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Family-friendly vacation rentals in Calvert County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Calvert County family-friendly rentals

Family-friendly home rentals with a hot tub

A cozy bedroom features a spacious bed with a quilted coverlet and decorative pillows. A bedside table with a modern lamp sits beside the bed, while a mirrored dresser adds functionality. Soft, neutral tones create a calm environment, enhancing relaxation.
Guest suite in Adelphi
4.84 out of 5 average rating, 208 reviews

Cozy Suite with Hot Tub and Pool

SusannaRating, 5 stars2 months ago
Eric is an amazing host and person! Super friendly when it came to using the amenities and made us feel at home. Has great recommendations for food and local attractions. Beautiful property to walk around or just sit outside! Overall a 10/10 experience while staying at Eric’s home, couldn’t have asked for a better host for our weekend!
A charming brick house is framed by mature trees and a well-maintained front yard. A white picket fence encloses the garden, which features green grass and established landscaping. Sunlight dapples the ground, casting gentle shadows in a serene outdoor setting.
Home in Cambridge
5 out of 5 average rating, 10 reviews

Steps from Ironman MD Start

SeanRating, 5 stars21 months ago
Fantastic house in a great location. The surrounding park is beautiful and the location is incredibly peaceful. The house was great and met our needs perfectly. Two beds and a pull out sofa. Living room and kitchen has everything you’d need. Check in and out was as simple as possible. Enjoyed staying here!
Guest favorite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis
4.86 out of 5 average rating, 107 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

JohnRating, 5 stars1 month ago
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.
A serene outdoor area features a refreshing swimming pool surrounded by a spacious patio. Metal lounge chairs and tables are arranged neatly, providing comfortable seating. Lush trees and greenery offer privacy, enhancing the inviting atmosphere of the outdoor space.
Home in Davidsonville
4.95 out of 5 average rating, 19 reviews

Annapolis Elegant 5* House -3 Bedrooms Sleeps 6

CharlesRating, 5 stars22 months ago
Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.
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, 174 reviews

Celebrate Summer by Your Private Pool

JennaRating, 5 stars9 months ago
Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.
Bungalow in Deale
4.85 out of 5 average rating, 393 reviews

Cozy waterfront getaway on the Bay

MichaelRating, 5 stars1 month ago
This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.
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!
Superhost
A relaxing outdoor space features a hot tub on a wooden deck surrounded by lush greenery. Two chairs and a small table are positioned nearby, with decorative plants and a grill enhancing the inviting atmosphere.
Home in Edgewater
4.76 out of 5 average rating, 293 reviews

Edgewater/May Getaway!

JephteRating, 5 stars5 days ago
Great place to stay with family and friends. Very quiet area and a lot of parking available. Instructions was easy to follow in and out. We recommend this place for others.

Family- and pet-friendly home rentals

Guest favorite
A classic historic cottage features white siding and a steeply pitched roof. An American flag hangs from the front door, which is framed by a small porch and decorative elements. Lush greenery and a white picket fence enhance the welcoming facade.
Home in Saint Michaels
4.86 out of 5 average rating, 125 reviews

Premier St Michaels Cottage- In Town Location

Marissa & ChrisRating, 5 stars3 weeks ago
Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!
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 stars2 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!
Guest favorite
The exterior of a single-story cottage is framed by lush greenery and mature trees. A white picket fence encloses the front yard, which features a small lawn and a decorative tree. Gravel pathways lead to the front entrance, with a shaded area beside the house.
Cottage in Deale
4.9 out of 5 average rating, 166 reviews

Rockhold Creek Cottage

ShamsRating, 5 stars2 months ago
We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.
Top guest favorite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park
4.97 out of 5 average rating, 568 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars1 week ago
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
Superhost
A welcoming living area features a tan leather sofa adorned with patterned pillows. Two wooden coffee tables are centered on a textured area rug. Bright natural light streams in through a nearby doorway, while a green potted plant adds a touch of liveliness to the space.
Home in College Park
4.84 out of 5 average rating, 183 reviews

