
Beachfront holiday rental in Highland Beach
Find and book unique beachfront homes on Airbnb
Top-rated beachfront accommodation in Highland Beach
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Highland Beach beachfront rentals
Pet-friendly beachfront home rentals

The Shore House

A Little Piece of Paradise - Waterfront Home

Wonderful Cottage Nestled On Chesapeake Bay

Little Slice of Cambridge. Newly listed, 2 bedroom

Cozy 3-bedroom cottage steps away from the water.

Farmhouse by the bay! Beach and pier access.

Waterfront Getaway - Dock UR Boat & Walk to Beach

Magical Bayfrnt Home, Pier, Beach, Fossils, trails
Beachfront home rentals with a pool

Chestertown Watson Family Farm

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

10 Minutes to St. Michaels with a Private Pool

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

Clearview | an ESVR property

Hidden Gem In Heart of Cambridge
Private beachfront home rentals

Private Cottage on gated estate

Nice Guest Suite at Chesapeake Bay

Waterfront w/ Private Pier, 35 Mins to Annapolis

Waterfront South River Edgewater Sunrises & Beach!

Mac's Waterfront Wonder

*Waterfront Sunset Bayview* sleeps 6

Quiet Getaway in Waterfront Community

Country House on the Bay
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- Nationals Park
- The White House
- Lincoln Park
- National Mall
- Hampden
- National Museum of African American History and Culture
- Georgetown University
- Sandy Point State Park
- Smithsonian American Art Museum
- Smithsonian National Museum of Natural History
- Arlington National Cemetery
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Washington Monument
- National Harbor
- Great Falls Park
- Oriole Park at Camden Yards
- District Wharf
- Heritage Shores
- Six Flags America
- American African Museum
- Meridian Hill Park
- Congressional Country Club