El Embajador isn't as historic and charming as the other two hotels on this list, but it gets the top spot due to its resort-like amenities that tick several essential boxes for a Caribbean getaway, like a lovely pool area, well-manicured grounds, a small casino, and multiple restaurants and bars. Despite these many features, the hotel feels cozier and more inviting than your typical mega-resort. Note that when we visited the hotel in 2015 we found the decor to seem regal at first but fading upon closer inspection. At the time, El Embajador was managed by Occidental Hotels; it has since become a Royal Hideaway Hotel and is currently undergoing renovations.

Once the personal home of Santo Domingo’s founder, this upscale hotel dates back to 1502, with many of its original fixtures, architecture, and decor intact. In fact, the buildings that house Hodelpa Nicolas de Ovando are a UNESCO World Heritage Site. Its atmosphere is quiet, relaxed, and sophisticated -- but not stuffy. The 97 rooms range from small to sprawling, but all include original, centuries-old design elements plus minibars, flat-screen TVs, free Wi-Fi, and Nespresso makers. The outdoor pool offers decent views of Rio Ozama and La Residence restaurant serves up fine French dining in one of the city’s most romantic alfresco dining spaces. 

Like Hodelpa Nicolas de Ovando, this property is steeped in history: before becoming a chic boutique hotel, it was a convent, an arsenal for the French army, a school, and a private residence. Its 24 rooms seamlessly blend modern design with original 17th-century architectural details and offer private outdoor spaces, free minibars, and high-tech amenities like flat-screen Smart HDTVs, Bang & Olufsen Wi-Fi radios, and bedside tablets for the 24-hour room service, and LCD panels for requesting housekeeping or laundry service. Free in-room minibars include juice, bottled water, and soft drinks. El Embajador has more resort-like features, but common areas here include a rooftop infinity pool with city views and poolside drink service, a restaurant with a courtyard, and a lobby bar with high-end cigars, wines, and single-malt whiskeys.