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Family-friendly vacation rentals in Southern Maryland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Southern Maryland family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Two white Adirondack chairs are positioned on a wooden deck, facing a serene view of a water body and green landscape. A saltwater pool is visible in the foreground, surrounded by a protective fence, while trees frame the backdrop.
Home in Lancaster
4.67 out of 5 average rating, 21 reviews

Great Family Vacay! Dock, pool, fire pit, hot tub

KateRating, 5 stars1 month ago
Our family and friends had a lovely time in Cynthia's home. The setting is very pretty, the dock was a great place to fish and crab from and the beach offers another great hangout spot. The added bonus is that her home is just a 10-minute walk to a cute little restaurant in a marina with great oysters and cocktails.
Superhost
A modern living space is depicted, featuring a sleek dining table with comfortable chairs and a well-equipped kitchen in the background. Natural light enters through large windows, illuminating the neutral-toned decor. A cozy seating area includes a stylish sofa that complements the room's aesthetic.
Apartment in Washington
3.67 out of 5 average rating, 3 reviews

Washington 2 Bedroom Apt Near U.S. Capitol.

ChadRating, 5 stars110 months ago
This was a very great find. Affordable for the part of the city we were in. Lots of energy and activity around the area, with plenty of places to eat/drink within a few block radius. Close to everything you need to be close to downtown. Easy check-in process. Beautiful, clean apartment. All in all, a wonderful spot to stay.
Guest favorite
A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.
Apartment in Arnold
4.96 out of 5 average rating, 175 reviews

Celebrate Summer by Your Private Pool

SaraRating, 5 stars3 days ago
We had a wonderful stay at Brenda’s place! The pool is amazing and the whole outdoor area is great. With the grill, chairs and tables, outdoor fire (two of them!) we had such a great weekend escape. Very quiet area, we didn’t see the hosts the whole time which made it feel private. They were so responsive and helpful all weekend. Wonderful stay and we will definitely be back!
Top guest favorite
An aerial view captures the expansive waterfront estate surrounded by lush greenery and a tranquil waterway. The pier extends towards the water, while the house is set back from the banks. Nearby structures include docks and quaint homes along the shoreline.
Home in Deale
4.99 out of 5 average rating, 146 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

LauraRating, 5 stars1 week ago
Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!
Superhost
The exterior of Club Wyndham National Harbor is displayed, showcasing a multi-story building with a warm palette. A swimming pool is visible at the forefront, framed by lounge chairs. An American flag is prominently featured, indicating proximity to the Gaylord Convention Center.
Condo in National Harbor
4.78 out of 5 average rating, 32 reviews

Wyndham National Harbor ツ 3 Bedroom Deluxe!

RebeccaRating, 5 stars4 months ago
Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.
Two kayaks are positioned on a grassy area by the water, reflecting a sunset sky filled with warm hues. A wooden pier extends into the lake, framed by bare trees, offering a serene view of the calm water surface.
Bungalow in Deale
4.85 out of 5 average rating, 394 reviews

Cozy waterfront getaway on the Bay

BillRating, 5 stars3 days ago
The ultimate Maryland water experience. Beautiful house with perfect amenities to enjoy the bay. With the dock, the view, the crabbing, the fishing, and the kayaking, you save time and money by having everything at your fingertips. The hot tub was wonderful even in summer. The house has everything you could want for a relaxing stay. We ate the crabs we caught every night for a week! Plenty to do and see in the area, too. Definitely want to return!
Guest favorite
A modern multi-story building with a distinctive architectural design is showcased. The exterior features a blend of light-colored stone and large windows, providing a contemporary look. Balconies can be seen on multiple floors, enhancing the appeal of the structure.
Condo in National Harbor
5 out of 5 average rating, 19 reviews

Wyndham National Harbor- 3 bedroom

PriscillaRating, 5 stars2 weeks ago
Brooke was very helpful in our booking and gave great suggestions. The place at National Harbor was exceptional and from the check in to the check out, the staff were extremely helpful and went above & beyond. We had a great rental that exceeded our expectations.
Guest favorite
The front of a charming duplex features a prominent bay window and a welcoming porch adorned with a large umbrella and seating. Bright flowers line the railing, and an American flag is displayed, enhancing the inviting façade surrounded by neatly trimmed greenery.
Townhouse in Annapolis
4.83 out of 5 average rating, 128 reviews

You'll Never Want to Leave

AlexandraRating, 5 stars5 months ago
We thoroughly enjoyed our stay at Laurie's home! It was a great location and the home matched the description. We had everything we could have asked for and more, and Laurie was a great host. Would definitely stay there again!

