
Beachfront holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for beachfront rentals in Highland Beach
Pet-friendly beachfront home rentals

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

The Shore House

A Little Piece of Paradise - Waterfront Home

The Blue Crab Beach House - Free beach passes

Little Slice of Cambridge. Newly listed, 2 bedroom

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Farmhouse by the bay! Beach and pier access.

Warm fire pit under the stars on the water
Beachfront home rentals with a pool

Chestertown Watson Family Farm

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

Turtle's Nest - Hist. Cambridge

Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba

Turn Winter Blues into Blissful Views – Book Now!

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI
Private beachfront home rentals

Nice Guest Suite at Chesapeake Bay

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Waterfront w/ Private Pier, 35 Mins to Annapolis

Waterfront South River Edgewater Sunrises & Beach!

Wonderful Cottage Nestled On Chesapeake Bay

*Waterfront Sunset Bayview* sleeps 6

Quiet Getaway in Waterfront Community

Country House on the Bay
Destinations to explore
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- Nationals Park
- Lincoln Park
- Patterson Park
- National Mall
- Hampden
- Arlington National Cemetery
- Georgetown University
- Sandy Point State Park
- M&T Bank Stadium
- National Air and Space Museum
- Columbia Country Club
- National Museum of African American History and Culture
- Washington Monument
- Great Falls Park
- American African Museum
- Idlewilde Restoration Project
- The Pentagon
- Gerry Boyle Park
- National Harbor
- Leesylvania State Park
- Georgetown Waterfront Park
- Lake Presidential Golf Club
- Cove Point Beach
- Six Flags America