Beachfront vacation rentals in Highland Beach

We had an incredible stay with our two dogs. Beautiful property and views. The interior is very comfortable, and Chip goes above and beyond with ensuring that little creature comforts are available, like make-up wipes, coffee creamer, and smores supplies. We even found a tiger shark tooth down by the beach! A few notes that didn’t impact our stay, but some may find useful: -There is a partial fence around the home. It serves as a barrier to prevent you from stumbling down a slope, but won’t fully contain dogs or kiddos. This wasn’t an issue for us as the screened in porch was convenient to leash dogs, and the fence served as a visual barrier for them so they didn’t get distracted during quick potty breaks. -The garage is very well stocked with games and toys. There is no interior access and you must enter through the main garage doors, which may impact the needed supervision of kiddos. Overall amazing place, would definitely visit again!!

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!

Very thankful for Danielle’s hospitality and flexibility! We were a last minute booking and had to extend more than once while waiting on movers for our home, and Danielle was ultra helpful in the process. The house was clean, cute, and in a great location for beach visitors. We will absolutely be checking to make sure either the Lazy Crab or Blue Crab are available when we plan to visit the area again! After a cross country trip that consisted of several underwhelming hotels and stays along the way, Danielle’s property was a much needed refresher for my family!

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.

This is easily one of the nicest and most well-appointed Air BnBs we have ever stayed at. We appreciated the unit being stocked with eggs, wine, NA beverages, coffee, butter, snacks, and other local goodies. The house itself was awesome!!! The views of the bay were indescribable. We loved using the hot tub, fire pit, fishing, and kayaking to the nearby sandy beach. There wasn’t a ton to do in the neighboring towns but there was no reason not to hang out near the water. There were great restaurants, a couple cute thrift stores, and a nice grocery store which had everything we needed. We bought fresh caught oysters down the road and had fun trying our hand at cooking them.

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!

The experience was once in a lifetime and was something that I would look forward to doing again. It was close to DC Baltimore and other metropolitan area.

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.

This was one of the best stays I've had through Air BnB. Everything you need was available. Plenty of towels and toiletries. Beautiful Location in view of the water. Paul, the host was responsive and accomdating. Will be staying here in the future to take advantage of water sport activities provided!

We had a wonderful family thanksgiving! The kitchen was perfect for our needs!

Absolutely fabulous experience! We stayed during a very low key time (Christmas+) but were able to find lots of fun things to do (shopping in St Michael’s [don’t miss The Blue Heron for the best caffeine], driving tour of Blackwater National Wildlife Refuge, etc.). We got incredible photos during sunrise/sunset, safely walked-ran on the neighborhood roads, enjoyed the fire pit, and thoroughly rested and relaxed. So grateful we chose Jon’s home for 5 days/4 nights of R&R ❤️

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 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 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!

Our stay at this beautiful waterfront property in Annapolis was nothing short of perfect. The home had everything we needed to rest and relax with family, offering stunning views and a peaceful atmosphere. From the cozy furnishings to the well-equipped amenities, it truly felt like a home away from home for our quick weekend getaway. We couldn’t have asked for a better place to unwind, and we’ll definitely be back!

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.

We were welcomed into a beautiful, cozy and warm cottage with spacious living space and gorgeous kitchen. The bedrooms and bathrooms were spotless and inviting. The cottage was a short walk from the community beach and a small playground. It was less than a 15 min drive into downtown Annapolis where we spent two lovely afternoons perusing stores and historic homes. We would definitely go back to this home. P.S. It was the easiest check out possible.

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!