheeca Lodge & Spa is a stunning 5-star hotel located in the heart of Islamorada, offering an array of luxurious amenities that cater to travellers seeking both adventure and relaxation. With an impressive review score of 9.2, guests rave about the friendly and attentive staff, the beautiful and clean rooms, and the exceptional dining experiences.One of the standout features of Cheeca Lodge is its private outdoor pool, which provides an exclusive retreat for guests looking to unwind. This serene environment is complemented by poolside cabanas and sun loungers, ensuring you can soak up the sun in style. Additionally, the resort's beachfront location allows for easy access to a private beach, making it superb for families and couples alike.Whether you're enjoying a massage on the beach, indulging in 24-hour room service, or taking advantage of the resort's on-site tennis and golf facilities, Cheeca Lodge & Spa seamlessly blends luxury with the natural beauty of Florida.

The Caribbean Resort is a charming 3.5-star hotel that captivates guests with its stunning ocean views and an inviting outdoor pool, rated a great 10.0 by travellers. Families appreciate the helpful staff and beautifully clean rooms, making it a wonderful choice for those seeking both relaxation and adventure in Islamorada.Another fantastic option is the Chesapeake Beach Resort, also rated 3.5 stars and earning an excellent score of 9.2. This hotel not only features a clean outdoor pool but also offers beautiful views of both the ocean and the beach. Guests rave about the friendly staff, comfortable rooms, and excellent complimentary breakfast, making it an ideal family getaway.For a luxurious experience, consider the 5-star Cheeca Lodge & Spa, where you'll find an expansive outdoor pool along with private cabanas for a touch of elegance. With a review rating of 9.2, this resort is great for families looking to indulge. Guests praise the amazing amenities, beautiful rooms, and excellent dining options, ensuring a memorable stay for everyone.The Pines & Palms Resort, a 3-star hotel with a cozy atmosphere, also boasts an outdoor pool with ocean views, rated at 9.2 by visitors. Families enjoy the beautiful location and clean rooms, great for unwinding after a day of adventure.Lastly, the Islander Resort stands out with its 4-star rating and beautiful outdoor pool, accompanied by breathtaking ocean and beach views. With a score of 9.2, guests highlight the friendly staff and spacious, clean accommodations, making it an excellent choice for families seeking both adventure and comfort.

The Cheeca Lodge & Spa is a renowned 5-star hotel in Islamorada, celebrated for its stunning outdoor pool area, complete with luxurious cabanas and sun loungers. Guests rave about the exceptional service, beautiful accommodations, and the serene atmosphere that makes it a great retreat for families and couples alike, earning it an impressive traveller rating of 9.2.For a more casual vibe, the Sunset Inn, a charming 3-star option, offers an inviting outdoor pool with complimentary pool cabanas. Travellers appreciate its central location and friendly, helpful staff, making it a great choice for those seeking a warm and welcoming environment, reflected in its stellar review score of 9.4.Another fantastic option is the Islander Resort, a 4-star property featuring both pool cabanas and sun loungers by the pool, which is described as beautiful and spacious. Guests enjoy the incredible service and well-kept facilities, securing a traveller rating of 9.2.Lastly, Casa Morada, a 3.5-star hotel, boasts a lovely outdoor pool where you can relax on sun loungers, complemented by a poolside bar and complimentary breakfast options. With a review score of 9.4, this hotel is known for its excellent staff and comfortable accommodations, great for families seeking both fun and relaxation.

Casa Morada, a charming 3.5-star hotel, offers a delightful poolside bar that enhances your relaxation by serving refreshing drinks while you soak up the sun. Guests consistently rave about the comfortable rooms and the excellent service from the helpful staff, making it a top choice for those seeking a tranquil escape.For a bit of luxury, Cheeca Lodge & Spa stands out as a 5-star gem in Islamorada. Not only does it feature an inviting poolside bar, but it also boasts private cabanas and a stunning beachfront location. With a stellar rating of 9.2, visitors appreciate the beautiful clean rooms and the friendly, attentive staff who go above and beyond to ensure a memorable stay.Another great option is the Pines & Palms Resort, rated 9.2 by travellers. This 3-star resort also provides a poolside bar, allowing guests to enjoy snacks and beverages as they lounge by the outdoor pool. The beautiful surroundings and clean accommodations make it a lovely spot for travellers.Islander Resort, a 4-star hotel, also features a poolside bar, where you can indulge in drinks while enjoying the beautiful ocean view. Guests frequently compliment the friendly service and the spacious, well-maintained pool area, contributing to a great family-friendly atmosphere.Lastly, Amara Cay Resort, with an 8.8 rating, offers a welcoming poolside bar as well. Known for its beautiful outdoor pool and comfortable rooms, this 4-star resort provides a relaxing environment superb for unwinding after a day of exploration.

The Caribbean Resort is a charming 3.5-star hotel that features an inviting outdoor pool, great for families looking to unwind after a day of exploring. Guests rave about the beautiful, clean rooms and the helpful staff, earning this hotel a stellar rating of 10.0. Located nearby MoradaWay Arts & Cultural District, it provides easy access to local art and culture, making it an ideal choice for those who appreciate both leisure and exploration.Another excellent option is the Sunset Inn, a cozy 3-star hotel boasting a warm outdoor pool and spacious, clean rooms. With a review rating of 9.4, travellers appreciate the friendly staff and the central location, which is great for venturing out to nearby attractions. Plus, the complimentary self-parking adds to the convenience for families traveling by car.For a more upscale experience, Casa Morada, also a 3.5-star hotel, offers a resort-style outdoor pool along with free continental breakfast. Guests have praised the excellent and comfortable rooms, as well as the attentive staff, securing a review score of 9.4. Its proximity to the cultural district makes it a wonderful base for exploring the local art scene.Lastly, if you're seeking a luxurious stay, consider Cheeca Lodge & Spa, a stunning 5-star resort that features a spectacular outdoor pool, private beach access, and a range of amenities including a poolside bar and tennis courts. With a review score of 9.2, guests consistently highlight the friendly service, beautiful accommodations, and delicious food, ensuring a memorable family getaway.

Islamorada, known as the "Sport Fishing Capital of the World," is an idyllic destination that offers a variety of hotels with outdoor pool activities and events. This charming area is great for travellers looking to enjoy the sun, sea, and leisure in a tropical paradise.Chesapeake Beach Resort stands out with its two inviting outdoor pools that boast breathtaking ocean views, setting the stage for both relaxation and social gatherings. The resort also features an oceanfront event venue, allowing guests to enjoy poolside events while soaking up the stunning scenery.For families seeking a luxurious experience, Cheeca Lodge & Spa is an excellent choice. The resort offers a family-friendly pool area complete with a full-service watersports facility just a stone's throw away. Guests can reserve private cabanas at either the spa pool or infinity pool, creating a serene personal oasis where you can unwind and take in the beautiful surroundings.Fisher Inn Resort & Marina is another fantastic option, featuring a heated outdoor pool that caters to comfort and enjoyment. With poolside amenities, including sun loungers and outdoor furniture, this resort encourages guests to bask in the warm Florida sun while enjoying a leisurely day by the water.