For families looking for a Florida Keys getaway that combines relaxation, outdoor adventure, comfortable accommodations, and memorable dining, the Islamorada Resort Collection offers something especially convenient: three distinct oceanfront properties connected as one vacation experience.
During our recent visit, we had the opportunity to explore Three Waters Resort & Marina, Amara Cay Resort, and La Siesta Resort & Villas. Each property has its own personality, but guests can enjoy amenities across the entire collection, including five pools and beaches, multiple dining options, including five pools and private beaches, a rarity in the Florida Keys, activities, and transportation aboard the complimentary Rum Runner water taxi.
Three Waters Resort & Marina: The Center of the Action
Set across 15 oceanfront acres, Three Waters Resort & Marina is the largest and most activity-filled of the three properties. It is an appealing choice for families who enjoy having plenty to do without leaving the resort.
Children can enjoy the family-friendly pools, beaches, arcade, and scheduled activities, while parents can relax by the water or explore the marina. The resort also includes kayaks, paddleboards, and bicycles with each stay, making it easy for families to experience Islamorada beyond the pool deck.
Children can feed the tarpon from the marina, learn to fish like a local, play at the arcade while parents can relax by the pool or take a family trip to the Islamorada Sand Bar.
Accommodations include rooms, suites, and cottages, with options designed to provide additional space for families and groups. Many feature private balconies or patios overlooking the ocean, marina, or tropical grounds.
Dining is another highlight. Families can choose from casual poolside options, pizza, soft-serve treats, and waterfront dining, while parents may enjoy an elevated dinner at Kindler Wood-Fired Fare or seafood and shareable plates at Little Limón. The property is also home to the iconic Tiki Bar, connected to Islamorada’s history as the birthplace of the Rum Runner cocktail.
Three Waters also includes The Cove, an adults-only resort-within-a-resort. This allows the property to serve different types of travelers while keeping its main pools, beaches, activities, and accommodations welcoming for families.
Amara Cay Resort: Relaxed, Stylish and Family-Friendly
Amara Cay Resort offers a more intimate coastal atmosphere with modern island style, ocean views, and a relaxed poolside setting. It is a good fit for families who want an easygoing stay while still having access to activities across the full resort collection.
Families can enjoy the pool, beach areas and have dinner at ReelCatch where kids eat free on Tuesdays.
The outdoor spaces invite guests to slow down. Parents can relax by the pool or beneath the palms while children enjoy the open-air setting and water activities. Families interested in exploring more can board the Rum Runner or use the shuttle to visit sister properties.
Amara Cay also welcomes well-mannered dogs in designated accommodations, making it an option for families who prefer to bring a four-legged member of the household. Fees and room restrictions apply, so families should confirm the current policy before booking.
La Siesta Resort & Villas: Space to Slow Down and Reconnect
Colorful, quiet and residential in feeling, La Siesta Resort & Villas offers a different kind of family escape. The property features oceanfront suites, beach cottages, casitas, and private villas, giving families flexibility based on their group size and vacation style.
Many accommodations include separate living areas, sleeper sofas, kitchen conveniences, patios, or balconies. The standalone beachfront cottages sleep up to four guests, while the private villas offer additional room for extended families, celebrations, or multigenerational trips. Select villas also include personalized butler service and private dock access.
La Siesta feels peaceful and secluded, encouraging families to spend time outdoors together. Guests can swim, bike, kayak, paddleboard, fish, or simply relax near the shoreline. Its spacious grounds and home-style accommodations make it especially appealing for families who want less of a traditional hotel atmosphere and more of a private island retreat.
When families are ready for additional activities or dining, the Rum Runner provides a scenic ride to Amara Cay and Three Waters, weather permitting.
The Rum Runner: Part Transportation, Part Family Adventure
One of the collection’s most enjoyable features is the complimentary Rum Runner water taxi. Rather than driving between properties, guests can cruise across the water. The Rum runner also offer a Karaoke and Bayside Cruise as part of the experience.
Three Properties, One Flexible Family Vacation
The greatest advantage of the Islamorada Resort Collection is flexibility. Families can select the atmosphere that suits them best while still enjoying the broader collection.
Together, the three properties allow families to create their own version of an Islamorada vacation—whether that means pool time, kayaking, waterfront meals, fishing adventures, quiet mornings by the beach, or simply enjoying the Florida Keys at a more relaxed pace.
For more information or to book your stay at Islamorada Resort Collection visit www.islamoradaresortcollection.com
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