Beachfront vacation rentals in Highland Beach

Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!

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.

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!

My wife, baby daughter and myself came here for our spring break. The views from apartment were spectacular and we enjoyed watching the boats coming and going. Maria was a gracious host and gave us lots of fantastic local recommendations. The apartment was clean and comfortable and the kitchen was well stocked for us to use. We loved our stay here, and will try and come back on the future.

We just had another wonderful stay at the Cozy Cottage in North Beach. The house is just lovely and quite comfortable. Our dog Frankie certainly felt as relaxed as we did. The view from the large front window is just great. The Chesapeake Bay, and all the dog walkers on the boardwalk are just amazing. Jerome and Carrie are always friendly, responsive and accomodating. Last, but not least, we can't wait to go back.

We had a peaceful and relaxing stay at Joel’s home. The house and the grounds overlooking the waterfront were beautiful: We watched both sunrises and sunsets from the dock overlooking the bay, chatted with friends out on the screened-in porch and enjoyed evening fires by the outdoor fire-pit. The kitchen had more than everything we needed to cook, but there were also great restaurants just a 10-15 minute drive away. Whether we were inside or outside the house, we had sweeping views of the bay; there were so many windows to let the light in! We thoroughly enjoyed our stay, and look forward to visiting again!

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.

Andy was an awesome host! He checked in with us in the mornings to see if we needed anything (via text). They also had some great recommendations for us since we were out-of-towners. Would not hesitate to book with Alice and Andy again if we are ever in the area!

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!

A nice peaceful place to stay. Easy to get into town. A little tricky to find the first turn off the main road, but once you see the sign it makes sense. Would bring everything you need including ingredients to cook (sugar for coffee, salt, etc). But cleaning supplies are there and it's all very comfortable.

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.🥰

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.

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.

I have stayed here several times and I am always impressed with how clean and comfortable the place is and how she makes you feel at home. She goes above and beyond anywhere else I have ever stayed at. They have thought of everything you might want or need to make you stay a warm and pleasant memory . She is a gracious hoist and makes sure your stay is a wonderful experience. I love stay there. I have already booked a future trip there.

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!

Lisa and Jim’s place is fantastic! Just as advertised. Their communication was next level! Highly recommend!

Joanna was an excellent host, and the home was such a beautiful, quiet retreat for our family while we were attending a wedding in the area. The home was beautiful and cozy, and the scenery outside was so calming. We wished we could have stayed longer, and we hope to book again for fun some other time!

A wonderful stay at this Airbnb! The place was spotless and had everything you would need. It was incredibly comfortable, and you feel right at home throughout the stay. Communication with the owners with seamless - they were quick to respond! Highly recommend the spot for anyone looking for a cozy inconvenient place to stay!