Hollywood holiday rentals

We found 137 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Hollywood to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent 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, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting historical 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 holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Hollywood

Are you searching for things to do in the area? Venture out of your holiday home and check out everything that makes Hollywood a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Hollywood. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport options to and around Hollywood

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Hollywood?
The most sought-after types of holiday homes in Hollywood are houses. Want something different? Stayz has a variety of options to match the unique needs of our guests, so you’ll see holiday 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 holiday home in Hollywood?
The average price for a holiday home 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 cosy 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 Stayz. 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 holiday homes in Hollywood?
You’re in luck! There are. You’ll have your pick of two holiday homes that cater to pets in Hollywood. Plenty of our pet-friendly holiday homes 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 Stayz.
What are popular home amenities in Hollywood?
Some of the most popular home amenities people are searching for in Hollywood are a firepit, a garden and a barbecue grill. Whether you’re travelling with friends, family or even pets, Stayz holiday properties include the best amenities for chilling out with the people you love.
Are there holiday homes in Hollywood that welcome kids?
Bring the whole group together for a fun-packed adventure in Hollywood at one of our two family-friendly holiday 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 favourite.
What are the top attractions for families in Hollywood?
Keeping the kiddos entertained during your holiday 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 holiday homes in Hollywood?
Yes, you can take your pick from two one-bedroom homes in Hollywood. Whether you want a townhouse or an upmarket condo, Stayz’s one-bedroom homes 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 holiday homes with air conditioning in Hollywood?
Decide on your travel dates and then use our filters to view holiday homes with ac in Hollywood on Stayz. 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 holiday home in Hollywood?
The minimum age can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Hollywood you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home 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 Stayz. 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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