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Kid-friendly holiday rentals in Saint Leonard

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Saint Leonard family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Hague
4.97 out of 5 average rating, 162 reviews

Osprey's roost: Spring and summer 2025

DavidRating, 5 stars1 week ago
Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.
Guest favourite
Home in Saint Leonard
4.95 out of 5 average rating, 58 reviews

Block to beach! Relax, enjoy views & game room.

MeganRating, 5 stars5 months ago
This is a lovely and friendly home - which is no surprise as it matches my impression of the owners! My family created a spontaneous plan to visit this area and Terri & Bo accommodated us very graciously despite the short notice. Their home is lovely, well-equipped and designed for family fun. It is convenient to all the wonderful activities in the area, in particular the fossil hunting, which was the draw for our crew. Although we found fossil's on our own, Terri's information directed us to a guide who was extremely knowledgable and added a great deal to our experience. I would highly recommend this home for a getaway at any time of year. The area is well-known as a summer destination, but we visited over New Year's and loved exploring the beautiful beaches in the off-season.
Superhost
Home in Saint Leonard
4.75 out of 5 average rating, 12 reviews

Waterfront! The River's Roost on the Patuxent!

AlexandrosRating, 5 stars4 months ago
My wife, 4 year old son and I enjoyed a week at John’s beautiful home on the Patuxent River. The house and property were perfect and the views were amazing every day. The house had everything we needed and we felt right at home. He was very responsive and helpful when we had questions. We look forward to staying here again in the summer!
Top guest favourite
Home in Port Republic
5 out of 5 average rating, 38 reviews

Coastal Haven- Beach w/ BBQ

KarenRating, 5 stars1 month ago
My family had a wonderful stay at this BNB. Lots of space for everyone. Big rooms, really nice kitchen. It was very neat and clean. The neighborhood access to the beach was a plus. The neighborhood is very nice and convenient to the highway.
Top guest favourite
Home in Shady Side
5 out of 5 average rating, 171 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

TyRating, 5 stars3 days ago
Chose this spot for our honeymoon and it was fantastic. You’ll love the views and infinite amenities but most of all, Evan is an incomparable host. I’d book with him again, no doubt. He’s clearly gone above and beyond to make sure guests feel at home (if your home is impeccably decorated and designed for ultimate comfort). He’s gone to great lengths to make sure his guests have a memorable experience and it’s appreciated!
Top guest favourite
Home in Leonardtown
5 out of 5 average rating, 117 reviews

White Point Cottage -- Quiet Waterfront Getaway

MichelleRating, 5 stars1 month ago
SUCH wonderful friendly, and personable host!! We love Victor ;-). We (3 ladies) intentionally had a “relax our brain” peaceful weekend. There is so much to write. We enjoyed the peaceful, relaxing and comfortable stay. The decor is delightful; so welcoming! We loved the personal touches like the welcome note and fresh cut flowers. There were beautiful indoor real plants and amazing views from every angel! They also recommended local places to go. We enjoyed siping coffee in the sun room, giggling all night drinking wine and sunset views. Thank you for proving the best quiet place we could ask for. Our stay exceeded our expectations. We appreciate the details and your attentiveness!
Guest favourite
Home in Port Republic
4.95 out of 5 average rating, 19 reviews

Sea&Sails

AnnetteRating, 5 stars4 weeks ago
The house was perfect. Clean, bright, modern and walkable to the shoreline. We can’t wait to go back!
Guest favourite
Home in Saint Leonard
4.85 out of 5 average rating, 48 reviews

Waterfront house with private beach and pier

GilRating, 5 stars2 months ago
We had a great stay on the water at Shuran’s place. Charming house with a beautiful view, very peaceful and quiet. The house was well stocked, with everything you would need, including in the kitchen. Very nice outdoor area with plenty of opportunities to fish, go kayaking, or just relax next to the water. Highly recommend and would definitely stay again.

Family-friendly apartment rentals

Guest favourite
Flat in Upper Marlboro
4.95 out of 5 average rating, 135 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

HalleRating, 5 stars4 days ago
It was a great and very calm place to stay!
Top guest favourite
Flat in California
4.92 out of 5 average rating, 216 reviews

Our Little Piece of Heaven

TinaRating, 5 stars1 week ago
We went to Southern Maryland to celebrate our 44th Wedding Anniversary as it was where we met back in high school. We were greeted at Tom & Michele’s place with a sweet chalkboard message, flowers and a nice little cake to help us feel special and celebrated. That was very kind. Their apartment is extremely clean and very comfortable. The backyard is absolutely beautiful and very relaxing. We didn’t need help with navigating the area as we grew up there so we spent most of our time visiting places from our youth. Tom & Michele reached out to us during our visit to make sure we were doing okay. We are quiet people and don’t require a lot of assistance so it was nice to be asked but we were good. For us it was nice to have a chance to spend quiet time alone together and Tom & Michele gave us that. Should we find ourselves back in Southern MD we would definitely stay there again. Thank you for a wonderful visit ♥️
Top guest favourite
Flat in Leonardtown
4.98 out of 5 average rating, 136 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