Family- and pet-friendly home rentals

Superhost
A serene water view is presented, featuring a calm lake that reflects a cloudy sky and surrounding trees. The stillness of the water enhances the scenery, showcasing a harmonious blend of natural elements against a backdrop of soft blues and whites.
Cottage in Wittman
4.87 out of 5 average rating, 151 reviews

Perfect St. Michaels Getaway

SamRating, 5 stars2 months ago
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.
Guest favorite
A view from the studio's entrance shows a wooden fence leading to a sidewalk, bordered by greenery and colorful flowerbeds. A red vehicle is parked along the street, with a house visible in the background featuring a striped awning.
Apartment in Arlington
4.93 out of 5 average rating, 677 reviews

Studio Apt, private w/Kitchenette-10 min to Metro

BrendanRating, 5 stars2 weeks ago
Nestled in the Aurora Hills neighborhood of Arlington, you'll find a gem of a listing, far enough from the hustle and bustle of Pentagon and Crystal City but close enough to be there in mere minutes. Beyond that, this locale is close enough to the District that you can be at the Smithsonian and assorted museums in no time, and can easily access the Pier/Naval Yard with a simple transfer. As for the amenities of this location, it has everything you'd need for a short to moderate stay. The shower was incredibly hot, which I preferred. So, if you are looking for a place a bit out of the mix but close enough to be in it at a moment's notice, then please look no further than this great listing.
Top guest favorite
A row of charming brick townhouses is presented, each with distinct colors and architectural details. A well-kept front yard features low-maintenance landscaping, with a small table set in the outdoor area. The street is lined with trees, enhancing the neighborhood's appeal.
Apartment in Washington
4.99 out of 5 average rating, 239 reviews

Capitol Hill-1BR basement apt-Free parking

EmmaRating, 5 stars3 days ago
Incredible place to stay! The hosts were flexible, responsive, and kind. Very accommodating regarding check in and check out. Would highly recommend!
Superhost
A modern studio space features a spacious bed with crisp white linens, accompanied by a turquoise dresser and a mirror. A cozy table for two is positioned next to the window, which is covered by a light grey blind. Natural light enhances the warm wooden flooring.
Guest suite in Washington
4.81 out of 5 average rating, 228 reviews

Studio at English Basement in Georgetown

DavidRating, 5 stars1 month ago
Great place to stay in Georgetown. Place was clean and felt hospitable
Superhost
The exterior of the cottage features a welcoming yellow facade, complemented by a manicured lawn with shrubs and mulch. A wooden deck with white columns provides entry to the front door, which is flanked by large windows. An American flag hangs proudly to the left.
Cottage in Colonial Beach
4.94 out of 5 average rating, 171 reviews

Bayside Cottage- In the Town with views

BradyRating, 5 stars2 days ago
My family and I greatly enjoyed our stay at the cottage. It was perfect for our family. The location was great. The cottage smelled clean upon entering and we were thrilled by the cleanliness of the entire cottage. We appreciated all the amenities provided. As we were returning to the cottage one day, Eddie stopped by to ask if everything was ok and to let him know if we needed anything. We also enjoyed getting to know the neighbors nearby as we sat on the beautiful porch with beautiful flowers and landscaping. We definitely would love to return in the near future!
Guest favorite
The exterior of a charming townhome is showcased, featuring a vibrant front garden with lush greenery and decorative plants. A set of stairs leads up to the entrance, framed by a white railing. The entrance is marked by a blue door, enhancing the inviting look of the property.
Guest suite in Washington
4.85 out of 5 average rating, 186 reviews

Musical H Street/Trinidad Basement Apt w/ parking

HallieRating, 5 stars3 weeks ago
David and Elizabeth’s place was perfect for my fiancé and our dog Kai. We attended a music festival at RFK and it was a short drive away. We actually ended up riding scooters back because it is so close by! There are so many restaraunts and things to do within walking distance. Check-in was super easy and it’s a very homey, comfortable space. The kitchen has a small fridge, toaster oven, microwave and hot plate with pots, pans, and everything you need to prepare a basic meal. We were able to set our dogs crate up (he’s a medium sized husky) perfectly and still had plenty of space to move around. Finding street parking was super easy and close by. You can hear noise from above at times for sure… ear plugs and a night time noise machine are provided to help. Overall we enjoyed our stay!
Superhost
A spacious studio room features a cushioned bed with a blue coverlet, positioned against a white wall with a framed artwork depicting a serene lake scene. A small table and chair are visible nearby, along with a mini-fridge and coffee area.
Guest suite in Washington
4.81 out of 5 average rating, 548 reviews

