Find Hotels with a Pool in Islamorada, FL from CA $226

The Caribbean Resort in Islamorada is a charming 3.5-star hotel that boasts an impressive outdoor pool, great for families seeking relaxation and fun. Guests rave about the beautiful and clean rooms, as well as the helpful staff who go above and beyond to ensure a great stay. With ocean views and easy access to nearby beaches, this resort offers a delightful blend of comfort and convenience.Another fantastic option is the Sunset Inn, a cozy 3-star hotel known for its warm outdoor pool and spacious rooms. Travellers appreciate the friendly and helpful staff, as well as the central location that makes exploring Islamorada a breeze. With free bicycle rentals and self-parking, it's an excellent value for families wanting to make the most of their adventure.For a more upscale experience, consider Casa Morada, also a 3.5-star hotel, which features an inviting outdoor pool alongside a poolside bar. Guests enjoy complimentary breakfast and praise the excellent reception and helpful staff. The comfortable rooms and good facilities make it a popular choice among travellers who value quality.Chesapeake Beach Resort, another 3.5-star gem, offers a clean and well-maintained outdoor pool, along with friendly service and a beautiful location. Guests love the complimentary breakfast and the comfortable, clean rooms that enhance their stay in this picturesque destination.Lastly, for those looking for a luxurious escape, Cheeca Lodge & Spa stands out with its stunning outdoor pool and resort-style amenities. This 5-star hotel features a poolside bar, cabanas, and even private beach access, ensuring a lavish experience. Guests frequently highlight the exceptional service, beautiful accommodations, and delicious food, making it a top choice for those wishing to indulge during their family getaway.

Cheeca Lodge & Spa is a stunning 5-star retreat in Islamorada that offers an exceptional experience for travellers seeking luxury and privacy. With its private outdoor pools, guests can enjoy a serene atmosphere, lounging in poolside cabanas or taking a refreshing dip while savoring the beautiful surroundings.This resort is highly rated, boasting a traveller review score of 9.2, and it's no surprise why. Guests rave about the friendly and amazing staff, the beautiful and clean rooms, and the overall excellent service. The amenities are designed for relaxation and indulgence, featuring options like a private hot tub, deep-soaking bathtubs, and even massages on the beach for those looking to unwind.In addition to the luxurious pools, Cheeca Lodge & Spa provides a range of activities, including onsite tennis and golf, ensuring that families and couples alike can find something to enjoy. The beachfront restaurant offers delicious dining options, superb for a sunset meal after a day filled with adventure.

The Caribbean Resort is a delightful 3.5-star hotel that offers an unforgettable stay with its outdoor pool and breathtaking ocean views. Guests have praised the staff for being incredibly helpful, while the rooms are noted for their beautiful and clean designs. The resort features convenient amenities like pool sun loungers and easy access for those with mobility needs, making it a wonderful option for families seeking both relaxation and adventure.For those looking for a mix of comfort and great service, the Chesapeake Beach Resort, also rated at 3.5 stars, is another excellent choice. Its outdoor pool is well-maintained, and the complimentary continental breakfast is a hit among travellers, who describe the staff as friendly and the location as beautifully scenic. The resort boasts lovely beach views, creating an inclusive setting for families wanting to soak up the sun.If luxury is on your agenda, Cheeca Lodge & Spa stands out as a 5-star gem. It features a stunning outdoor pool surrounded by cabanas, a poolside bar, and a private beach area, making it great for those who enjoy upscale relaxation. Guests rave about the friendly and amazing staff, coupled with the beautifully clean rooms and excellent dining options, ensuring a memorable experience for everyone.For a more laid-back vibe, the Islander Resort, rated 4 stars, provides an inviting outdoor pool, poolside bar, and stunning beach views. Families will appreciate the spacious rooms and the attentive service, which travellers have highlighted as both friendly and accommodating.Lastly, the Pines & Palms Resort offers a cozy atmosphere with its outdoor pool and beautiful ocean views, great for families looking to enjoy a peaceful retreat. With clean rooms and a welcoming location, it's an ideal spot to unwind after a day of adventure in the scenic surroundings of Islamorada.

