Apartments in Highland Beach for Rent

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Apr 10 - Apr 12

Our top choices for Highland Beach apartments

Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$361 nightly
The price is $412
Dec 17 - Dec 18
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt

Apartment in Historic District

Charming Downtown 3rd Floor 1 Bedroom Apt
9.8 out of 10, Exceptional, (20)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
$245 nightly
The price is $279
Dec 17 - Dec 18
Total with taxes and fees
Charming Downtown 3rd Floor 1 Bedroom Apt
Interior
Dean Street's Lower Deck House!

Apartment in Historic District

Dean Street's Lower Deck House!
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.
$374 nightly
The price is $427
Dec 28 - Dec 29
Total with taxes and fees
Dean Street's Lower Deck House!
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
$421 nightly
The price is $479
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

Apartment in Admiral Heights

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (48)
"Beautiful rental in a safe, walkable, convenient part of town. Very much enjoyed our stay! Was a perfect place to stay for out trip to the Renaissance Festival. Got to stay in town with no rush to get home!"
United States
Mary G.
$405 nightly
The price is $461
Dec 17 - Dec 18
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Fridge, microwave, oven, stovetop
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Apartment in Historic District

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (27)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
United States
betsy b.
$271 nightly
The price is $309
Dec 28 - Dec 29
Total with taxes and fees
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening "
Teresa 2-night trip
Posted 23 hours ago
Hilton Garden Inn Kent Island Marina

Find out more about Highland Beach

Highland Beach Apartments information

Number of reviews
177
Accommodation
83 Apartments
Lowest Price
$279
Highest Price
$479

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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