Vacation Rentals in Highland Beach, MD
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NEW listing- New, waterfront, private house 5BR 4 BA
10
Excellent
·
Annapolis
·
5 br
·
Sleeps 10
·
Air Conditioning · Dishwasher · Balcony ·
From
$650/nightProperty
House · 5 Beds · 4 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Garage Parking
Fitness Center
Other spaces
Balcony, Kitchen, Workspace
Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.8
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Air Conditioning · High Ceilings · Fireplace ·
From
$555/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
High Ceilings
Fireplace
Beach
Waterfront
Furnished
Central Heat
In Unit Laundry
Other spaces
Kitchen
Private Apartment - Minutes to USNA
9.8
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Oven · Furnished · Kitchen ·
From
$125/nightProperty
House · 2 Beds · 1 bath
Amenities
Oven
Furnished
Other spaces
Kitchen
Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.8
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Outdoor Space · Toiletries · Beach ·
From
$200/nightProperty
House · 3 Beds · 2 baths
Amenities
Toiletries
Beach
Waterfront
Central Heat
Wifi
Tv
Free Parking
Other spaces
Kitchen
Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.7
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Outdoor Space · Beach · Furnished ·
From
$268/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Beach
Furnished
In Unit Laundry
Wifi
Free Parking
Residents Lounge
Other spaces
Kitchen
Nantucket on the Chesapeake Heated Pool
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Outdoor Space · Pool · Air Conditioning ·
From
$1,592/nightProperty
House · 4 Beds · 3 baths
Amenities
Pool
Air Conditioning
Dishwasher
Private Pool
Beach
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
DISCOUNTED FOR USNA COMMISSIONING WEEK 2023 and USNA parents weekend 2021-5..
No reviews
·
Annapolis
·
3 br
·
Sleeps 10
·
Outdoor Space · Pool · Air Conditioning ·
From
$643/nightProperty
House · 3 Beds · 3 baths
Amenities
Pool
Air Conditioning
Ceiling Fan
Fitness Center
Fireplace
Dishwasher
Beach
Waterfront
Other spaces
Kitchen, Workspace
Behold your perfect Annapolis getaway home! Gorgeous 4 bdrm, 2.5 bath with breathtaking views of the Chesapeake Bay
No reviews
·
Annapolis
·
4 br
·
Sleeps 8
·
Pool · Air Conditioning · Fireplace ·
From
$1,771/nightProperty
House · 4 Beds · 3 baths
Amenities
Pool
Air Conditioning
Fireplace
Private Pool
Waterfront
Furnished
In Unit Laundry
Swimming Pool
Other spaces
Kitchen
The best of Zumper, delivered
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Bright and cheery home. Just a short 2 blocks from the beach.
No reviews
·
Annapolis
·
2 br
·
Sleeps 5
·
Pool · Air Conditioning · Dishwasher ·
From
$99/nightProperty
House · 2 Beds · 2 baths
Amenities
Pool
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Oven
Garage Parking
Swimming Pool
Other spaces
Kitchen
Annapolis Family Vacation Rental: Close to downtown and the Naval Academy
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 9
·
Outdoor Space · Air Conditioning · Fireplace ·
From
$900/nightProperty
House · 4 Beds · 4 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Fitness Center
Other spaces
Kitchen, Workspace
Indulge or be still near Naval Academy/ Annapolis
No reviews
·
Annapolis
·
2 br
·
Sleeps 4
·
Outdoor Space · Pool · Furnished ·
From
$173/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Pool
Furnished
In Unit Laundry
Hot Tub
Wifi
Swimming Pool
Other spaces
Kitchen
Sea Glass House by the Bay - Chesapeake cottage close to the Bay beaches
No reviews
·
Annapolis
·
5 br
·
Sleeps 10
·
Air Conditioning · Assigned Parking · Dishwasher ·
From
$748/nightProperty
House · 5 Beds · 2 baths
Amenities
Air Conditioning
Assigned Parking
Dishwasher
Hardwood Floor
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
Newly-renovated home in Bay Ridge, exclusive water-privileged community
No reviews
·
Annapolis
·
5 br
·
Outdoor Space · On Site Laundry · Air Conditioning ·
From
$507/nightProperty
House · 5 Beds · 4 baths
Amenities
On Site Laundry
Air Conditioning
Fitness Center
Dishwasher
