Holiday Rentals in Highland Beach
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Holiday Rentals in Highland Beach

The Heron's Nest at Atlantic Marina

Waterfront Oasis of Annapolis Star

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Floating 2 bed 2 bath condo stunning views of the bay

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Chesapeake Houseboat Getaway on Kent Island, Maryland

Edgewater/Mayo Getaway!

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Secluded Tiny House -Private Pool -Self Check in

Relax on Kent Island in 3 Bedroom Home w/Waterview

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Romantic Two Bedroom Condo

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Blue Crab Beach House - Free beach passes
Other types of properties in Highland Beach you may be interested in

Historic Inns of Annapolis
Holiday Accommodation Highland Beach
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Highland Beach are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Highland Beach itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Highland Beach holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Highland Beach, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Highland Beach with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.