PHOTO: Beachfront at the Caribe Hilton. (All photos by Brian Major)

Several hotel companies that offer more than one property in a city but it’s unquestionably rare to find one operating three distinct properties within a three-mile radius of one another in one of the world’s most tourism-intensive destinations. But the label fits for Hilton Worldwide Resorts in Puerto Rico.

In addition to its three properties in historic San Juan, Hilton Worldwide operates an exotic coastal property in Fajardo, giving the company four Puerto Rico properties, each with amenities and features that match the amazing diversity and broad range of attractions this highly popular destination offers.

Puerto Rico was one of only five Caribbean destinations to attract more than 1.3 million visitors in 2013, according to Caribbean Tourism Organization statistics.

On a recent visit, I spent a week exploring aspects of each Hilton Worldwide property to get a taste of what they offer and how one company can successfully position four properties in the same competitive destination.

Condado Plaza Hilton

The property: This classic property on Ashford Avenue, the main drag of the trendy Condado district, might be the most iconic hotel in San Juan, a city filled with them.

The Condado Plaza was designed in 1963 by Morris Lapidus, father of the neo-Baroque Miami Modern architectural school, and is the only hotel to overlook both the Atlantic Ocean and San Juan’s tranquil Condado Lagoon. The hotel received a tragic place in history in 1978 when high-wire walker Wallenda fell and died while attempting to walk between the hotel’s two 10-story, 121-foot high towers.  

Through the years the hotel has maintained an urbane appeal that continues to this day. The property’s 571 guest rooms and suites were recently revamped by designer Leo Daly with brilliantly executed, contemporary interiors that include private balconies with sweeping views of the ocean and the cosmopolitan downtown district.

There are eight restaurants and bars including celebrity chef Wilo Benet’s flagship eatery; a private beach with a protected swimming area; three outdoor swimming pools and a 12,500 square foot casino. For travel consultants working with groups, the property provides 40,000 square feet of meeting space including ocean-side rooms and facilities.

What makes it special: San Juan’s lobby bar scene is as much about trendy people-watching as anything else, and at the top of the pyramid is the Condado’s lobby bar, a masterpiece of the Lapidus style which came to define beachfront resort design. Cool and brilliant blue and pink colors contract with while marble floors and white leather bar stools to create an irresistible, space-age atmosphere. The bar is among the most popular evening spots in the entire city, and on weekends is routinely crowded with visitors and locals alike.

Caribe Hilton

The property: The Caribe Hilton is another San Juan landmark, the first property Hilton Hotels ever operated outside of the continental United States. Guests at the December 1949 opening included Gloria Swanson and Eddie Rickenbacker, and the hotel is said to be the birthplace of the Pina Colada, created by bartender Ramon “Monchito” Marrero, who first served his original mixture of rum, coconut cream, and pineapple juice in 1954.

The property is set amongst 17 acres of lush tropical gardens and is the city’s largest hotel with 917 rooms including deluxe suites and the Condado Lagoon Villas, which feature ocean and garden views. The resort offers an outstanding array of dining options, from a Morton’s Steakhouse to Lemongrass, which offers pan-Asian Latino cuisine. In addition to a main lobby Starbucks outlet, the resort operates what is said to be the only beachside Starbucks store.

What makes it special: The Caribe Hilton’s secluded beach and oceanfront swimming pools set a high standard among the district’s similar offerings. The oceanfront swimming pool complex features lush gardens and beachside hammocks, and sweeping views of the Atlantic Ocean and the Condado resort district. La Islita is a beachside peninsula used for special evening events and dinners amidst warm ocean breezes.

El San Juan Resort & Casino

The property: The El San Juan’s beachfront location is perhaps the best among the company’s properties in Puerto Rico’s capital city and is another property with links to the city’s golden era of the 1950’s and 1960’s, when it emerged as a popular vacation destination for entertainers like Frank Sinatra, Sammy Davis, Jr. and Nat “King” Cole, all of whom performed at the 386-room hotel.

The lobby features carved mahogany walls, magnificently intricate crystal chandeliers, four sophisticated bars and the Club Brava and Ultra Lounge, a velvet-rope nightclub. The resort also features a Meat Market Miami steakhouse outlet among its 10 dining options. Live music events held each evening in the hotel’s trendy lobby attract locals and hotel guests alike.

What makes it special: The resort’s Encanto Beach Club offers 24 canopied daybeds and three private cabanas featuring high-definition televisions, stocked mini-refrigerators and power outlets (for charging smart phones and other devices). There are also 25 retro-circular lounging pods, hammocks, swings and a swim-up bar.

El Conquistador Resort, a Waldorf Astoria Resort

The property: The sprawling 500-acre luxury resort, located about one hour outside of San Juan in the city of Fajardo, is dramatically located atop a 300-foot bluff on the island’s eastern edge. The stately property features guest rooms and suites divided into five villages, including Las Casitas Village, a boutique resort-within-a-resort featuring one-, two- and three-bedroom villas that offer 24-hour butler service.

The property is best described in superlatives, which range from the unparalleled views offered from the infinity Jacuzzi overlooking the converging waters of the Caribbean Sea and Atlantic Ocean, to the resort’s 23 bars and restaurants, highlights by the sumptuous Chops Steakhouse. The family friendly resort also features Coqui Water Park, a waterfront aquatic playground, and a three-level Waldorf Astoria spa, and an 18-hole Arthur-Hills designed golf course.  

What makes it special: The resort features Palomino Island, its own private island featuring motorized and non-motorized water sports, snorkeling, hiking and horseback riding trails, all set among white sands surrounded by crisp blue waters.