10 Best May Vacations

The best thing about the month of May is that the weather is nice almost anywhere in the Northern Hemisphere! With that in mind, here is a list of the 10 best May vacations you can take if your vacation plans have you taking off in spring. Vacation rentals are abundant in each one, so you'll have plenty of options to choose from.

  1. Connecticut

    Connecticut rental #594968vb

    Spring hits southern New England in a special way – unlike anywhere else in the world. The area’s harsh winters give way suddenly to a lively green season whose beauty is matched only by the area’s famously stunning autumn. A drive up Interstate 95 will take you past the big, beautiful, century-old houses owned by the well-to-do of Greenwich, up to the urban pulse of New Haven, home of Yale University and some of the best pizza on Earth.

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  2. Los Angeles

    Los Angeles rental #936677

    Los Angeles is a must-see on anyone's list. Between the world-famous beaches, art galleries and Hollywood sights, L.A. packs so many places to go and things to see that you would need all of May to even scratch the surface. Though the city's beautiful climate and celebrities steal most of the spotlight, most folks don't realize it houses one of the country's best beaches - Hermosa Beach - one of its elite music venues - Walt Disney Concert Hall - and one its best museums - the Getty Center. And for sports fans, nothing beats a gorgeous afternoon at Dodger Stadium or an evening rubbing shoulders with Jack Nicholson at a Lakers playoff game at the Staples Center.

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  3. Boston

    Boston rental #3543585

    One of the very first truly great American cities and the “cradle of American liberty,” Boston is incredibly rich in history. Like much of New England, spring is one of the best times of year to visit. After a day full of American history, you can spend the evening in a living monument to baseball history by taking a tour or watching a Red Sox game in Fenway Park. While you're in town, be sure to enjoy some lobster from just up the coast in Maine as well as some of Boston's famous clam chowder.

    While you're in town, be sure to soak in the seasonal blooms at the Arnold Arboretum or view wildlife at the Audubon Society, which stretches over more than 34,000 acres of conservation land.

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  4. Miami

    Miami rental #3009430

    No list of the 10 best May vacations would be complete without a Florida metropolis. Miami is simply the biggest, most diverse, most exciting city in the American Southeast. The beaches are beautiful, the population is gorgeous and the nightlife is hopping.

    You can enjoy the sun-soaked pleasures of South Beach, return to the 1920s with the Art Deco architecture on Ocean Drive or flock to home design stores in the Design District. If Cuban food and coffee are your kryptonite, head to Little Havana. In Miami, the beaches are beautiful - check out Crandon Park Beach for the parties and Matheson Hammock Park Beach for the families.

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  5. London

    London rental #1383750

    London's cold winters absolutely erupt into an explosion of green and color in spring. Hyde Park buzzes with people as everyone wants to be outside. The weather is perfect for walking neighborhoods like Notting Hill , taking a boat ride on the Thames, or visiting the iconic landmarks of one of the world's most historical cities.

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  6. Hollywood

    Hollywood rental #3847957

    If you’re a film buff, Hollywood is a must. You’ll want to check out the Walk of Fame on Hollywood Boulevard or stop by Mann's Chinese Theater. If you’re in town long enough, take in a concert at the Hollywood Bowl, a legendary amphitheater. When travelers list their favorite places to visit, Hollywood is always one of the 10 best. May vacations always be this easy to plan!

    View more Hollywood, California vacation rentals here >>>

  7. Chicago

    Chicago rental #974965

    Continuing the theme of getaways that beat early summer heat, there is Chicago. Though during winter Chicago is one of the coldest places in the continental US, in springtime it's one of the coolest. Walk along Lake Michigan, or visit the Sears Tower, the tallest building in the United States. Don't leave town without having an Italian beef sandwich and some of Chicago's famous pizza.

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  8. San Francisco

    San Francisco rental #3477430

    If the idea of going somewhere cool in May appeals to you, you should consider San Francisco. Mark Twain supposedly once said, “The coldest winter I ever spent was a summer in San Francisco.” That means the weather in May is just right. Get some great dim sum in Chinatown, walk around Fisherman's Wharf, or take a tour of Alcatraz.

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  9. Tampa, Florida

    Tampa, Florida rental #3165475

    The Tampa Bay area includes Clearwater and St. Petersburg, and it’s a great place for a baseball fan—in the early spring, before the season starts, the Yankees train there, and by May you can catch a Tampa Bay Rays' home game. Swing by the Straz Center for a live performance, or bring the kids to the Big Cat Rescue to stare into the eyes of lions and cheetahs.

    View more Tampa, Florida vacation rentals here >>>

  10. New York City

    New York City rental #647968


    The lyrics to the old jazz standard “How About You” say, “I like New York in June…,” but May is wonderful. Summertime weather in New York City can be humid, but in May the weather is perfect. It just begs you to stroll through Central Park. Since many kids are still in school in May, New York's renowned museums are less crowded. If you're a sports fan, be sure to visit Yankee Stadium or Madison Square Garden – or both.

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Connecticut Rentals Near the Ocean

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3 - 180  Night Minimum Stay
1 BR, 1 BA, Sleeps 4


2 - 7  Night Minimum Stay
6 BR, 2 BA, 2 HF, Sleeps 13


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3  Night Minimum Stay
4 BR, 2 BA, Sleeps 8


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1  Night Minimum Stay
3 BR, 2 BA, Sleeps 10