Islamorada Vacation Rentals With Pool

Our Islamorada vacation rentals with pools are made for long days by the water, with homes ranging from oceanfront villas with heated private pools to resort-style stays with access to pools, hot tubs and beach facilities. Selected retreats sit directly on the shoreline, combining swimming pools with private beaches, ocean-view terraces and boat docks, so you can move easily between pool time and the water.

Many of our Islamorada vacation rentals make outdoor living a big part of the stay. Across the collection you’ll find retreats with tiki bars, outdoor kitchens, BBQ areas, fire pits, hammocks and generous pool decks, while some larger vacation rentals offer optional hot tubs and games' rooms, making them ideal for year-round family and group getaways.

For something even closer to the coast, selected Islamorada rentals with pool included also feature direct beach access, for an exclusive Florida Keys stay. Spend the morning fishing, kayaking or exploring the Keys, before returning for an afternoon of swimming and evening relaxation.