Beachfront holiday rentals in Highland Beach

Lauren is an excellent host. The property was wonderful, clean and suit our needs. The perfect top it off was… there were adequate chips, and fritters - just after we drove in the house.👌 I was a bit hungry, and gave me some time to get my essentials for the stay - which, btw…wasn’t too far. It had a nice walk to the small beach, and we thoroughly enjoyed it. Lastly, Lauren was exceptional with our request for a late check out. Thank you. Definitely a 5 star! Will definitely stay at this same place, again. Regards Bala

It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!

I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.

The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.

We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.

Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !

This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.

This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back

We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!

Hosted my intimate wedding at Nancy’s home and we had an amazing weekend! My family & closest friends loved the home, location, amenities & the coziness of the house. Perfect for a lil vacation with friends & family and very kid friendly. Absolutely loved my stay. Thanks for letting us stay at your place, view was incredible and so much space for a big group. Will definitely come back and recommend 100%

We had a fantastic stay at this Chesapeake Bay home for our annual family trip! The outdoor space is a total standout—beautiful views, a great pool, and everything we needed for kayaking, crabbing, and making memories by the water. We especially loved the roomy layout, the well-stocked kitchen, and the big dining table that made family dinners a highlight each night. The house is full of personality, with tons of unique decor and interesting items throughout—definitely made for a fun and memorable stay, though we did find ourselves having to keep a very close eye on the kids around all the treasures! Overall, it was a wonderful trip and we’d absolutely book again!

A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.

great location and very clean!

This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

A great place to enjoy a long weekend at the Eastern shore in Maryland.

Susan’s place was perfect for my parents’ extended stay with beautiful views of the Chesapeake out the windows and access from a lovely beach. My dad felt right at home going for his daily walks and meeting all the dogs in the neighborhood. The location is super convenient to a grocery store and selection of restaurants as well as getting into downtown Annapolis. The kitchen is well equipped and beds are great. Susan was incredibly communicative and very accommodating in extending the stay beyond their original booking.

This place is nicely furnished and the kitchen/dining area are very well supplied. We always enjoy our time in Oxford and the surrounding area and Suzanne Marie's place made it very comfortable. Walkable to the market, coffee shop, ice cream shop and 2 restaurants.

We had a wonderful visit to North Beach staying at William's bayside bungalow! The location is absolutely perfect. The bungalow is steps away from the boardwalk and conveniently located to the beach and all the fun shops in town. The bungalow was comfortable and perfect for our trip. We especially loved sitting on the front porch and enjoying the view of the bay. William was a gracious and communicative host. We'd be excited to stay here again in the future!

Michelle’s place is super cute! It’s also got more space inside than you may expect from the front view of the home. It’s got a cute upstairs space that does add to the livable area of the home for guests. We enjoyed the closeness to the water and nearby wedding venue as we were guests at a friend’s wedding in Kent Island a mere 10 minutes away. It was the right place for what we needed as a family of mom, dad & 2 of our grown kids.

We had a beautiful stay. It was exactly what we needed.

Lisa and Jim were two of the loveliest hosts we've had through Airbnb. They even made us a breakfast casserole which was delicious. The house is conveniently located and was very comfortable for our family of three. The kitchen was stocked with everything we needed and there were the basics like coffee and sugar. If you like the great outdoors, this area of Maryland is wonderful. Thank you Lisa and Jim!

We had such a wonderful time staying at this airbnb! My partner and I can for a relaxing weekend away and this place definitely delivered! the cottage was adorable and just as pictured, and the location was perfect! we spent much of our time in the lovely shared yard space, watching the sunset, barbecuing, and sitting by the fire, and we took out a canoe for hours on the water - such a nice perk that these were provided! the hosts were so welcoming and always eager to help! I would love to come stay again

My family had a wonderful stay at this beautiful cottage. It is beautifully furnished and modern. The screened in porch was so wonderful to sit and look out on the river. Everything was so organized from check in and check out- and everything in between!