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Highland Beach, Annapolis, Maryland, United States of America

Highland Beach holiday rentals

We found 341 holiday rentals — enter your dates for availability

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Find spaces that suit your style

Houses

View 265 Houses

Condos/Apartments

View 58 Condos/Apartments

Townhouses

View 27 Townhouses

Studios

View 37 Studios

Find the best place to stay — Highland Beach

Annapolis - Bayfront Community, 4 Bedrooms (2 Kings) - Convenient & Private

Sleeps 8 · 4 Bedrooms · 2 Bathrooms
AU$ 882 avg/night
(1)

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Sleeps 11 · 4 Bedrooms · 4 Bathrooms
AU$ 656 avg/night
(42)

Kindred Moss Cottage: Cozy Beach Cottage: Newly Remodeled and Family Friendly!

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 506 avg/night
(33)

Annapolis waterfront "tiny house" in garden setting

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 242 avg/night
(94)

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

Sleeps 4 · 2 Bedrooms · 1 Bathroom
AU$ 267 avg/night
(74)

The Cottage on Spa Creek

Sleeps 4 · 2 Bedrooms · 1 Bathroom
AU$ 316 avg/night
(24)

Search 341 holiday rentals

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How many holiday accommodation are available around Highland Beach?

Our 2021 accommodation listings offer a large selection of 341 holiday rentals around Highland Beach. From 265 holiday houses to 58 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Highland Beach is on Stayz.

Can I rent Houses in Highland Beach?

Yes, of course. Stayz offers 265 Houses in Highland Beach. Our other popular types of Highland Beach holiday rentals include:

  • Condos/Apartments: 58 holiday houses
  • Townhouses: 27 holiday houses
  • Cottages: 13 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool in Highland Beach?

Yes, you can select your preferred holiday accommodation with pool among our 62 holiday homes with pool available in Highland Beach. Please use our search bar to access the selection of holiday rentals available.