Spacious relaxing home by DC, CP, woods & lake

SusanRating, 5 stars2 weeks ago
We've stayed at Kopal's quite a few times - very peaceful neighborhood, very close to Lake Artemisia, which is lovely for walking, also very close to College Park. Great location. The house is always very clean, well-equipped and Kopal is so responsive.
Superhost
Four individuals walk together along a grassy path lined by tall trees. The warm sunlight filters through the branches, highlighting the natural scenery. A glimpse of water and a dock can be seen slightly in the background, adding to the serene ambiance.
Home in Tall Timbers
4.89 out of 5 average rating, 123 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

RobinRating, 5 stars4 days ago
Cute place in a small community of vacation homes. They don't call the area Tall Timbers for nothing. I like the corner market up the road, the restaurant and bar are old school, friendly, and lively - packed with locals.
Guest favorite
A serene waterfront scene is captured just before twilight, showcasing calm waters reflecting the soft colors of the sky. Distant lights from nearby docks create a gentle glow, framed by the silhouettes of trees and the peaceful harbor setting.
Apartment in Annapolis
4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

ThomasRating, 5 stars8 months ago
Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.
Guest favorite
A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.
Home in Saint Leonard
4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

cherylRating, 5 stars8 months ago
Our stay was great. The house is located in a quiet friendly neighborhood. The views are amazing. The house is very comfortable and so relaxing. Loved that three bedrooms each had a bathroom. The hosts were wonderful and very responsive.

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 two-story waterfront home is showcased, featuring a spacious deck and a heated pool. Lush greenery lines the gravel pathway, and well-maintained landscaping surrounds the property. Clear blue skies reflect a serene atmosphere, while the water glimmers nearby, enhancing the tranquil setting.
Home in Lottsburg
4.96 out of 5 average rating, 69 reviews

Heron Harbor

DianaRating, 5 stars34 months ago
All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!
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 stars3 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
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.
Home in Sherwood
4.92 out of 5 average rating, 12 reviews

Private Retreat with BIG Water Views!

JillRating, 5 stars59 months ago
This lovely house sits on a private lot with spectacular water views. The pool is pristine and was a perfect depth for both the children and the adults. in our group. There were 10 of us (three generations) and we had plenty of room to feel comfortable.
Guest favorite
A comfortable living space features a brown leather sofa and elegant dining table. A decorative sailboat is displayed on a sideboard, with light streaming through window blinds. Potted plants add a touch of greenery to the area, enhancing the inviting ambiance.
Condo in Annapolis
4.89 out of 5 average rating, 62 reviews

GREAT LOCATION ON SPA CREEK

LauraRating, 5 stars9 months ago
We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.
Guest favorite
A hot tub is positioned in the foreground, with bubbles gently rising. A clear swimming pool extends beyond, surrounded by various seating options, including lounge chairs and shaded areas. Lush greenery creates a serene backdrop, enhancing the relaxation space.
Apartment in Colonial Beach
4.98 out of 5 average rating, 47 reviews

Bluebird's Nest

CarolineRating, 5 stars3 weeks ago
we stayed as a family of four, two adults, two children. Edwards place was gorgeous, clean, and felt bigger than in the pictures! My favourite spots were the little balcony from which you could see the water and the stars, and the STUNNING garden with beautiful pool and hot tub. The beds were so comfortable, and the pillows were perfect. There was tons of storage available in the bedrooms. The kitchen was so well appointed, and had every tool and gadget you could likely need! We walked to the Dockside tiki bar, and a short drive to all other spots. We also loved walking to the beach nearby. Edward was a great communicator, and answered any questions very quickly, and was proactive in sending information about getting into the property, using the pool etc. A true 5 star spot!
The inviting living room features a large gray sofa with a white throw and two patterned blue chairs. A glass coffee table is centered on a decorative rug, while a wall-mounted fan provides airflow. A landscape photograph adorns the wall, adding visual interest.
Cottage in Neavitt
4.78 out of 5 average rating, 23 reviews

Grandview Cottage #2 -A special peaceful place!

RobertRating, 5 stars1 week ago
The cottage was the perfect serene retreat. The kitchen was well stocked so that we did not need to go to a restaurant for many meals. We especially enjoyed sitting on the dock to read while taking in the gorgeous view. We also brought our own kayak and took advantage of the boat house where we could store the boat overnight. Ann was a fantastic and responsive host! We will be back!

Destinations to explore