Find Hotels with an Outdoor Pool in Islamorada, FL

Discover top Islamorada attractions

Islamorada, Florida, offers a plethora of relaxing activities perfect for families seeking quality vacations. Start your day at the picturesque Founders Park, where you can stroll along the beach, enjoy a picnic, or let the kids splash in the tranquil waters of the pool. For the adventurous family, head to the Florida Keys Kayak Tours, where guided excursions through the mangroves allow you to spot local wildlife, providing a blend of excitement and serenity. Don’t miss the chance to visit the Theater of the Sea, where you can swim with dolphins or watch entertaining marine animal shows, an experience sure to delight both children and adults alike. Enjoy a leisurely afternoon at the Morada Way Arts and Cultural District, where local galleries and street art create a vibrant atmosphere, perfect for an afternoon of exploration and inspiration. Finally, indulge in fresh seafood at one of the waterfront restaurants, where dining with a view of the sunset seals the day with relaxation. For families looking for accommodations, the area around the Morada Bay Beach Café offers hotels with stunning pools that overlook the stunning ocean views, creating an inviting space to unwind after a day of exploration.

Find the best hotels with an outdoor pool in Islamorada

For travelers seeking a refreshing escape in Islamorada, Florida, these hotels feature inviting outdoor pools that promise relaxation and fun under the sun.

Sunset Inn

• Why it's great for poolside lounging: Sunset Inn stands out as a charming getaway for travelers who appreciate outdoor leisure, highlighted by its inviting outdoor pool and cabanas. With an excellent guest review rating of 9.4, this hotel provides a tranquil atmosphere perfect for relaxation in the sun.
• Other amenities: In addition to the pool, guests can take advantage of amenities such as a lovely garden area, free onsite bicycles, and daily housekeeping services. The inn also offers convenient self-parking options and kitchenettes in the rooms, providing a great balance of comfort and convenience for all visitors.
• Neighborhood: Matecumbe
• Nearby attractions: Matecumbe United Methodist Church - 0.53 miles, Islamorada Brewery & Distillery - 0.24 miles, Keys History & Discovery Center - 0.47 miles

Chesapeake Beach Resort

• Why it's great for poolside lounging: Chesapeake Beach Resort is a perfect choice for guests looking to enjoy the sun and surf with its fantastic outdoor pool facilities, receiving an impressive guest review rating of 9.2. The resort's outdoor pool, complete with sun loungers and accessible features, invites travelers to unwind after a day exploring the beautiful surroundings of Matecumbe.
• Other amenities: Beyond the pool, guests can enjoy complimentary breakfast daily, a private beach area, and a variety of onsite activities including boat tours and kayaking. The hotel also offers a kitchenette in the rooms, free parking, and daily housekeeping, ensuring a comfortable and convenient stay for all guests.
• Neighborhood: Matecumbe
• Nearby attractions: History of Diving Museum - 0.56 miles, Theater of the Sea - 1.08 miles, Windley Key Fossil Reef Geological State Park - 1.11 miles

Islander Resort

• Why it's great for poolside lounging: Islander Resort is an upscale destination for travelers looking for a vibrant outdoor pool experience, an impressive rating of 9.2 from guests. The resort features a stunning outdoor pool with cabanas and a poolside bar, making it an ideal spot for guests to soak up the sun and enjoy refreshing drinks throughout their stay.
• Other amenities: Additional amenities include direct beach access, complimentary bicycles, and a range of water sports activities available onsite. Guests can also enjoy a beachfront restaurant, fitness facilities, and concierge services, ensuring a luxurious and enjoyable experience in Matecumbe.
• Neighborhood: Matecumbe
• Nearby attractions: Matecumbe United Methodist Church - 0.53 miles, Islamorada Brewery & Distillery - 0.51 miles, Keys History & Discovery Center - 0.09 miles

Pines & Palms Resort

• Why it's great for poolside lounging: Pines & Palms Resort is a delightful choice for outdoor pool enthusiasts, earning a solid guest review rating of 9.2. This resort features a heated outdoor pool alongside a poolside bar, making it the perfect spot for guests to relax and socialize while enjoying the beautiful Florida weather.
• Other amenities: Guests can also take advantage of the resort's beachfront access, boat tours, and yoga classes. Additional offerings include complimentary beach towels, an onsite marina for water sports, and various dining options, ensuring a memorable stay for travelers looking to embrace the outdoors.
• Neighborhood: Matecumbe
• Nearby attractions: Bud n' Mary's Dive Center - 0.62 miles, Indian Key Historic State Park - 0.23 miles, Hurricane Monument - 1.0 miles

Cheeca Lodge & Spa

• Why it's great for poolside lounging: Cheeca Lodge & Spa presents an upscale retreat for travelers seeking outdoor pool relaxation, highlighted by its beautiful outdoor pool area and a high guest rating of 9.0. The resort features luxurious cabanas, a poolside bar, and an array of amenities that promote relaxation and leisure.
• Other amenities: In addition to the outdoor pool, guests can enjoy a hot tub, a full-service spa, and multiple dining options with ocean views. The resort also offers complimentary beach access, fitness classes, and various water sports activities, making it a premier destination for those looking to indulge in both relaxation and adventure.
• Neighborhood: Matecumbe
• Nearby attractions: Matecumbe United Methodist Church - 0.06 miles, Florida Keys Brewing Co. - 0.28 miles, MoradaWay Arts & Cultural District - 0.34 miles