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Highland Beach Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Highland Beach holiday rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is HK$831
HK$2,436 total
includes taxes & fees
26 Oct - 27 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A wooden dock extending into a calm body of water with boats docked at the end.

2. 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 HK$1,962
HK$3,785 total
includes taxes & fees
2 Nov - 3 Nov
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

3. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Great property. Big back yard. Nice walk to downtown and campus."
United States
Stephen P.
The price is HK$2,574
HK$6,254 total
includes taxes & fees
27 Oct - 28 Oct
Eastport 3 bedroom Cottage: Walk to Downtown
A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

4. 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.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A two-story house with a covered patio, a garage, and a well-maintained lawn.

5. 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)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is HK$3,002
HK$3,887 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A beach with chairs and a pier in the background.

6. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$1,766
HK$4,089 total
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A lighthouse with a white exterior, a balcony, and a metal roof.

7. 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 stay"
United States
Michael V.
The price is HK$752
HK$2,340 total
includes taxes & fees
25 Oct - 26 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

8. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"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.
The price is HK$1,750
HK$3,883 total
includes taxes & fees
26 Oct - 27 Oct
Dean Street's Lower Deck House!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,900
HK$5,557 total
includes taxes & fees
22 Oct - 23 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern office space with a desk, computer, and ergonomic chair.

10. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is HK$1,460
HK$4,901 total
includes taxes & fees
26 Oct - 27 Oct
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

11. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
United States
Amy T.
The price is HK$1,460
HK$4,437 total
includes taxes & fees
27 Oct - 28 Oct
Historic Row Home in Downtown Annapolis
A calm lake with a sandy shore, surrounded by trees and houses.

12. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is HK$1,900
HK$5,852 total
includes taxes & fees
22 Oct - 23 Oct
Londontowne Home | Beach | 3BR
A bathroom with a sink, toilet, bathtub, and shower curtain.

13. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
The price is HK$1,397
HK$3,836 total
includes taxes & fees
4 Nov - 5 Nov
Chapel Gate 3BR Steps to City Dock & Naval Academy
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

14. 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 HK$1,512
HK$4,354 total
includes taxes & fees
22 Oct - 23 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

15. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,475
HK$4,070 total
includes taxes & fees
2 Nov - 3 Nov
Upscale Condo in Annapolis w/Private Parking
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

16. 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, (28 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is HK$516
HK$1,635 total
includes taxes & fees
28 Oct - 29 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
Stylish kitchen with open layout and island seating

17. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$1,640
HK$3,981 total
includes taxes & fees
27 Oct - 28 Oct
Pool Loft Suite | Bay Access & Beach Passes
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

18. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
The price is HK$1,554
HK$9,895 total
includes taxes & fees
27 Oct - 28 Oct
Luxe Row Home Steps to USNA Gate 3!
Interior

19. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is HK$1,585
HK$4,563 total
includes taxes & fees
3 Nov - 4 Nov
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A modern kitchen with a central island, built-in oven, and microwave.

20. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is HK$1,554
HK$4,069 total
includes taxes & fees
27 Oct - 28 Oct
Cute bungalow blocks to Stadium
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
"Charm & History merge in quiet elegance."
Joshua 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Highland Beach

Search for holiday rentals in Highland Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Beach using one of the methods below:

  • View our selection of featured holiday rentals in Highland Beach
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Look no further and take a look at our great range of rental properties in Highland Beach!

Frequently asked questions

Can I find a holiday rental in Highland Beach?

Yes, there are holiday rentals close to the most popular sights in Highland Beach, or you can select a more secluded option if you're looking for a relaxing stay.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Highland Beach is located near the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Bay Ridge Beach and Maryland Quiet Waters Park.

What’s a holiday rental in Highland Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland Beach. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family trip.