Beach
Furnished
Walk In Closets
In Unit Laundry
Other spaces
Kitchen
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
10
Excellent
·
Annapolis
·
6 br
·
Sleeps 16
·
Air Conditioning · Fireplace · Dishwasher ·
From
$679/nightProperty
House · 6 Beds · 5 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Hardwood Floor
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
3-story dog-friendly home near beaches with home theatre, grill, gaming tables
10
Excellent
·
Annapolis
·
6 br
·
Sleeps 15
·
Air Conditioning · Fireplace · Dishwasher ·
From
$974/nightProperty
House · 6 Beds · 7 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Swimming Pool
Other spaces
Deck, Kitchen
Charming Annapolis WaterVIEW Home
9.5
Excellent
·
Annapolis
·
4 br
·
Sleeps 13
·
Outdoor Space · Air Conditioning · Fitness Center ·
From
$456/nightProperty
House · 4 Beds · 4 baths
Amenities
Air Conditioning
Fitness Center
High Ceilings
Dishwasher
Hardwood Floor
Furnished
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Water Views - Close to Downtown Annapolis
10
Excellent
·
Annapolis
·
5 br
·
Sleeps 12
·
Outdoor Space · Air Conditioning · Dishwasher ·
From
$477/nightProperty
House · 5 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Kitchen
Beachfront Beauty on the Bay - A view never forgotten - 4 miles to Naval Academy
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Air Conditioning · Assigned Parking · Dishwasher ·
From
$615/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Assigned Parking
Dishwasher
Hardwood Floor
Carpet
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
WATERFRONT Historic Home on the Chesapeake Bay
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 9
·
Outdoor Space · Air Conditioning · Dishwasher ·
From
$800/nightProperty
House · 4 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Residents Lounge
Other spaces
Kitchen
Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleeps 16!!
10
Excellent
·
Annapolis
·
5 br
·
Sleeps 16
·
Dishwasher · Waterfront · Furnished ·
From
$1,026/nightProperty
House · 5 Beds · 4 baths
Amenities
Dishwasher
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
Waterfront Cottage by the Bay all one level in family-friendly community
9.7
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Outdoor Space · Air Conditioning · Fitness Center ·
From
$256/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Fitness Center
Fireplace
Dishwasher
Beach
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen, Workspace
Private Cottage on gated estate
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 5
·
Air Conditioning · Dishwasher · Furnished ·
From
$200/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis
9.9
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · Dishwasher ·
From
$259/nightProperty
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
Beach
Furnished
In Unit Laundry
Wifi
Oven
Residents Lounge
Other spaces
Kitchen, Workspace
Relaxing Bay Ridge Lagoon
9.9
Excellent
·
Annapolis
·
4 br
·
Sleeps 10
·
Outdoor Space · Pool · Air Conditioning ·
From
$1,159/nightProperty
House · 4 Beds · 3 baths
Amenities
Pool
Air Conditioning
Fireplace
Dishwasher
Private Pool
Hardwood Floor
Furnished
In Unit Laundry
Other spaces
Kitchen
Updated: March 21, 2023
Learn about vacation rentals in
Highland Beach
Vacation Rentals in Highland Beach, MD FAQ
How many vacation rentals in Highland Beach are available?
There are currently no vacation rentals in Highland Beach available. Our vacation rentals in Highland Beach include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Highland Beach?
No, right now there are no pet friendly vacation rentals in Highland Beach. A pet friendly vacation rental in Highland Beach means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Highland Beach with a pool?
No there are no vacation rentals with a pool available in Highland Beach, MD. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Highland Beach with internet access?
As of March 21, 2023, there are no vacation rentals with internet access available in Highland Beach, Maryland. Check out more enjoyable destinations on Vacations by Zumper.
