Holiday Rentals in Highland Beach

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Holiday Rentals in Highland Beach

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (84)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Fridge, microwave, oven, stovetop

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Terrace/patio

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (33)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is €238
includes taxes & fees
12 Jan - 13 Jan
Relax on Kent Island in 3 Bedroom Home w/Waterview
Freshly renovated 3-story home 1 block from USNA!
Fridge, microwave, oven, stovetop

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (28)
"What a fantastic location, central to everything in the city. Parked the car and walked everywhere. The house is perfect!!"
The price is €632
includes taxes & fees
12 Jan - 13 Jan
Freshly renovated 3-story home 1 block from USNA!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (207)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (48)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (77)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

9.4 out of 10, Exceptional, (13)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (41)
"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...
The Lazy Crab Beach House - Free beach passes
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (103)
"Awesome House Awesome neighborhood Awesome Host(ess). 10 out of 10"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (56)
"This house is so cute and comfortable. Everything was perfect and better than described. It is within walking distance of some delicious restaurants. Our host was amazing and answered all questions very quickly."
Recently Renovated Annapolis Home - Conveniently Located
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (50)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (33)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
USNA Quintessential Charm ~ Downtown Annapolis.
Smart TV, books

USNA Quintessential Charm ~ Downtown Annapolis.

9.8 out of 10, Exceptional, (7)
"We really enjoyed this property. It was clean and tidy. Checking in was simple. Parking was straightforward once we noticed the markers giving us clear instructions. The kitchen has everything you need. I stayed in the downstairs bedroom, and the bed and pillows were very comfortable. The downstairs shower is small, but the water pressure is good. Everyone who stayed upstairs enjoyed the amenities. Definitely will try to rent this again for the next time we visit Annapolis."
The price is €433
includes taxes & fees
6 Feb - 7 Feb
USNA Quintessential Charm ~ Downtown Annapolis.
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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Other types of properties in Highland Beach you may be interested in

Crowne Plaza Annapolis, an IHG Hotel
Pool

Crowne Plaza Annapolis, an IHG Hotel

3.5 star property
8.8 out of 10, Excellent, (1003)
"staff, location and breakfast was amazing. Bummed hot tube wasnt working but hopefully next time. Room clean and comfortable "
The price is €116
includes taxes & fees
13 Jan - 14 Jan
Crowne Plaza Annapolis, an IHG Hotel
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1005)
"Great stay like always "
The price is €142
includes taxes & fees
4 Feb - 5 Feb
Graduate by Hilton Annapolis
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1722)
"Beautiful historical inn. Easy walking to a multitude of dining options. Very quiet little town!!"
The price is €202
includes taxes & fees
12 Jan - 13 Jan
Historic Inns of Annapolis
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.

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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Highland Beach is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Maryland Quiet Waters Park. In the wider area, you’ll find Spa Creek and Ego Alley.

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.