Highland Beach Vacation Rentals

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Vacation Rentals in Highland Beach

Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$288 nightly
The price is $317
Oct 30 - Oct 31
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (31)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$224 nightly
The price is $237
Oct 29 - Oct 30
Total with taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$825 nightly
The price is $910
Nov 1 - Nov 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Fridge, microwave, oven, stovetop
Annapolis Boat Life - Overnight Stays
Annapolis Boat Life - Overnight Stays
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
$317 nightly
The price is $323
Oct 30 - Oct 31
Total with taxes and fees
Annapolis Boat Life - Overnight Stays
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Oct 29 - Oct 30
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Pool
Luxury Pool Loft sleeps 4
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$330 nightly
The price is $354
Oct 29 - Oct 30
Total with taxes and fees
Luxury Pool Loft sleeps 4
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
$288 nightly
The price is $307
Oct 29 - Oct 30
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!
1 bedroom, desk, free WiFi, bed sheets
Lower Level Loft - Adorable Studio Apt. Near BWI
Lower Level Loft - Adorable Studio Apt. Near BWI
9.4 out of 10, Exceptional, (13)
"This was great for our stay. Nice place to come back to at the end of the day. It’s in a quiet neighborhood and being a lower level there is no traffic noise either. Great communication with the host and the description of the listing is accurate. Enjoy!"
United States
Jack B.
$111 nightly
The price is $127
Oct 29 - Oct 30
Total with taxes and fees
Lower Level Loft - Adorable Studio Apt. Near BWI
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$432 nightly
The price is $477
Nov 2 - Nov 3
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
$352 nightly
The price is $401
Nov 17 - Nov 18
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport
Modern New Suite Close to US Capital and BWI Airport
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
$127 nightly
The price is $144
Oct 29 - Oct 30
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport
Outdoor dining
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
Oct 29 - Oct 30
Total with taxes and fees
BAYSIDE BUNGALOW
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very Good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
$110 nightly
The price is $125
Oct 29 - Oct 30
Total with taxes and fees
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium
All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (6)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
United States
Paige R.
$622 nightly
The price is $662
Oct 29 - Oct 30
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$395 nightly
The price is $419
Nov 3 - Nov 4
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$579 nightly
The price is $660
Oct 29 - Oct 30
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Interior
40' Bristol sailboat with spectacular views
40' Bristol sailboat with spectacular views
2.0 star property
$412 nightly
The price is $437
Oct 29 - Oct 30
Total with taxes and fees
40' Bristol sailboat with spectacular views
TV, books, offices
Holly Hill Haven - Sleeps 10
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$478 nightly
The price is $509
Nov 17 - Nov 18
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$434 nightly
The price is $495
Oct 29 - Oct 30
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Property grounds
New Downtown Annapolis Condo With Free Parking
New Downtown Annapolis Condo With Free Parking
10.0 out of 10, Exceptional, (31)
"The apartment is exactly what we expected and was a great place to stay! Highly recommend. "
United States
Megan U.
$325 nightly
The price is $371
Nov 17 - Nov 18
Total with taxes and fees
New Downtown Annapolis Condo With Free Parking
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
"Lovely room"
Christopher 2-night trip
Posted 20 hours ago
Historic Inns of Annapolis

Find out more about Highland Beach

Everything you need to know about Highland Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Beach. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Beach in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Beach rentals

At Expedia, we put the best Highland Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Highland Beach?

Yes, there are vacation rentals near top local attractions in Highland Beach, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Highland Beach has to offer?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: Visitors like this Highland Beach vacation home rental. It is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Highland Beach?

Chesapeake Bay and Northern 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 a vacation rental in Highland Beach like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Highland Beach. Vacation rentals offer amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.