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Vacation rentals in Highland Beach

Vacation rentals in Highland Beach

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Sunny Spot Suite, Spacious & Serene,near Annapolis
    SUPERHOSTEntire guest suite · 3 guests · 1 bed · 1 bath
    Sunny Spot Suite, Spacious & Serene,near Annapolis

    Clean, bright, private and spacious basement suite in my home. Separate entrance, complete privacy and isolation. Clean, disinfected and safe. There are two rooms, both with their own access to the bathroom. There is a lovely, lush view out the back.

    What guests are saying:

    “What a great find! My girlfriend and I were on a business trip and we stumbled upon this Airbnb it was fabulous. Cute cats, amazing record collection and also a super awesome host. I took a walk around the neighborhood it was such a great surrounding and Sharon is just an awesome person.”

  • Pet Friendly Light House
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 bath
    Pet Friendly Light House

    Tons of natural light and clean floors make this dog friendly AirBnB a great place to stay. Located directly on the water and a short walk to downtown. Quiet and serene. 5 miles from the Annapolis Baltimore bike trail.

    What guests are saying:

    “We had a great time at Lee’s place. The communication was super easy and quick and the place looks exactly like it does on the pictures. We felt very comfortable, safe, and it was very clean. The location was great, too. We just loved every minute of our visit. Would absolutely recommend to stay there! Thank you Colby and Lee!!”

  • Chic Boho Flat 10 min from Downtown Annapolis
    SUPERHOSTEntire guest suite · 4 guests · 2 beds · 1 bath
    Chic Boho Flat 10 min from Downtown Annapolis

    Our chic bohemian basement level apartment offers guests their own private entrance and driveway. The open floor plan and oversized window make the flat, spacious and light. It is a quiet, homy respite, 10 minutes’ drive from Historic Downtown Annapolis. Spend your days exploring the towns rich history and taking in stunning views of the Chesapeake Bay and its tributaries. Then come home to a relaxing space. Enjoy a selection from our library or make a meal in the fully equipped kitchen.

    What guests are saying:

    “Wow! A very clean, nice place to stay. The photos are true to how it is. It is a home away from home that you look forward to going back to at the end of a day of sightseeing. Elizabeth was quick to respond to our communications and was easy to work with. We look forward to returning on another visit to the area!”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Highland Beach vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Highland Beach

Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:$55 CAD/night
Pet Friendly Light House
SUPERHOSTPrivate room
Pet Friendly Light House
Price:$62 CAD/night
NEW! Chesapeake Cottage w/Private Dock + Fire Pit!
Entire cottage
NEW! Chesapeake Cottage w/Private Dock + Fire Pit!
Price:$289 CAD/night
Simple room in apartment for single man share bath
SUPERHOSTPrivate room
Simple room in apartment for single man share bath
Price:$37 CAD/night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:$103 CAD/night
Chesapeake Bay Annapolis Retreat
Entire apartment
Chesapeake Bay Annapolis Retreat
Price:$33 CAD/night
The Magnolia in Pasadena Maryland
SUPERHOSTEntire house
The Magnolia in Pasadena Maryland
Price:$69 CAD/night
"Italia Room" Near Downtown Annapolis
SUPERHOSTPrivate room
"Italia Room" Near Downtown Annapolis
Price:$73 CAD/night
Spacious Sunny Condo Close to Convention Center
Entire condominium
Spacious Sunny Condo Close to Convention Center
Price:$67 CAD/night
Chic Boho Flat 10 min from Downtown Annapolis
SUPERHOSTEntire guest suite
Chic Boho Flat 10 min from Downtown Annapolis
Price:$103 CAD/night
Howard's Cove Retreat
Private room
Howard's Cove Retreat
Price:$90 CAD/night
Private Room Close To Baltimore & BWI + EXTRAS
SUPERHOSTPrivate room
Private Room Close To Baltimore & BWI + EXTRAS
Price:$29 CAD/night
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