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Why we love it: A family-run hotel with eye-catching design and sustainable architecture

The Highlights:
- Rustic wooden cabanas surrounded by water
- Private plunge pools in each room
- Tasty local food, including breakfast, snacks, and dinner upon request

The Review:
Holbox is becoming more and more popular, thanks to its chill vibe, powdery beaches, and relative privacy compared to Tulum. Among the island’s best places to stay is this family-run retreat, just a few blocks from the shore. Here, the unique geometric design features 12 whitewashed, thatch-roofed cabanas surrounding a flooded central deck-cum-pool. Each room opens directly onto a private plunge pool that connects to the main one, creating the feeling of an overwater bungalow.

Guest room interiors are carved from sustainable cedar wood, lending a rustic air that melds perfectly with Holbox’s laid-back, eco-conscious atmosphere. There’s not much in the way of furniture beyond a few shelves and a bed clad in organic sheets, but that helps keep the focus on the fragrant cedar. Daily breakfast is included as are afternoon snacks. With advance notice, the chef will also cook you an authentic Mexican dinner using local ingredients. If you’re in need of a tipple, a tower adjacent to the lobby area has a bar with well-made cocktails and stunning ocean views. Just don’t expect fast Wi-Fi or much in the way of amenities—here, it’s all about island time.

This Scottsdale megaresort opened in 1988 as an Americanized vision of European style, which explains the white marble in the lobby, the mother-of-pearl tiles lining one of the pools, and the 11 Steinway pianos (including one in each of the four presidential suites). Over the years, though, the Phoenician has melded with its surroundings to become one of the classic Arizona desert hotel experiences. The 27-hole golf course, the 11 tennis courts, the eight pools (one with a 165-foot waterslide), the spa, the hiking, and the alfresco dining all make it the kind of place people contemplate when they find themselves looking at a closet full of winter coats and scarves. The rooms are spacious, with large Italian marble bathrooms, and have a private terrace or balcony. The service is tip-top, and the kids’ club even features a Bunny Hoppy Hour. Recent renovations updated the hotel’s public spaces, including the lobby, restaurants, pool area, and spa.

Once the vacation home of the Italian Duchess Rosa de Ferrari, this exceptional estate was converted into a hotel in 2005. 2014 marked the arrival of a new owner and a new era for the property. Today, Hotel Esencia is an elegant small resort on one of the prettiest beaches on the Mayan Riviera. Surrounded by 50 acres of lush jungle and manicured, palm-fringed grounds, Esencia pairs the amenties and comforts of a larger hotel with the attentive care typical of a boutique property or B&B. Amenities include two swimming pools, a spa, and two restaurants. In the spacious rooms, lots of details stand out: iPod surround systems, well-stocked minifridges, 600-thread-count sheets, and walk-in closets.

For a truly relaxing vacation, the beachfront Westin Dawn Beach Resort & Spa, St. Maarten features everything you need right onsite: gamble in the casino, swim in the infinity-edge swimming pool, have a drink in the pool bar, dine at one of the three onsite restaurants, indulge with a treatment from their spa, or just enjoy the ocean views from your room. Friendly staff ensure a personalized stay, enhancing the overall experience. The Westin St. Maarten is also an excellent choice for families, as their Westin Kids Club® offers games, activities, crafts, and day trips. Babysitting services are also available. And for those trying to stay healthy while on vacation, the Westin Essence program offers SuperFoodsRx™ meals, a fitness studio, spa, and Westin Heavenly® Beds to help you be kind to your body. Free Wi-Fi is available throughout the property. Maarten.

One of the top spots to watch the sun set behind the islands that make up the Bacuit Archipelago, Cadlao Resort is also one of El Nido’s most enticing resorts. Most of the 25 rooms offer views of El Nido Bay or the South China Sea--but, for those sunsets, consider taking them in while taking a dip in the inifinity pool. Decor is spare but elegant, with pops of color all around. If you find yourself antsy to get off property, there’s no better spot than the resort’s private beach, a 45-minute boat ride away. After? Perhaps a spa appointment before dinner at the on-site restaurant, where the catch of the day arrives wrapped in a banana leaf.

The W Santiago is where the cool kids stay. Which other hotel would dare to have a sign reading “WHATEVER” at the entrance? Since opening in 2009, the hotel has earned a strong following, both from locals and visitors. Dimly lit with a color scheme of purples, greens, and black, the rooms are modern, with full-length windows overlooking the city. Located in Santiago’s financial district, officially known as El Golf, the W is part of a large skyscraper (hotel reception is on the fourth floor) filled with restaurants and shops. The 196 rooms reach to the 21st floor, and the W has arguably the best roof terrace in town (Hotel Noi Vitacura being a close contender). The roof terrace has an infinity pool, knockout city views, and a heli-pad for those who want to whiz off to wine country or hit the ski slopes in speedy style.

