
Beachfront vacation rentals in Highland Beach
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Highland Beach
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
Vacation 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

Ferry Bridge House

The Shore House

A Little Piece of Paradise - Waterfront Home

Wonderful Cottage Nestled On Chesapeake Bay

Waterfront Getaway - Dock UR Boat & Walk to Beach

Panoramic water views

Cozy Waterfront Cottage - Pet Friendly

Bay Home in Annapolis with Private Dock
Beachfront home rentals with a pool

Chestertown Watson Family Farm

Charming RV With A Water View

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

10 Minutes to St. Michaels with a Private Pool
Private beachfront home rentals

Waterfront South River Edgewater Sunrises & Beach!

*Waterfront Sunset Bayview* sleeps 6

Quiet Getaway in Waterfront Community

Cape St Claire waterfront getaway "The Apartment"

Country House on the Bay

Quaint Waterfront- access, Private Shorehouse-unit

• Peaceful Point • A relaxing waterfront retreat

Chesapeake Bay Escape | Cozy Couples Retreat
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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
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- District Wharf
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- American African Museum
- Meridian Hill Park
- Congressional Country Club
- Family travel hub Tips and inspiration
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