Highland Beach beach rentals

We found 107 beach rentals — enter your dates for availability

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

Frequently asked questions

How much does it cost to stay in a beach holiday rental in Highland Beach?
Scoring savings on your beach holiday rental in Highland Beach is a cinch with our filter tool. Search by location, price, amenities and any other personal preferences to find a getaway that matches your needs and budget. Small or large, rustic or regal, cottage or chalet — we've got properties for all kinds of seaside escapes.
When is the best time to book a beach holiday rental in Highland Beach?
While there are loads of amazing times to visit Highland Beach, most Stayz guests book their beach holiday rental in August. Travel to this corner of Annapolis then and you can expect average temperatures of between 21ºC and 29ºC. If there are certain things on your must-do list, make sure you check that they're available first before booking your getaway.
Where can I book a Highland Beach beach holiday rental with great views?
Stayz makes it simple to find the striking views you're looking for in your holiday house. Just use the "Location" filter to narrow down the type of area you prefer to be in, and the views you want to gaze out at, while searching for your beach holiday rental in Highland Beach.
What are the most popular beaches in Highland Beach?
When it comes to the most popular beaches in Highland Beach, Sandy Point Beach should be at the top of your list. Then, slip away to Triton Beach and end your day with a relaxing sunset stroll.
What are the top things to do in Highland Beach?
Keep all the crew entertained by checking out Maryland Quiet Waters Park, Annapolis Maritime Museum and Annapolis Landing Marina. These are just a few of the family-friendly sights you'll find around Highland Beach. Whatever your idea of the perfect seaside getaway, our beach holiday rentals have the space you need to connect.
Why should I book my beach holiday rental with Stayz?
At Stayz, we recognise the importance of a stress-free retreat, which is why we have our Book with Confidence Guarantee. That means when you book a beach holiday rental, you'll have access to our 24/7 customer support team should any unforeseen circumstances arise. Not to mention most of our stays also come with flexible cancellation policies.