As springtime flowers begin to bloom in May, cities across the U.S. are bustling with activity and boasting mild temperatures perfect for a vacation. Set your sights on destinations like the sunny beaches of Miami Beach and San Diego, where art festivals and beachfront brew fests are abundant. Spend your late spring days relaxing in your United States vacation rental, which range from coastal cottages with breathtaking views to cozy houses in quiet neighborhoods. When planning your next May vacation, consider these U.S. getaways.

1. Miami Beach, Florida

Miami Beach offers fun in the sun and an art culture rich with museums, theaters, and galleries. May is the peak time to travel to this vacation destination, primarily, because you can avoid the crowds when venturing out to South Beach or relaxing on one of the sandy beaches. When vacationing in May, you can take advantage of the city’s Taste of the Nation at Soho Studios that brings together chefs and mixologists for a weekend festival designed to satisfy your hunger. Mid-May in Miami Beach also brings the Taste of Haiti in the city, which includes live music and authentic food.

Find vacation rentals near Miami Beach

2. Washington, D.C.

A vacation rental in Washington, D.C. puts you in the heart of the capital, but it also gives you the opportunity to enjoy the city’s May festivals, such as the DC Funk Parade, the Shenandoah Apple Blossom Festival, and the seasonal opening of the National Cathedral Flower Mart. Spend your time touring the Newseum, taking pictures outside the White House, and catching up on your history in this historic city. When visiting in early May, you get the chance to participate in the Around the World Embassy Tour, which showcases performers, lecturers, artists, and teachers from the Middle East, Asia, and Africa.

Find vacation rentals near Washington, D.C.

3. San Diego, California

Sun seekers often retreat to San Diego during May to relish in the 70 miles of coastline the city has to offer. A visit in May, though, also puts you in the heart of San Diego’s thriving Cinco de Mayo celebration that includes live music and brews at the San Diego Brewers Guild’s Rhythm and Brews Festival and the San Diego Ho’olaule’a Hawaiian Cultural Festival with crafts, food, and workshops. Shop the week away at the floral wonderland held in the Flower Hill Promenade throughout the month or join in the festivities at the Asian Cultural Festival.

Find vacation rentals near San Diego

4. Las Vegas, Nevada

The city that never sleeps provides plenty of opportunities to see live acts, gamble at the casinos, and wander through the Strip. America’s entertainment mecca is home to the Billboard Music Awards in May, as well as the Vegas Uncork’d festival that brings together renowned chefs from the elite hotels in the city for savory food you won’t want to miss.

Find vacation rentals near Las Vegas

Find the perfect United States vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

5. New York City, New York

Dodge the crowds and the summer heat when vacationing in the Big Apple in May. Stroll through Central Park, take a ferry ride to see the Statue of Liberty, and take in a Broadway show. In May, the city hosts the Ninth Avenue International Food Festival as well as the Dance Parade, where performers take over the streets. Bike through the streets of New York when participating in the Great 5 Borough Bike Tour or expand your film repertoire at the Tribeca Film Festival.

Find vacation rentals near New York City

6. Los Angeles, California

Surround yourself with accomplished and aspiring actors when opting for a vacation rental in Los Angeles. With beaches lining the coast, your family can enjoy a relaxing beach stay or take part in the popular May events the city has to offer, such as the LA Vegan Beer Fest, The Original Renaissance Pleasure Faire, and the Santa Monica Festival. Make this vacation destination even more exciting with a trip to the Hollywood Walk of Fame.

Find vacation rentals near Los Angeles

7. Philadelphia, Pennsylvania

Philadelphia is home to several festivals during the month of May, when the temperatures are just right for some outdoor fun. After a relaxing morning in your vacation rental, head over to the Spruce Street Harbor Park for the opening of the city’s waterfront park. Roller skate during the day at the Blue Cross RiverRink Summerfest or see the sky light up in the evenings at the Philadelphia Chinese Lantern Festival in May. Spend some time during your May vacation visiting the popular attractions in Philadelphia, such as Franklin Square, the Liberty Bell, and the Betsy Ross House.

Find vacation rentals near Philadelphia

8. Cape Cod, Massachusetts

Arrive in Cape Cod during the peak season and stay in a seaside vacation rental that offers breathtaking views. Visiting Cape Cod in May allows you to take advantage of less crowds when heading to the beach, as well as shorter lines at the city’s attractions, such as the New England Fire and History Museum and the Cape Cod Potato Chip Company’s factory. Enjoy the Cape Cod Maritime Days celebration that includes an art gallery and lighthouse tours, or plan your vacation around Memorial Day to join in the fun of the Figawi Regatta.

Find vacation rentals near Cape Cod

9. Louisville, Kentucky

Horse race fans flock to Louisville during the month of May for the Kentucky Derby, an annual event that begins with the U.S. Triple Crown of Thoroughbred Racing at Churchill Downs. Once you place your bets and enjoy the races, head over to the Kentucky Reggae Festival for some live music and food. The Mayor’s Hike, Bike, and Paddle is also a popular May event in Louisville, allowing you and the family to enjoy the spring weather of the Midwest while getting some exercise before retreating to your cozy vacation rental.

Find vacation rentals near Louisville

10. Charleston, South Carolina

Charleston is full of charm with access to beachfront vacation rentals and access to the big city. See the Southern mansions surrounding Battery Park or get in some retail therapy on King Street. The historical city also hosts The Taste of Gullah in May where you can sample Southern favorites and the five-day North Charleston Art Fest that puts you in touch with live musical performances, pieces of artwork from local and national artists, and dance acts.

Find vacation rentals near Charleston

11. St. Louis, Missouri

The Gateway City, home to the Arch, offers mild temperatures in May in addition to local events and festivals that appeal to all ages. Taste brews from 80 breweries during the Annual St. Louis Microfest Beer Festival the first weekend of May before taking in a theater performance at the Muny in Forest Park. Cherokee Street hosts its annual Cinco de Mayo celebration with Mexican food provided by restaurants and street vendors. Get your fill of art and culture at the Art Fair at Laumeier during the month of May, too.

Find vacation rentals near St. Louis


Ready to go? Check out these amazing United States vacation rentals on Tripping.com.