Hollywood vacation rentals

We found 138 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Hollywood to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting historic Hollywood

Enjoy the history and other features of Hollywood. Renowned for its restaurants, sporting events and shopping, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Hollywood

Do you want to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Hollywood has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Perigeaux Vineyards and Winery (5.4 mi / 8.8 km)
  • Port of Leonardtown Winery (6 mi / 9.6 km)
  • Running Hare Vineyard (10.8 mi / 17.4 km)
  • Maryland International Raceway (14.4 mi / 23.1 km)
  • Breton Bay Golf Course (8.1 mi / 13 km)
  • Wicomico Shores Golf Course (15.2 mi / 24.4 km)

Exploring the natural landscape of Hollywood

Whether you're an active traveler or just want to take in the scenery, Hollywood is a great place to get outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Annmarie Sculpture Garden and Arts Center (6.5 mi / 10.4 km)
  • St. Mary's River State Park (6.8 mi / 11 km)
  • Drum Point Lake (8.5 mi / 13.6 km)
  • Flag Ponds Nature Park (8.7 mi / 13.9 km)
  • Seahorse Beach (8.9 mi / 14.3 km)
  • Battle Creek Cypress Swamp Sanctuary (9.2 mi / 14.8 km)

Transportation options to and around Hollywood

Fly into Ronald Reagan Washington National Airport (DCA), the closest airport, located 42.3 mi (68.1 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hollywood?
The most sought-after types of vacation rentals in Hollywood are houses. Want something different? Vrbo has a variety of options to match the unique needs of our guests, so you’ll see vacation homes in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Hollywood?
The average price for a vacation rental in Hollywood is based on a number of factors, like property type, season and length of stay. Whether you’re searching for a sprawling villa with a pool or a cozy cabin just enough for two, just add your dates of travel to find stays with fantastic value.
How much does it cost to rent a beach house in Hollywood?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Put in your Hollywood travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the features and amenities you want in your beach house.
Are there pet-friendly vacation rentals in Hollywood?
You’re in luck! There are. You’ll have your pick of two vacation rentals that cater to pets in Hollywood. Plenty of our pet-friendly vacation rentals come with a backyard for your four-legged fur baby to run around in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find your place on Vrbo.
What are popular rental amenities in Hollywood?
Some of the most popular rental amenities people are searching for in Hollywood are a firepit, a garden and a barbecue grill. Whether you’re traveling with friends, family or even pets, Vrbo vacation properties include the best amenities for chilling out with the people you love.
Are there vacation rentals in Hollywood that welcome kids?
Bring the whole group together for a fun-packed adventure in Hollywood at one of our two family-friendly vacation properties. Many of these stays come with conveniences that are suitable for getaways with the little ones, such as full kitchens, living rooms and entertainment units. Simply check the “Properties good for families” filter box and choose your favorite.
What are the top attractions for families in Hollywood?
Keeping the kiddos entertained during your vacation in Hollywood is child’s play with these leading family-friendly attractions:

  • Patuxent River Naval Air Museum
  • St. Marys River State Park
  • Drum Point Lighthouse

Are there one-bedroom vacation rentals in Hollywood?
Yes, you can take your pick from two one-bedroom rentals in Hollywood. Whether you want a townhouse or an upmarket condo, Vrbo’s one-bedroom rentals are great if you don’t need lots of space. One of the best parts about having your own pad? You won’t have to share your getaway with strangers.
How can I find vacation rentals with air conditioning in Hollywood?
Decide on your travel dates and then use our filters to view vacation rentals with ac in Hollywood on Vrbo. With two air-conditioned properties to choose from here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Hollywood?
The minimum age can vary across properties on Vrbo, so be sure to look at the rules of the vacation rental in Hollywood you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Hollywood for?
It really depends on the Hollywood property. To see a list of options offering extended stays, simply type your dates and number of guests into Vrbo. You can enjoy having the property to yourself, along with the comforts of home like a fully-equipped kitchen and a yard to run around in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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