Cozy Guest Basement Suite w/ Private Entrance

JessieRating, 5 stars1 week ago
My friend and I loved our stay! It was a lovely little neighborhood. Alex and Shelby’s place was everything that we needed. Cute and quaint. Only the slightest of pitter patters heard from upstairs. Very clear instructions for checking in and checking out. Convenient for public transportation and provided metro cards were a great gift. Would highly recommend to anyone looking for a place to stay in the DC area!
Top guest favorite
An outdoor patio area features a picnic table and a fire pit, surrounded by comfortable seating under a large umbrella. The sunroom with large windows provides views of the river. Nearby, a grill is present for outdoor cooking.
Home in Lancaster
4.99 out of 5 average rating, 234 reviews

Rivah View

PeteRating, 5 stars2 months ago
Relaxing, well-kept property and house with a view. Plenty of good food in next town over. If you haven't been to Northern Neck, stay here and enjoy some peace and quiet.

Family-friendly home rentals with a pool

Guest favorite
An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.
Cabin in Saint Michaels
4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KateRating, 5 stars2 weeks ago
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.
Superhost
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars1 month ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Guest favorite
The front bedroom features a queen bed adorned with floral-patterned linens. Two nightstands with vibrant orange lamps flank the bed. A wall art piece depicting a cyclist stands above the headboard, while an exposed brick fireplace is visible on one side.
Townhouse in Washington
4.93 out of 5 average rating, 409 reviews

Dupont West 1: Charming 2BR

StephanieRating, 5 stars2 days ago
Our stay was fantastic! The location was SO close to everything and the walkability to some great restaurants was great! Greg was very informative and responsive and I def recommend taking advantage of the parking offered, well worth it in this busy neighborhood. This was the cleanest Airbnb I have ever stayed in, everything was well labled and the kitchen had everything you need to cook! The home and the the neighborhood were very charming and if you like unique stays, I'd def recommend checking it out! We would stay here again in a heartbeat!
Superhost
A modern kitchen is visible, featuring stainless steel appliances and sleek cabinetry. A cozy living area showcases a curved sofa set atop a plush red rug, with two round coffee tables. Light enters through windows, creating a bright and inviting space.
Apartment in Washington
4.79 out of 5 average rating, 433 reviews

#2 Foggy Bottom/Georgetown Apartment

KellyRating, 5 stars1 month ago
We had a great time and parked right in front of the apartment. After I stood there and held the spot for our big truck. Lol took my hubby an hour to get back to me but I remained standing for him to park and not letting anyone else park there 🤣🤣🤣🤣 place was great. Thanks!
Top guest favorite
An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.
Place to stay in Annapolis
4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

PaulRating, 5 stars1 month ago
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.
Top guest favorite
A cozy living area features large bay windows providing ample natural light. A sectional sofa and patterned rug add comfort, while a modern coffee table sits in the center. A flat-screen TV and entertainment unit complete the space, enhancing its inviting design.
Townhouse in Washington
5 out of 5 average rating, 109 reviews

Charming 3BR Rowhouse in Shaw/Bloomingdale

ThanyRating, 5 stars2 months ago
Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!
Superhost
A modern pool area is surrounded by lounge chairs arranged neatly around the water. Private cabanas with navy blue canopies are positioned on one side, offering shaded seating. Lush greenery and tall buildings are featured in the background, creating an inviting outdoor space.
Apartment in Tysons
4.83 out of 5 average rating, 148 reviews

Tysons luxury high-rise Apartment near metro

KatrinaRating, 5 stars41 months ago
Very responsive host. Clean space in a great location!
Guest favorite
A private pool is surrounded by a fenced patio, featuring a concrete deck. The clear blue water reflects the surrounding trees, while the guest house is visible in the background. A railing leads into the pool, providing easy access.
Guesthouse in Glen Allen
4.84 out of 5 average rating, 565 reviews

Private and Quiet Pool House Convenient Location

MicheleRating, 5 stars2 days ago
We really enjoyed our stay. The pool alone was 5stars and the cleanliness and guest house was exceptionally nice as well. My grandson claimed to have "The BEST day ever" swimming in the pool. we loved the privacy and the beautiful flowers and landscaping it was perfect. I hope to be able to come back soon.

Destinations to explore