Apartments in Highland Beach for Rent

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Highland Beach apartments

Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 14 - Dec 15
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (3)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
$375 nightly
The price is $428
Dec 28 - Dec 29
Total with taxes and fees
Dean Street's Lower Deck House!
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
$424 nightly
The price is $483
Jan 5 - Jan 6, 2026
Total with taxes and fees
Annapolis Gem: Stylish and Cozy
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (48)
"Perfect hideaway for a weekend trip to Annapolis. Great location and had everything we needed for the kids. Host was very accommodating and communicative, would come back!"
United States
Jay B.
$405 nightly
The price is $461
Dec 15 - Dec 16
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Beach Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Highland Beach

Highland Beach Apartments information

Number of reviews
132
Accommodation
83 Apartments
Lowest Price
$414
Highest Price
$483

Frequently asked questions

What's it like to stay at an apartment in Highland Beach?
You'll find plenty of places to stay with in Annapolis, with 558 lodging choices including 54 apartments.
Are you thinking about an apartment for your stay?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, but also for families wanting the conveniences of home.
What's a favorite apartment I should consider for a stay in Highland Beach?
Listed below are some of the favorite apartments in the area: Downtown St. Michaels | Porch + Pet-Friendly: Situated in St. Michaels, 16.3 mi/26.3 km from the heart of Highland Beach. Includes private balconies. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located 5.7 mi/9.1 km away in Annapolis. Free WiFi, sofa beds, and jetted bathtubs are included. Onsite laundry facilities and a hot tub are on site. Waterfront Oasis of Annapolis Star: Located 5.6 mi/9 km away in Annapolis. A private pool, free WiFi, and fireplaces are included. Access to an outdoor pool is available on site. Luxury Pool Loft sleeps 4: Located in Annapolis, 7.5 mi/12.1 km from Highland Beach. Includes fireplaces. Access to onsite laundry facilities is available on site.
What can I expect from the weather in Highland Beach?
Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Highland Beach. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Highland Beach is 52 inches.
What are the must-see places to visit in Highland Beach?
Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you'll find Bay Ridge Beach and Maryland Quiet Waters Park.
What's the best way to get to and around Highland Beach?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Fort Meade, MD (FME-Tipton), which is located 19.2 mi (30.9 km) away from the city center. You can also search for flights into Baltimore Washington Intl. Airport (BWI), which is 20.4 mi (32.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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