Saint-Barthélemy (St. Barts/St. Barths)
Most affordable time to travel: November. The average weekly rate for two-bedroom properties during this time is around $4,312.
Peak time to travel: Mid- to late December. The average weekly rate for two-bedroom properties during the peak season is around $12,900.
Vibe: St. Barts is home to 14 stunning beaches, most of which remain crowd-free even during the peak season. A popular destination for celebrities, St. Barts has a variety of designer boutiques, an array of fine dining restaurants, yacht and jet ski rentals, and a breathtaking scenery of mountains, green hills, and glistening bays.
Kapolei, Hawaii
Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $2,626.
Peak time to travel: End of December. The average weekly rate for two-bedroom properties during this time is around $3,850.
Vibe: Kapolei, known as Oahu's "second city" after Honolulu, is built on former sugarcane and pineapple plantations. It has a sunny climate, lush green golf courses (including the Kapolei Golf Course and Ko Olina Golf Club), diverse dining options, and lots of water activities.
St. Martin
Most affordable time to travel: Early August. The average weekly rate for two-bedroom properties during this time is around $2,272.
Peak time to travel: Most of December. The average weekly rate for two-bedroom properties during the peak season is around $5,600.
Vibe: The island of St. Martin is split into two sides: the Dutch half of Sint Maarten, which is filled with bustling nightlife, shopping centers, sprawling resorts, and gleaming beaches; and the French half of St. Martin, which has a quieter ambience, with white-sand beaches, small town squares, and charming mountainside scenery.
The island has 37 beaches in total and offers visitors a wide range of water activities, including everything from scuba diving and snorkeling to yachting and windsurfing.
St. John, US Virgin Islands
Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $2,670.
Peak time to travel: Late December. The average weekly rate for two-bedroom properties during the peak season is around $5,600.
Vibe: With two-thirds of its land area comprising a pristine natural park, St. John is a prime destination for those looking to escape the hustle and bustle of their hometowns.
The smallest of the US Virgin Islands, St. John is home to many unspoiled beaches, like the popular Trunk Bay and Cinnamon Bay, where travelers can engage in snorkeling, windsurfing, and kayaking.
Accommodations include everything from upscale resorts to intimate eco-tents.
London, England
Most affordable time to travel: Early July. The average weekly rate for two-bedroom properties during this time is around $1,986.
Peak time to travel: Mid-July. The average weekly rate for two-bedroom properties during the peak season is around $3,551.
Vibe: There's lots to explore in England's capital, from the Tate Modern and Victoria and Albert Museum to the vast parks and open spaces that comprise one-third of the city.
There are more than 6,000 restaurants, bustling outdoor markets, and several beautiful escapes, like Kew Gardens or the Hampton Court Palace, which offers stunning panoramas of London’s riverside.
Beaver Creek, Colorado
Most affordable time to travel: Mid-November. The average weekly rate for two-bedroom properties during this time is around $2,100.
Peak time to travel: Mid-December to February. The average weekly rate for two-bedroom properties during the peak season is around $4,000.
Vibe: Athletes and spectators flock here for the famed ski event, the Birds of Prey Men’s World Cup. Beaver Creek is home to three distinct mountain areas that offer skiers trails of all levels.
Besides its snowy terrain, Beaver Creek also has expansive trail systems, chairlift rides, and a variety of shops, restaurants, and spas to visit year-round.
Santorini, Greece
Most affordable time to travel: Mid-February. The average weekly rate for two-bedroom properties during this time is around $727.
Peak time to travel: Late June. The average weekly rate for two-bedroom properties during the peak season is around $2,426.
Vibe: Santorini is composed of a group of islands that include Thíra, Thirassiá, Asproníssi, Palea and Nea Kaméni. Its multicolored beaches are the product of volcanic eruptions that have lined its sands with spectacular rock formations and red, black, and white pebbles.
Thíra is the island known for its cliffside Cycladic houses, but all of Santorini offers world-class wineries and restaurants, where you can sample traditional Greek food.
Providenciales, Turks and Caicos
Most affordable time to travel: Late March. The average weekly rate for two-bedroom properties during this time is around $1,662.
Peak time to travel: Mid- to late December. The average weekly rate for two-bedroom properties during the peak season is around $2,695.
