
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

The Shore House

A Little Piece of Paradise - Waterfront Home

Wonderful Cottage Nestled On Chesapeake Bay

Cozy 3-bedroom cottage steps away from the water.

Waterfront Getaway - Dock UR Boat & Walk to Beach

Panoramic water views

Cozy Waterfront Cottage - Pet Friendly

Cliffside Bay Cottage: Pet-Friendly, Easy DC Drive
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

Clearview | an ESVR property
Private beachfront home rentals

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Waterfront South River Edgewater Sunrises & Beach!

The Oxford House

Mac's Waterfront Wonder

*Waterfront Sunset Bayview* sleeps 6

Cape St Claire waterfront getaway "The Apartment"

Country House on the Bay

• Peaceful Point • A relaxing waterfront retreat
Destinations to explore
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- Outer Banks Holiday rentals
- Hudson Valley Holiday rentals
- The Hamptons Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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