Holiday rentals with beach access in Annapolis

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Ebony is one of the best hosts I’ve ever had through Airbnb. Very responsive and helpful! You want crab at 10pm? She’ll find it for you! The view from the home was gorgeous. Very nice and quiet which allowed us some relaxation. Pleasantly surprised by the fireflies in the backyard and the huge magnolias on the tree (neither can be found in Montana where we came from). Great place. Would stay again if I ever return to the area!

This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.

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.

Sherril’s Bayside Oasis is an absolutely beautiful studio apt!!! It was spotless, comfy, and uniquely decorated. The location is convenient to the beach and within walking distance to plenty of shops and great restaurants and bars. Everything was smooth from check-in to departure. We had a wonderful stay and will most definitely check the availability of this rental when we visit North Beach again.

Fantastic getaway, perfect for a couples trip! Kathleen’s attention to detail was unlike any other Airbnb host I’ve experienced - from a stocked fridge, binder of recommendations, bathroom essentials, and more - she truly thought of everything! We would absolutely stay again. The home was spotless and the small beach in the neighborhood is lovely to spend a sunny day outside!

We really enjoyed our stay at Maria’s place! Everything was comfortable, clean, and convenient. The house has character and charm while also being modern with a luxurious feel to it. We walked to and highly recommend the Bakist for coffee and breakfast!

Deborah was an amazing host, super responsive and incredibly kind. The room was spacious, and we absolutely loved it. Everything was perfect!

We were in town for a wedding and this home was as described and was perfect for our family of 8 that stayed here. The neighborhood was quiet and peaceful. I wish we had time to enjoy the views from the lake. John was a great host and communicated with us throughout our stay. I would recommend this home to anyone who is looking to stay in the Riviera Beach or Pasadena area. It was close to everything we needed during our stay including the airport.

Beautiful home and exactly as advertised. Joseph was responsive and proactive and very friendly. The house was clean, quiet, and perfect for what we needed- a comfortable night's sleep and space for a family with pets. Everything went smoothly and met our expectations. Would rent again.

Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!

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.

Absolutely loved our time here. The owner has thought of everything. The entire house is well appointed. Kitchen has all you need to cook for a family. Multiple high quality TVs throughout. Beds are comfortable and plentiful sleeping arrangements for a larger group. Nice little town with a lot of charm. Convenient short drive to the Naval Academy. Neighborhood is quiet and private. Backyard is impressive, screened in patio is unique and comfortable. We’ve stayed at multiple Airbnb’s in Annapolis and this one tops our list. Host is fantastic, she worked with us on an early check in which was super helpful.

Ruby on the bay lives up to its name. Such beautiful surroundings - loved being on the deck hearing the wind in the pines. I was grateful to unplug! Excellent size for my sister, me and our fur bosses. Could have comfortably fit 2 - 3 more adults. Nikki was instantly responsive & informative. I would love to return.

I stayed at this Airbnb over the past weekend and had such a wonderful time! The house was clean, welcoming, and had everything we needed to feel right at home. My favorite part was definitely the dock and the little beach area behind the house. I spent hours lounging on the beach chairs, soaking up the sun, and listening to the waves — so relaxing. It was a bit early in the season to really go crabbing, but I had a blast learning how to set the traps. We even caught one little crab and let him go — a fun little adventure! The house manual and guides were super helpful, with clear instructions that made everything easy to figure out. Overall, it was a peaceful, fun, and memorable stay. I’d absolutely come back again. Highly recommend!

I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

Jorge has a great spot for you and is one of the nicest people you will ever meet … 100% recommend!!

We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)

Thanks for your hospitality. If we have work again in the area we will be back. Evelyn handled issues very well.

Oxford is my favorite place to visit on the Eastern shore and I love staying in this little place near the town park. it's so peaceful and close to everything. I love connecting with the locals I've met on my travels. I look forward to returning!

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!

I had an amazing stay at Jen’s apartment! The space was exactly as described—clean, stylish, and super comfortable. The bed was cozy, the kitchen had everything we needed, and the little touches (like the kid’s Conner and lots of board games ) really made a difference. The location was perfect—close to everything but still peaceful at night. Communication with the host was smooth and fast, and they were incredibly helpful with local tips. I’d absolutely stay here again and highly recommend it to anyone visiting beautiful Cambridge!

What a perfect weekend get away. The place was perfect. Extremely comfortable beds, lots of pillows and two deck areas outside. We cooked outside 2 nights - and loved seeing the bay from the deck. We used the nearby tennis and basketball courts, and spent the days visiting wineries and neighboring towns, and driving through the countryside. Groceries and restaurants require some planning and some driving. Loved our stay!

Condo was in a perfect location in North Beach area. Loved walking boardwalk and walked 5+ miles daily. Felt very safe in the area, everyone was so friendly. Mexican restaurant and Baia were fantastic. Very peaceful. Condo definitely worth the money. Host was very responsive and let us check in early and was quick to reply to any text questions. Loved the view!