
Beachfront holiday rental in Highland Beach
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Top-rated beachfront accommodation in Highland Beach
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
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Popular amenities for Highland Beach beachfront rentals
Pet-friendly beachfront home rentals

A Little Piece of Paradise - Waterfront Home
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!!

Chesapeake Houseboat Getaway
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.

Wonderful Cottage Nestled On Chesapeake Bay
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.

Little Slice of Cambridge. Newly listed, 2 bedroom
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.

Shewell’s Cottage by the Shore
What a gem of a place! So cute and cozy. A great location! Loved all the natural light that came in through the big windows. Everything was so clean yet very comfortable. Enjoyed walking the beach. Found sharks teeth and sea glass! Such a great surprise to find such treasures! Lisa was so very kind and accommodating. Appreciated the extras like coffee, bottled water, shampoo etc and she brought some wood for a cozy fire. They really worked hard at making our stay very comfortable. Definitely will be coming back. But plan on a longer stay because there is so much more in the area to check out!

Panoramic water views
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.

Cozy Waterfront Cottage - Pet Friendly
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

Bay Home in Annapolis with Private Dock
Beautiful place, beautiful location. Joel thought of anything you could want.
Beachfront home rentals with a pool

Chestertown Watson Family Farm
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.

Waterfront Escape with Pool Nature Lover Paradise
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%

Turtle's Nest - Hist. Cambridge
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

Private Waterfront Cottage on Bolingbroke Creek
Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI
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.

"Endless Summer" on the Chesapeake!
great location and very clean!

10 Minutes to St. Michaels with a Private Pool
This place is really great. The house is as described and very comfortable, but the star is the yards. The back yard goes right up to the water, has a pool and a grill, and is large. The front yard is even bigger and has a lovely kid swing under a tree. Definitely a great place to come if you want to spend a lot of time outside playing or looking out over the water.

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
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!
Private beachfront home rentals

Bay View Beach Cottage, perfect for long-term
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.

Adorable 1 BR guest house with water views, deck
Clean and cute and just as described. Perfect for a long weekend away in Annapolis for the boat show!

Bayside Bungalow: Cozy North Beach Getaway
Perfect getaway spot on North Beach! Location, location, location!! Walkable to boardwalk, pier, great restaurants and shops. Although it is an older home it has been nicely renovated and we especially loved the front porch where we spent our time relaxing in the morning before we headed out for the day. Extremely responsive host! 5 Star Stay! We would not hesitate to book again!

CoastalBeachCottage*BayViews*Close2WeddingVenues
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.

Chesapeake Beach Charm: Cozy Home with Bay views
We had a beautiful stay. It was exactly what we needed.

Quaint Waterfront- access, Private Shorehouse-unit
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!

Bahia Breeze - Beachfront Cottage
This was a cute little home to stay at over the weekend. Only downside was having to pay for beach access. But the house itself was very nice and had all the kitchen items we needed. Would stay again.

Beachfront camping under the stars
Super fun place really peaceful The house was super nice. I loved waking up in the morning and seeing the sunrise.😁🫶🏻
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Hampden
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Congressional Country Club
- Crystal Beach Manor, Earleville, MD