The Cheeca Lodge & Spa is a luxurious 5-star retreat in Islamorada that offers an exquisite experience with its outdoor pool, complete with inviting cabanas and sun loungers. Guests rave about the stunning amenities and exceptional service, making it a top choice for those seeking relaxation and adventure alike.Another excellent option is the Islander Resort, rated 9.2 by travellers. This 4-star hotel features spacious outdoor pool cabanas and sun loungers, great for families looking to unwind after a day of exploring. The pool area is described as beautiful and expansive, providing a serene atmosphere for both adults and children.For those seeking a charming stay, the Sunset Inn offers a cozy 3-star experience. With free pool cabanas and a warm, welcoming pool environment, this hotel boasts a stellar review rating of 9.4, where guests appreciate the cleanliness and helpful staff.Lastly, Casa Morada, a 3.5-star hotel, offers resort-inclusive amenities including outdoor pool sun loungers and a poolside bar, ensuring a delightful day in the sun. With a rating of 9.4, guests praise the comfort of the rooms and the excellent reception service.

Casa Morada is a charming 3.5-star hotel that offers an inviting outdoor pool experience alongside a delightful poolside bar. Guests have praised the hotel for its comfortable and excellent rooms, along with the helpful staff that make your stay even more enjoyable. With a traveller review score of 9.4, it's clear that visitors appreciate the quality of service and amenities available.Another top choice is the luxurious Cheeca Lodge & Spa, a 5-star gem that features an expansive outdoor pool, complete with poolside cabanas and a bar serving refreshing drinks. Guests rave about the beautiful and clean rooms, as well as the amazing service provided by the friendly staff. With a stellar review score of 9.2, this hotel not only caters to your relaxation needs but also offers a range of amenities, including a beachfront restaurant and spa services.For a well-rounded stay, the Islander Resort stands out with its outdoor pool and poolside bar, superb for cooling off and enjoying a drink in the sun. Rated at 9.2, guests love the beautiful and spacious pool area, along with the friendly staff that enhance the overall experience.If you're looking for a more intimate setting, consider the Pines & Palms Resort, a 3-star option that also provides an inviting outdoor pool with a poolside bar. With a review score of 9.2, it's noted for its beautiful location and clean rooms, making it a cozy retreat for families and couples alike.Lastly, Amara Cay Resort, a 4-star hotel, features a lovely outdoor pool with poolside service for food and drinks. Guests have appreciated the beautiful location and comfortable accommodations, giving it a rating of 8.8. The friendly staff and the beachside restaurant add to the hotel's appeal, ensuring a delightful experience during your stay in Islamorada.

The Caribbean Resort in Islamorada offers a delightful experience for travellers, featuring a stunning outdoor pool that promises relaxation and enjoyment. With a great review score of 10.0, guests rave about the helpful staff and beautiful, clean rooms, making it an ideal choice for those seeking quality and convenience.Just a short distance from the MoradaWay Arts & Cultural District, the Sunset Inn is another fantastic option. This 3-star hotel boasts a warm outdoor pool and spacious, clean rooms. Rated at 9.4, travellers appreciate the friendly service and excellent central location, along with free bicycle rentals that make exploring the area even easier.For a more upscale experience, Casa Morada, also rated 9.4, provides a resort-style outdoor pool complemented by a poolside bar and free breakfast options. Guests love the comfortable accommodations and attentive staff, making it a great spot for families looking to unwind after a day of adventure.Finally, if you're in search of a luxurious retreat, Cheeca Lodge & Spa stands out with its expansive outdoor pool, poolside cabanas, and a host of amenities including a beachfront restaurant and a wellness spa. With a rating of 9.2, it's renowned for its exceptional service and beautiful surroundings, creating a memorable getaway for those who wish to indulge.

Islamorada, Florida, is a tropical paradise famed for its stunning beaches and crystal-clear waters, making it a fantastic destination for those seeking relaxation and adventure alike. Notably, several hotels in this charming area offer inviting outdoor pools that enhance the guest experience with a blend of leisure and excitement.For families looking for a fun-filled getaway, the Cheeca Lodge & Spa stands out with its luxurious family pool area, complemented by a full-service watersports facility nearby. This allows for a mix of poolside relaxation and thrilling aquatic adventures, ensuring there's something for everyone. The option to reserve private cabanas by the spa pool or infinity pool adds an extra touch of luxury, superb for parents wanting a serene escape while kids enjoy the water.Couples seeking a romantic retreat will love the Chesapeake Beach Resort, which features two outdoor pools with breathtaking ocean views. The resort's oceanfront event venue creates opportunities for intimate gatherings or sunset celebrations, providing a picturesque backdrop for unforgettable moments together.For those who appreciate a more laid-back atmosphere, the Fisher Inn Resort & Marina offers an outdoor heated pool surrounded by sun loungers and outdoor furniture. This setting is ideal for leisurely days spent soaking up the sun, with easy access to the beach for a refreshing dip in the ocean.With a variety of hotels that blend outdoor pool activities with great experiences, Islamorada promises a delightful stay for all types of travellers.