Vibe: Provo, as it is often called, is home to beautiful white-sand beaches, modern resorts, top-notch spas, and a championship-caliber golf course. Get lost in the crystal-clear waters of the Chalk Sound National Park, or spend your time wandering through its numerous restaurants, shops, bars, and cafes.
Honolulu, Hawaii
Most affordable time to travel: Mid- to late May. The average weekly rate for two-bedroom properties during this time is around $2,054.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $2,695.
Vibe: In Honolulu, located on the island of Oahu, you'll find everything from historic landmarks and monuments to a vibrant arts and culture scene. With an exciting nightlife scene that includes live music, fine dining, and the underground bars of the Chinatown arts district, travelers can relax on the beach during the day and explore the town at night.
San Diego, California
Most affordable time to travel: Early November and early December. The average weekly rate for two-bedroom properties during this time is around $1,036.
Peak time to travel: Late May. The average weekly rate for two-bedroom properties during the peak season is around $4,120.
Vibe: Besides world-famous tourist attractions like its zoo and museums, San Diego has more than 100 craft breweries, stylish lounges and jazz clubs, and an array of buzzing nightclubs. Thanks to easy access to fresh fish and its proximity to Mexico, San Diego is also known for its delectable Cali-Baja cuisine.
Yosemite National Park, California
Most affordable time to travel: Early November and early December. The average weekly rate for two-bedroom properties during this time is around $1,479.
Peak time to travel: Mid-to-late-October. The average weekly rate for two-bedroom properties during the peak season is around $2,114.
Vibe: Yosemite National Park is located in California's Sierra Nevada mountain range and is known for its stunning waterfalls, deep valleys, grand meadows, and giant sequoia trees. Within the park are thousands of lakes and ponds, and there are more than 800 miles of hiking trails from which to admire the gorgeous environment.
A huge draw within the park is Half Dome, a rock formation rising more than 4,700 feet above the floor of Yosemite Valley, and El Capitan, which is the largest exposed granite monolith in the world.
Miami Beach, Florida
Most affordable time to travel: Mid-June. The average weekly rate for two-bedroom properties during this time is around $1,795.
Peak time to travel: Late March. The average weekly rate for two-bedroom properties during the peak season is around $2,456.
Vibe: Beyond its radiant sun and surfing hot spots, Miami Beach is home to the South Beach Art Deco District, a collection of more than 800 architecturally protected buildings that date back to the 1930s and 1940s. On North Beach's Ocean Terrace, you'll find oceanfront hotels and cafes, where you can enjoy a bite with crystal-clear views of the ocean.
Grand Cayman, Cayman Islands
Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $1,600.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $2,712.
Vibe: As the largest of the three Cayman Islands, Grand Cayman offers a variety of sites to explore. On its west side, Grand Cayman hosts the famous Seven Mile Beach, which is known for its exquisite beauty and stretches of gleaming sand.
Its North Sound is home to Stingray City and the Sandbar, where you can play with friendly stingrays. In George Town, wander through colorful Caribbean-style buildings and browse shops selling items made by local vendors and craftsmen.
Hamilton Island, Australia
Most affordable time to travel: Most of August to November. The average weekly rate for two-bedroom properties during this time is around $1,917.
Peak time to travel: Early August. The average weekly rate for two-bedroom properties during the peak season is around $2,839.
Vibe: Hamilton Island's charming roads are paved with walking trails that offer pristine views of the ocean and its white-sand beaches.
Its selection of high-end resorts, restaurants, and bars have made it a luxurious destination, and you can stop for a golf game at the Hamilton Island Golf Club — the only 8-hole championship course on its own island in Australia.
Santa Fe, New Mexico
Most affordable time to travel: Most of January and February. The average weekly rate for two-bedroom properties during this time is around $1,100.
Peak time to travel: Mid-October to early November. The average weekly rate for two-bedroom properties during the peak season is around $1,907.
Vibe: As the oldest state capital in the US, Santa Fe is known as much for its history and its original adobe buildings as it is for its eclectic art markets, gourmet dining, fabulous museums, and upscale spas. Located at the foot of the Sangre de Cristo mountain range, Santa Fe also has lots of hiking, mountain biking, and skiing.
Newport Beach, California
Most affordable time to travel: Most of November and December. The average weekly rate for two-bedroom properties during this time is around $1,300.
