Beachfront vacation rentals in Highland Beach

Lauren’s place was very nice and accommodating for our family Christmas get together. She was very responsive and offered to help out with anything we needed while at the property. The place had the equipment we needed for cooking and serving meals throughout the stay!

A great find, and just what we needed! It was perfect for my husband, myself and our teenage son. We took the upstairs bedroom and he had the downstairs bedroom. We loved the fire pit outside and having a front row seat to the bay. The house was quaint and just perfect for the three of us. We enjoyed walking around North Beach, and also enjoyed a couple of their great restaurants, even in the off season!

Christina's place was amazing. A perfect home away from home. Super clean, peaceful, and scenic. The check-in/out process was simple and smooth. 10 out of 10. I'd stay here again in a heartbeat.

We had a winter visit and despite it being freezing outside the house was nice and toasty and we appreciated the fast hot water for showering. No fenced yard for our dog but it's a nice area to walk around. Central location, close to restaurants. Would stay again.

Beautiful, clean home ! Nice new appliances and comfortable stay !

We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!

Our family had an excellent visit over Easter. We had 4 adults and 5 children and the house was perfect for us. Amazing water views, spotless house, with great amenities and supplies. Was super helpful to have all towels and linens provided and a well stocked kitchen! The dock was great for kids to fish off and the beach was in close walking distance with a playground and other fun activities. The views were spectacular and location was about a 12 minute drive to beautiful downtown Annapolis. Highly recommend!

An extraordinary place to rest & recharge. The views, the comfort of the home, and the gorgeous walking trails, through woods & beach are a perfect combination. Everything we needed & then some.

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!

We had a great weekend a gain. Enjoying Christmas in St Michaels. Your home is beautiful. We ate at Ava’s, Limoncello, Carpenters and Talbots. Shopped on Sunday. Highly recommend the house tour. She you again soon.🥰

A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

fantastic spot on the Island. incredible sunsets. very clean with stunning views of the Bay. everything you need to enjoy the Island is here with walking distance general store.

Beautiful property with stunning views! plenty of room for everyone! It is a perfect place for kids. I was shocked at how clean and well stocked the kitchen was. We cooked breakfast every morning for 11 and Thanksgiving dinner for 25 with ease. I would definitely stay here again

We were in and out alot as were in Annapolis for a family baptism. The accommodations were wonderful. We had no problems.

We had an amazing time at Rhonda’s! Although it was a rainy weekend, there was still so much to do around the area and in the suite. Everything we needed (and more) was readily available for us. The suite was spacious, private and clean. Directions were very clear, making check-in a smooth process. Look forward to returning sometime this summer!

We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.

We had a lovely stay at Heather’s place. The house was clean, comfortable, and we felt taken care of. The porch with the view of the water and sunrises was so relaxing. Visiting during the off-season was peaceful, but there was still plenty to do in the area. We couldn’t have asked for a better getaway weekend.

Great stay! We will be back again.

Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!

I was staying at Yen’s place with my family and we had a amazing experience. The house is very beautiful with a beautiful landscape view. She was very responsive and kind. She helped us in any way she could. I would definitely recommend her place to anyone looking for a place to stay in Maryland.

This house was perfect for our family—wonderful location, big and beautiful outdoor space, all of the amenities our family needed during our stay. Steve is a wonderful host—kind, excellent communicator, and highly responsive. Ten out of ten experience!