Highland Beach pet-friendly rentals

We found 238 pet-friendly 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 pet-friendly holiday home in Highland Beach?
A range of factors can affect the price of a pet-friendly holiday home, including its size, amenities and when you prefer to travel. With Stayz, it's easy to find a perfect space in Highland Beach for you and your pup, and still save some cash. Simply apply a few filters to search by things like price per night and discounts. Order the results from lowest to highest price, then book your favourite.
When is the best time to book a pet-friendly holiday home in Highland Beach?
August is a wonderful month to get away to Highland Beach with your adventure-loving dog by your side. It's also when many people book a pet-friendly holiday home. Journey to this part of Annapolis during this time of year and you can expect temperatures of between 21ºC (21ºC) and 29ºC (29ºC).
Where can I rent a pet-friendly holiday home with great views?
It's a breeze to find a pet-friendly holiday home in Highland Beach with stunning views with our handy filter tool. Select "Location" to view properties in scenic areas or with specific outlooks that both you and your pooch will enjoy. You can also find holiday homes that previous Stayz guests rave about by clicking on "Guest rating."
Can I book a pet-friendly holiday home near the beach?
Give your dog the thrill of running, splashing and jumping along the shore at one of our pet-friendly holiday homes by the beach in Highland Beach. Look for properties near popular areas like Sandy Point Beach and Triton Beach.
Do any pet-friendly holiday homes in Highland Beach have a garden?
To find pet-friendly holiday homes in Highland Beach with an outdoor area, select "Garden or backyard" under the features and amenities filter. Some of our properties come with fenced gardens, while others are near trails, parks or other pet-friendly areas.
Can I book a pet-friendly cabin or lodge in Highland Beach?
Use our "Pet-friendly" filter tool to discover the perfect stay. Many of our pet-friendly cabins or lodges in Highland Beach have yard areas, so your pup will have room to exercise. There'll also be a place for your pet to sleep comfortably, and sometimes even a welcome pack with a few surprises in them to enjoy.
What are the top things to do in Highland Beach?
There are plenty of family-friendly sights to explore around Highland Beach, including Maryland Quiet Waters Park, Annapolis Maritime Museum and Annapolis Landing Marina. With pet-friendly holiday homes for every type of guest, including four-legged ones, Stayz is your gateway to exciting family adventures.