AngRating, 5 stars2 days ago
Vickie and Scott were so welcoming and friendly. Respecting our privacy, yet nice conversations on our way in and out. The views, pier, and accommodations were exactly what was pictured and described. We will definitely be back. Location was only 10 minutes from downtown Leonardtown. Beautiful!
Top guest favourite
Flat in Lexington Park
4.97 out of 5 average rating, 569 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars2 weeks 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.
Guest favourite
Flat in North Beach
4.96 out of 5 average rating, 132 reviews

Bayside Oasis of Southern Maryland

KathrynRating, 5 stars4 days ago
We really enjoyed our stay at Sherril’s place. The location was peaceful and private but with easy access to the beach, boardwalk, shops, and great restaurants. The apartment was super clean and had everything we needed. Would highly recommend to anyone looking for a great introduction to the lovely town of North Beach.
Guest favourite
Flat in Capitol Hill
4.9 out of 5 average rating, 144 reviews

Studio apartment close to metro

ElliotRating, 5 stars2 weeks ago
Such a great stay and very convenient location! Directly around the corner from the Metro. Perfect for an overnight stay in the city. Very detailed instructions to make check-in/put a breeze. Will happily stay here again!
Guest favourite
Flat in Deale
4.91 out of 5 average rating, 621 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

MichelleRating, 5 stars2 months ago
We had a wonderful stay at Shawn's place. It is located in an absolutely beautiful area with a gorgeous view of the water. The place was beautifully decorated, and the bed was very comfortable. There were plenty of places to relax outside with a view of the water. We enjoyed taking the kayaks out and watching the sunset each night. Shawn was a lovely host and is a genuine person who wants you to have the best stay!
Top guest favourite
Flat in Church Creek
4.97 out of 5 average rating, 417 reviews

Church Creek Natures' Rest

ChristinaRating, 5 stars3 weeks ago
This place was so clean and comfortable. The deck was very quiet and private. The entire place was very accommodating. The beds were so comfy that it was hard to get motivated in the mornings….lol. The local Rise Up coffee was a special touch. It is one of my favorite places to get coffee when I’m in the Cambridge area. I had two other quest with me and they too agree that the place was delightful. The steps going up to the apartment were a bit difficult for my 77 year old mother but other than that we had a wonderful visit. I would highly recommend Kara’s place. Thank you again!

Family-friendly apartment rentals

Top guest favourite
Apartment in Capitol Hill
4.99 out of 5 average rating, 130 reviews

Centrally located Capitol Hill one-bedroom unit

SarahRating, 5 stars4 days ago
This might honestly be the best Airbnb experience we have ever had. Celia was a wonderful host, very proactive and made us feel right at home. We were in town for my birthday and we were welcomed with a sweet birthday treat and a card, some delicious granola, and there was chocolate on the bed! There were also some snacks including fresh fruit and granola bars as well as coffee and tea available. The location is perfect for walking around the Capitol Hill area and literally a few minutes walk away from the metro. It’s also walking distance to the Nationals stadium. I truly have no complaints about this stay, I would absolutely come again. Plus there was a sweet neighborhood cat that greeted us! Book this place!! You will not regret it.
Guest favourite
Apartment in Capitol Hill
4.97 out of 5 average rating, 101 reviews

"La Casa Bianca" 3 Bed Home by H St & Union Market

TahneeRating, 5 stars1 week ago
Hosts were very helpful and very responsive when I had questions. The place was exactly as described. We were able to walk to our destination easily. The house was very neat and clean.
Top guest favourite
Apartment in Annapolis
4.99 out of 5 average rating, 151 reviews

New Downtown Annapolis Condo With Free Parking

CheriRating, 5 stars4 days ago
Perfect location for exploring Annapolis attractions via walking including Naval Academy and downtown. A bonus for me, all areas were wheelchair accessible (except balcony). Very clean and well maintained! Bed was super comfy!
Guest favourite
Apartment in Northeast Washington
4.95 out of 5 average rating, 177 reviews

Stylish apt w free gated parking, kitchen & patio

KristenRating, 5 stars1 week ago
We had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!
Guest favourite
Apartment in Logan Circle
4.89 out of 5 average rating, 465 reviews

Bright, large zen studio on historic Logan Circle

BrookeRating, 5 stars2 weeks ago
Benjamin was a very responsive host.
Guest favourite
Apartment in Oxford
4.98 out of 5 average rating, 129 reviews

Cozy Oxford Getaway

StephanieRating, 5 stars1 week ago
Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!
Guest favourite
Apartment in Dupont Circle
4.95 out of 5 average rating, 120 reviews

Lux in heart of DC social scene, free parking!

DaphneRating, 5 stars1 month ago
very nice place and very well situated. It is clean, decorated with taste (lovely plants) and has everything you need! beds are also very comfortable. I definitely recommend!
Guest favourite
Apartment in Northwest Washington
4.93 out of 5 average rating, 211 reviews

Unique, charming garden apartment

BettinaRating, 5 stars2 weeks ago
Great apartment! Sean’s apartment is very comfortable and tastefully decorated. It is completely quiet at night and the bed is good. There is a good vibe in the neighbourhood and the apartment is less than five minutes from a Green Line metro station that will take you directly to the best art museums in the city. Sean and his co-hosts are very helpful and responsive. I hope to come back to Washington one day and if that happens, I will definitely try to book Sean’s apartment again. Thank you Sean, Megan and Loren for all your helpfulness and a lovely stay!

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