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Highland Beach Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Highland Beach vacation rentals

A building with a gabled roof and a circular vent on the roof.

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,474
￥49,675 total
includes taxes & fees
Oct 4 - Oct 5
BAYSIDE BUNGALOW
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥14,982
￥46,823 total
includes taxes & fees
Oct 5 - Oct 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

3. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is ￥31,861
￥50,468 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A wooden dock extending into a calm body of water with boats docked at the end.

4. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is ￥33,835
￥68,353 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 2br home w/ parking in downtown Annapolis
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is ￥28,604
￥80,420 total
includes taxes & fees
Oct 14 - Oct 15
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A lighthouse with a white exterior, a balcony, and a metal roof.

6. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥14,982
￥46,322 total
includes taxes & fees
Oct 4 - Oct 5
Charming Coastal/Country Home w/3 Acres & Sauna!
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

7. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is ￥60,902
￥118,046 total
includes taxes & fees
Oct 1 - Oct 2
Charming Annapolis WaterVIEW Home
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

8. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is ￥35,723
￥94,365 total
includes taxes & fees
Oct 4 - Oct 5
Renovated Bungalow | Walk to Beach | Dog-Friendly
A sunroom with a dining table, chairs, a sofa, and a chessboard.

9. Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (34 reviews)
"Great place to stay, would book it again, "
United States
Kim M.
The price is ￥47,211
￥60,817 total
includes taxes & fees
Oct 1 - Oct 2
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

10. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥15,148
￥54,088 total
includes taxes & fees
Oct 4 - Oct 5
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

11. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is ￥10,906
￥33,422 total
includes taxes & fees
Oct 12 - Oct 13
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

12. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥48,640
￥90,033 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

13. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (20 reviews)
"This was an adorable little place, perfect for my husband and I. With a few minor tweaks and upgrades, this would easily be a five star stay. I would happily stay here again. Thank you!"
United States
Deanna
The price is ￥11,173
￥18,119 total
includes taxes & fees
Oct 4 - Oct 5
Lower Level Loft - Adorable Studio Apt. Near BWI
Three birds perched on a wooden structure by the water.

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥118,028
￥208,437 total
includes taxes & fees
Oct 1 - Oct 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A house with a deck, a fire pit, and blue Adirondack chairs.

15. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is ￥40,601
￥48,479 total
includes taxes & fees
Oct 1 - Oct 2
Lakefront Home Firepit BWI Marleycreek River
A modern kitchen with dark cabinets, a white countertop, and a large window.

16. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is ￥14,163
￥42,227 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
A two-story house with a covered patio, a garage, and a well-maintained lawn.

17. 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, (55 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is ￥66,882
￥86,651 total
includes taxes & fees
Oct 19 - Oct 20
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

18. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥133,765
￥227,573 total
includes taxes & fees
Oct 5 - Oct 6
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A swimming pool with lounge chairs, a brick patio, and a house in the background.

19. Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
Severn
9.6 out of 10, Exceptional, (37 reviews)
"This was a weekend celebrating our son's retirement from the Navy. The weather and accommodations were great. The family loved the big yard, front and back, and the pool. We would gladly rent it again if we could get our whole family together."
United States
Perry S.
The price is ￥25,239
￥143,378 total
includes taxes & fees
Oct 4 - Oct 5
Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

20. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (41 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is ￥21,953
￥52,654 total
includes taxes & fees
Oct 1 - Oct 2
Large 2 bedroom house with private parking in a nice neighborhood
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The staff was welcoming and very pleasant at check in. I was able to park my car next to my room so i did not have to walk a lot together to my room. The room and amenities at this hotel is amazing! Full kitchen! Easy accred walking path to the breakfast buffet. The breakfast was excellent with healthy choices . I enjoyed my stay!!"
Esther 1-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

Find out more about Highland Beach

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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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Highland Beach vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do 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 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.