With more than 400 shipwrecks and its fair share of coral reefs, St. Kitts is a favorite of the scuba set. To try your hand at the hobby, consider staying at Bird Rock Beach Hotel, which houses one of the island’s most popular dive operators. Here, guests can charter a boat to nearby Devil’s Cave and swim among barracuda, lobsters, and nurse sharks, then retire to one of 46 tropical-hued rooms overlooking the sea. Less adventurous travelers can visit the on-site dolphin park, sunbathe on the private beach, or simply sip rum punches from the pool’s swim-up bar. Hotel staff is also happy to arrange off-site activities like catamaran cruises, rainforest treks, and volcano crater tours.

Sunny as it is, Cabo has never been known for its beaches because of its rough surf. Not so at adults-only ME, however, which sits on the area’s only swimmable stretch of shoreline, in view of the famous El Arco rock formation. While the 162 rooms are the picture of tranquility (deep soaking tubs, private balconies), the hotel itself boasts a party atmosphere—a house DJ spins by the pool, and bottle service is available in the cabanas on the pool terrace. Thankfully, there’s also a spa specializing in traditional Aztec and Mayan-inspired treatments (don’t miss the temazcal cleansing ritual), so you can rejuvenate before returning home.

Atop towering Cerro San Cristóbal, there are two municipal pools where many families go to cool off during the summer: Tupahue and Antilén. Conveniently, these all have fabulous views of the city below. However, they do come with a price tag of US$12 for the lower-elevation Tupahue, and US$15 for Antilén, which keeps crowds to manageable levels in January and February.

An ivy-covered, 17th-century mansion near the beautiful Place de Vosges is now the site of an intimate, five-star hotel. A favorite of sophisticated travelers who value privacy over hype, Le Pavillon de la Reine (named “Reine” in homage of a stay by Queen Anne of Austria) features striking interiors that blend original architectural details and aristocratic portraits with bright colors and contemporary furnishings. The 56 rooms and suites are similarly posh, with touches like patterned wallpaper and textiles, antique chandeliers, marble mantles, and flower-filled window boxes, plus luxe Codge bath products.

Perched on a steep hill in the lovely neighborhood of Alfama, you will in no doubt leave with a great souvenir or gift. Sellers throw down blankets or rugs in rows and sell a variety of hand-made goods, antiques, books, clothes, military objects, etc. I took home two wonderful brass bottle openers and a couple of old world maps. Getting to the market is easy and the trip there is quite beautiful; take the Tram 28, or Tram 12 up the hill through the tight, and narrow neighborhood streets (becos). After you’ve spent all of your Euro, take a short walk over to the Santa Engracia Church, Museum of Decorative Arts, or the National Pantheon. Oh, and don’t forget to take in the views and snap a few pictures.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.

Reach Falls is an off-the-beaten-path delight. Located up in the John Crow Mountains on Jamaica’s east coast, this 30-foot jade-colored cascade tumbles into several pools in the surrounding rain forest. You’ll need a bathing suit and a waterproof camera to capture the natural splendor. Local guides are available to help you make your way across the swimming holes and levels, and show you the best spots. Or you can explore it solo. Because of its distance from tourism spots, there are no crowds, no harassment, just an entrance fee to your very own Garden of Eden. On-site changing rooms are available as you exit by the parking lot. Small fun fact: The falls play a minor role in the 1988 Tom Cruise movie Cocktail.

Why we love it: A stylish stay that brings Miami glam to Clearwater Beach

The Highlights:
- Ocean views from nearly every guest room
- A stunning, zero-entry pool overlooking the beach
- A gorgeous art collection with original pieces by Christopher Still

The Review:
A sleek high-rise overlooking Clearwater Beach, Opal Sands Resort stands out for its modern architecture and stylish vibe. Here, everything from the guest rooms to the restaurants to the events venues feature sweeping views of the Gulf of Mexico, putting guests squarely in a beach frame of mind. The 230 rooms and suites feature generously sized layouts, complete with deluxe bedding, spa-style bathrooms, and private balconies framing Clearwater’s famous sunsets, while common spaces come decorated with an impressive art collection both created and curated by Floridian master Christopher Still.

When not taking in the vistas, guests can sunbathe by the zero-entry pool and hot tub, or rent a beach chair or cabana and head down to Clearwater Beach. Also available are a waterfront fitness center, a full-service spa, complimentary bicycle rentals, and a corn hole toss on the event lawn. There are even four dining outlets on site, from Sea-Guini (for freshly caught seafood and handmade pastas) to the Sandbar (for cocktails and live music right on the beach).

The centerpiece of a vast resort, golf club, and residential community complex, Rosewood Bermuda sits on 240 acres of waterfront land overlooking Castle Harbour, Harrington Sound, and the Atlantic Ocean. The recently refurbished resort is anchored by the Manor House, where 88 guest rooms blend classic cottage-style architecture and modern interiors that continue to set the standard for today’s luxury seekers: think canopy and four-poster beds, plantation shutters, and colonial-era antiques, all set against a cool white backdrop. Spring for a deluxe poolside room, which also has access to a private poolside daybed. Just don’t expect too much down time. Three on-site restaurants and two bars are beyond selfie-worthy, treatments at the spa incorporate local ingredients like cedar and juniper, and hotel guests receive membership to the 18-hole Roger Rulewich–designed golf course, tennis courts, and a beach club that sits on an exclusive stretch of pink sand for the duration of their stay.