Peak time to travel: Early March. The average weekly rate for two-bedroom properties during the peak season is around $2,495.
Vibe: Newport Beach has the biggest recreational harbor on the West Coast, making it a prime destination for trying out water activities that range from sunset cruises to paddle boarding.
Newport Beach also offers a variety of wine tastings, art galleries, waterfront eateries, and festivals like its Restaurant Week, the Hyatt Regency Summer Concert Series, and the Newport Beach Film Festival.
Poipu, Hawaii
Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $1,728.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $2,184.
Vibe: Located in Kauai, Poipu's sheltered coves offer gentle waves that make its beaches ideal for those looking to learn how to surf or snorkel. With its oceanfront accommodations and the Spouting Horn, where huge spouts of water can be seen flying as high as 50 feet in the air, Poipu is the perfect stop for both those who are looking for a romantic getaway and those looking for a trip filled with adventure.
Dubai, United Arab Emirates
Most affordable time to travel: Early November and early December. The average weekly rate for two-bedroom properties during this time is around $1,507.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $2,693.
Vibe: Known for its opulence, Dubai is home to the world's tallest building, the Burj Khalifa, which rises over 2,700 feet into the air. There are hundreds of other skyscrapers, plus chic restaurants and bars that host everything from cabaret shows to karaoke. You can also explore Dubai's many souq markets, which are packed with hundreds of shops.
Wailea, Hawaii
Most affordable time to travel: May and June. The average weekly rate for two-bedroom properties during this time is around $1,750.
Peak time to travel: Late March. The average weekly rate for two-bedroom properties during the peak season is around $4,200.
Vibe: Wailea is home to five crescent-shaped beaches. Located on the island of Maui, the luxurious resort community boasts incredible golf courses, breathtaking ocean views, world-class restaurants and shops, and events like the Maui Film Festival and its Whale Week in February.
Key West, Florida
Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $1,672.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $4,200.
Vibe: Key West has at different times been the home of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett, among others. Dozens of galleries line the palm-filled streets of Key West, and attractions include Hemingway's former home, a designated literary landmark and museum.
Whether you're diving, fishing, golfing, or visiting its sidewalk cafes, open-air bars, legendary pubs, and delectable restaurants, travelers will be anything but bored here.
Saint James Parish, Barbados
Most affordable time to travel: Early December. The average weekly rate for two-bedroom properties during this time is around $1,610.
Peak time to travel: Most of January and February. The average weekly rate for two-bedroom properties during the peak season is around $3,850.
Vibe: St. James is sometimes called the "platinum coast" of Barbados thanks to its glistening beaches, range of fine-dining establishments, golf courses, and luxurious accommodations. Head to the Folkestone Marine Park and Museum for kayaking, paddle boarding, and snorkeling, or take a look through the collection of shops at the Chattel Village.
Avalon, California
Most affordable time to travel: Late October to mid-November. The average weekly rate for two-bedroom properties during this time is around $2,000.
Peak time to travel: Late June. The average weekly rate for two-bedroom properties during the peak season is around $3,728.
Vibe: Avalon is Catalina Island's most-visited city. Whether exploring the city on foot, boat, or on a golf cart, visitors will enjoy admiring Avalon's blue waters and trying out its many places to eat and drink. Plus, its year-round warm climate allows for enjoyable touring no matter what time of year you visit.
Aspen, Colorado
Most affordable time to travel: Late April and early May. The average weekly rate for two-bedroom properties during this time is around $1,170.
Peak time to travel: Late December. The average weekly rate for two-bedroom properties during the peak season is around $4,515.
Vibe: Aspen is known as a top winter destination, with four separate mountains to ski. Travelers can take advantage of its legendary après-ski scene before checking out one of its many nightlife spots, like Belly Up, a 500-person live music venue. With lodges that offer majestic views of the Maroon Bells — one of the most photographed peaks in North America — Aspen is a mountain retreat visitors won't forget.
Ka'anapali, Hawaii
Most affordable time to travel: Late October to mid-November. The average weekly rate for two-bedroom properties during this time is around $2,065.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $3,800.
Vibe: Ka'anapali is located on Maui and is loved for its crystal-clear waters and beautiful beaches. Once a sleepy fishing village, Ka'anapali is now one of Maui's most popular spots, with world-class resorts, shopping, and restaurants.
