Most Romantic Hotels in San Juan, Puerto Rico

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What hotels made our list of the most romance-sparking properties in San Juan? An iconic luxury brand's island outpost, a historic Vanderbilt mansion, a beachfront party hotel, and quite a few Old World charmers and artsy hideaways. Take a look at our picks for the most romantic hotels in San Juan, Puerto Rico.

  1. Signs of Ritz-Carlton's famous luxury are recognizable with an elegant fountain and palm trees leading to a circular entrance with uniformed doormen. Inside, 416 rooms and suites span nine categories; note that only 45 units come with balconies. All rooms have similar neutral decor that some might find generic or even slightly outdated (the cheap stucco texturing on the walls, for example, brought the look down a notch). Furnishings include work desks, flat-screen TVs, Frette linens, goose-down pillows, and stocked minibars. Marble bathrooms have tub/shower combos, Asprey London bath products, and terrycloth bathrobes. Most guests spend their time on the sand, or at the lively outdoor pool where attentive service is a focus. In the evenings, the lobby bar is the place for small plates and pre-dinner cocktails before dressed-up guests (and some locals) make their way to the on-site restaurants BLT Steak and Il Mulino.

  2. The Condado Vanderbilt Hotel is a refined and retro hotel with a long history of hosting celebrities and dignitaries. The hotel’s 319 guest rooms are both classically attractive, with dark-wood furniture and stone-topped bathroom vanities, and high-tech, with 48-inch Samsung Full HD LED Smart TVs with airplay and mirroring capabilities. Hotel features seem endless: several stylish pools (one with a small waterfall and submerged lounge chairs, and three for adults only), an exquisite spa with the island's only private hammam, an organic restaurant that oozes old-school sophistication, and a large lobby lounge with a wine and cognac bar, a cocktail bar, and an intimate cigar lounge. 

  3. There is nothing quite like European-style El Convento in the medieval city of Old San Juan. It was a convent for 252 years, and today it's the neighborhood's principal upscale hotel, offering 58 elegant rooms and suites filled with Spanish antique treasures and modern amenities. Its history is present everywhere, from the exposed wood beams to the 350-year-old Nispero tree rising high above the romantic courtyard. A nightly wine and cheese reception takes place on the terrace, allowing guests (mostly couples) to mingle while overlooking views of San Juan Bay. The main restaurant offers al fresco fine dining in the courtyard; other features include the beautiful sun terrace and small outdoor pool. Service is a priority here, and it shows.

  4. Not for traditional types, this buzzy resort from Marriott’s Renaissance series is the shining (hotel) star of Condado Beach -- and, arguably, San Juan. The airy lobby is a chic meeting space by day, and is transformed at night with low lighting and hip music. Trendy restaurants have options like sushi and sake or tapas and sangria; the seashell-shaped Perla has a 4,000-bottle wine cellar. The 232 rooms and suites have bright, sleek decor, and many come with floor-to-ceiling views of the ocean (it's definitely worth the price to upgrade). Food and drink service is provided at the beach and at the three outdoor pools. With long lines for the front desk and slow drink service, the resort can feel short-staffed.

  5. Set one of the cleanest, largest, and quietest beaches in San Juan, the El San Juan Hotel & Casino is a 382-room hotel with a laid-back party vibe. Rooms are stylish and beachy, with white furnishings and tropical accents, plus modern amenities like iPod docks and flat-screen TVs. The property features an ornate and lively lobby with weekend salsa dancing, a sprawling freeform pool with a swim-up bar, a popular nightclub, and numerous restaurants, including excellent Asian cuisine at Yamato.

  6. A great choice for romantics, the 15-room Olive Boutique Hotel has an inviting rustic-chic ambience and an upscale, yet relaxed vibe. Rooms are modern and stylish with nice extras like daily fresh cookies and L’Occitane toiletries. All rooms have spacious outdoor terraces with beautiful Spanish tiling and luxe modern furniture, and some feature Condado Lagoon views. Dining and drinking options include an intimate steak house and a sophisticated rooftop bar and lounge with a plunge pool (at night, the pool lights up and becomes a romantic spot to take a dip while sipping a signature cocktail, and rooftop parties are held throughout the year with DJs and live entertainment). Free continental breakfast and local coffee are served each morning. 

  7. Guests are greeted by name at this historic bed-and-breakfast-like hotel with an artsy, laid-back feel and beautiful Old World Spanish decor (brick floors, wood-beam ceilings, rich rugs, sculptures, and antique knickknacks). No two rooms are the same, though they're all air-conditioned and have lots of Spanish-style charm. The property's main draws include the convenient Old San Juan location, ocean views from the wine deck, lush gardens, on-site art studios, and a small but charming pool. 

  8. The 12-room Cervantes is a contemporary upper-middle-range boutique set along one of Old San Juan's most popular boulevards, walking distance to many cafes, restaurants, and historic sights. Rooms are designed for comfort, with plush Egyptian cotton bedding, marble bathrooms, and thick terrycloth robes. Most rooms have double doors that open to balconies trimmed with decorative iron railings and views of the surrounding city. There is a modern, bright restaurant where a free continental breakfast is served. While being in the heart of Old San Juan has its perks, it also comes with constant noise. 

  9. Located on a quiet side street in Old San Juan, this charming boutique hotel might make guests feel like they've stepped back in time. Each of the eight rooms is furnished differently, but all share comfortable beds, high ceilings, antique furniture, ornate light fixtures, and direct access to a sunny courtyard. In the common areas, the decor is a mix of Old World and quirky modern (like zebra-print chairs and bright oil paintings). But while the location in Old San Juan helps make this a romantic spot, the hotel lacks a pool and a full-service staff, and it's a 10-minute drive to the beach.

  10. This small, laid-back, mid-range hotel has 22 rooms along a quiet residential street in San Juan about a mile from the Condado tourist hub and a block from the beach. Charming interiors and basic Spanish-style rooms are just starting to show some age. Some rooms have private balconies (and partial ocean views), but anyone is welcome to enjoy the rooftop deck -- a great place to BYO drinks before dinner. The first-floor restaurant serves breakfast and then re-opens again for dinner with a gourmet menu and decent wine list. For more restaurant and nightlife options, just head west along Avenida Ashford via foot or taxi. Guests also have access to the (small) pool and bar at the sister property down the block. 

  11. The Dreamcatcher is an enchanting lower-middle-range hotel located in San Juan’s Ocean Park district. The guest house’s nine rooms and four apartments are decorated with antiques and art, creating an upscale yet homey ambiance. With Buddha statues dotted around tranquil grounds, abundant hammocks, vegetarian breakfasts, and daily yoga classes, the guest house is an idyllic Bohemian retreat. Located in a gated community between two big tourist districts, the setting offers plenty of local charm without leaving guests isolated from the island’s entertainment scene.

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