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Highland Beach Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Highland Beach vacation rentals

Exterior

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, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AED 514
AED 1,237 total
includes taxes & fees
24 Aug - 25 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior

2. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AED 657
AED 2,001 total
includes taxes & fees
15 Sep - 16 Sep
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

3. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AED 633
AED 1,773 total
includes taxes & fees
24 Aug - 25 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is AED 407
AED 1,133 total
includes taxes & fees
18 Aug - 19 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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 AED 837
AED 2,236 total
includes taxes & fees
1 Sep - 2 Sep
Renovated Bungalow | Walk to Beach | Dog-Friendly
Outdoor dining

6. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 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 AED 1,223
AED 2,500 total
includes taxes & fees
14 Sep - 15 Sep
Charming Annapolis WaterVIEW Home
Beach nearby, sun loungers, beach towels

7. 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, (18 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,190
AED 2,387 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Living area

8. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AED 905
AED 2,376 total
includes taxes & fees
19 Aug - 20 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Marina

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (84 reviews)
"Thank you for the stay! We loved the location."
United States
Mary G.
The price is AED 882
AED 1,725 total
includes taxes & fees
17 Aug - 18 Aug
Cozy 2br home w/ parking in downtown Annapolis
Exterior detail

10. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is AED 370
AED 1,084 total
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Exterior detail

11. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AED 800
AED 2,001 total
includes taxes & fees
17 Aug - 18 Aug
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Dining

12. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is AED 683
AED 2,085 total
includes taxes & fees
17 Aug - 18 Aug
Historic Row Home in Downtown Annapolis
Coffee/tea maker, fridge, microwave, stovetop

13. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 711
AED 1,455 total
includes taxes & fees
17 Aug - 18 Aug
Waterfront Oasis of Annapolis Star
Interior

14. 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 AED 650
AED 2,014 total
includes taxes & fees
17 Aug - 18 Aug
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Coffee/tea maker, fridge, microwave, oven

15. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AED 760
AED 1,959 total
includes taxes & fees
18 Aug - 19 Aug
Cute bungalow blocks to Stadium
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 889
AED 2,601 total
includes taxes & fees
17 Aug - 18 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Interior

17. New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking
Historic District
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful property, excellent location, and had a wonderful visit to Annapolis!"
United States
Darby F.
The price is AED 694
AED 1,549 total
includes taxes & fees
31 Aug - 1 Sep
New Downtown Annapolis Condo With Free Parking
Coffee/tea maker, fridge, microwave, oven

18. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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 AED 707
AED 1,795 total
includes taxes & fees
17 Aug - 18 Aug
Pool Loft Suite | Bay Access & Beach Passes
Interior

19. 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 AED 806
AED 1,723 total
includes taxes & fees
31 Aug - 1 Sep
Dean Street's Lower Deck House!
Coffee/tea maker, fridge, microwave, oven

20. 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 AED 962
AED 2,667 total
includes taxes & fees
17 Aug - 18 Aug
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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
"Unique and historic hotel with quaint rooms and well decorated period common spaces. Friendly staff and very clean."
Frank 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

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 Maryland Quiet Waters Park and Annapolis Landing Marina.

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.