Highland Beach holiday rentals, Annapolis: holiday houses & more

Discover a selection of holiday rentals in Highland Beach that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include parking and a fireplace. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

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Find the best place to stay - Highland Beach

Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats

Sleeps 4 · 2 bedrooms · 0+ bathrooms

Top rated rentals - Highland Beach

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Fabulous! Loved our stay!

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All the privacy of home
Enjoy full kitchens, pools, gardens and more
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More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Highland Beach getaway

Learn about the unique charm of Highland Beach with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Highland Beach

Are you looking for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that Highland Beach has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Thurgood Marshall Memorial (3.6 mi / 5.8 km)
U.S. Naval Academy Golf Club (4.5 mi / 7.3 km)
South River Golf Links (5.8 mi / 9.4 km)
Bay Hills Golf Club (8 mi / 12.9 km)
Maryland Renaissance Festival (8.1 mi / 13 km)
Eisenhower Golf Course (8.4 mi / 13.6 km)

Exploring the natural features in Highland Beach

Whether you're an active traveller or just want to spend some time taking in the scenery, Highland Beach is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Maryland Quiet Waters Park (1.9 mi / 3.1 km)
Matapeake State Park (6.4 mi / 10.3 km)
Sandy Point Beach (6.8 mi / 10.9 km)
Sandy Point State Park (7 mi / 11.3 km)
Chesapeake Bay Environmental Center (12.8 mi / 20.6 km)
Fort Smallwood Park (14.4 mi / 23.2 km)

How to get to and around Highland Beach

The nearest airport is in Fort Meade, MD (FME-Tipton), located 19.2 mi (30.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Baltimore Washington International Airport (BWI), which is 20.4 mi (32.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday rental in Highland Beach?

Different things determine how much you'll pay for a holiday rental in Highland Beach, such as the season, type of property and length of stay. Still, all Vrbo homes have one thing in common — incredible value. Just enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Highland Beach?

Prices for beach houses in Highland Beach may vary depending on the type and size of the property and time of year you're travelling. Just enter your travel dates into Vrbo and the number of guests to see your options and prices. From there you can use the filters to tailor your search by ratings, nearby activities and more.

What are the top attractions for families in Highland Beach?

Keeping the kids entertained during your stay in Highland Beach is easy with these top family-friendly attractions:

Annapolis Maritime Museum
Sandy Point Beach
Annapolis Sailing School

How old do you have to be to rent a holiday rental in Highland Beach?

The minimum age can vary across properties on Vrbo, so be sure to look at the rules of the holiday rental in Highland Beach you want. But normally, it's 16, 18 or 21.

How long can I rent a holiday rental in Highland Beach for?

The length of time you can rent a holiday rental in Highland Beach is up to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With a range of features such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to find a terrific place to call your home away from home in Highland Beach.