Family-friendly vacation rentals in Saint Leonard

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Saint Leonard

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Woolford

5 out of 5 average rating, 116 reviews

Starboard on McKeil Point, w/heated pool & hot tub

Starboard on McKeil Point is a beautiful 5 bedroom, 3.5 bath private waterfront home on five acres overlooking the wide water of Fishing Creek - the perfect compound for families & groups. The house features water views from every turn. Outdoor amenities include a generous screened-in porch, a private dock, a sandy beach, a heated salt water pool & a hot tub. There is also a one bedroom apartment on the second floor of the carpenter's barn which sleeps 6 and includes a full bath and kitchenette.

Superhost

Home in Arlington

4.78 out of 5 average rating, 273 reviews

Newly renovated; mins to DC, airport, food, metro

Newly renovated with brand new beds & furniture! Super convenient, spacious, clean, cozy & quiet home that is fully equipped. Free parking in driveway and free street parking. Full kitchen and accessories. A few blocks from metro (train) with easy access to downtown Washington DC and monuments, 5 mins to DCA (Reagan) airport, 5 minutes from mall, only blocks walking from shopping, restaurants, and 7 minute drive to DC. Super safe neighborhood and central location to Arlington & Washington DC.

Superhost

Home in Queenstown

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

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Home in Saint Leonard

4.9 out of 5 average rating, 129 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

Home in Lusby

4.95 out of 5 average rating, 170 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Guest favorite

Apartment in Capitol Hill

4.79 out of 5 average rating, 155 reviews

Comfortable Historic Cap Hill Private Apt/Sleeps4

This newly updated 1 bedroom apartment in my historic Capitol Hill row house, originally built in the 1880's, sleeps 4 comfortably and boasts a fully-stocked- kitchen; spacious open floor plan; in-unit washer/dryer; cable flat-screen television; full bathroom with fresh modern remodel; master bedroom with Queen bed; spacious living area with two-pull out sofas. I include a parking pass that allows you to park right out front or you're a short walk to many public transport hubs!

Superhost

Home in Tall Timbers

4.89 out of 5 average rating, 115 reviews

St Mary’s Potomac River Cottage with Sunset View

Immaculate cottage with old world detail and massive stone patio. Enjoy the fantastic Southern Maryland sunsets dipping beyond the Potomac River. Situated in St Mary’s County near Piney Point and St George’s Island we are a short walk to Tall Timbers Marina. Boats and polite Pets are welcome with prior approval. Central heat & air conditioning, Front-yard fire-pit, Fast Internet, Smart TVs, Cable 2 Plastic Kayaks Fully stocked Kitchen, and bedding Crab net Fish Table

Guest favorite

Apartment in Alexandria

4.95 out of 5 average rating, 194 reviews

Enchanted! 1BR Apt near DCA in quiet neighborhood

Full accomodations and amenneties with plenty of space. Books, Movies and Games are available for rainy days. Curl up by the fireplace on cool nights. Although the listing says "not suitable for kids 2-12" I leave that decision up to you. It is not childproof for younger children so I don't want to be responsible for your child's safety, however kids are welcome. An infant would be fine but you will have provide the bed and bedding and take care of safeguarding.

Guest favorite

Home in North Beach

4.97 out of 5 average rating, 105 reviews

Bayfront Home with Amazing Rooftop Deck!

Large, comfortable home is made for family and friends to get together (up to 15 guests). Your morning walk or jog is out the front door to the boardwalk or beach. Walk across the street for restaurants, ice cream, daily wine tastings, an organic market, yoga, spas, local art, antiques and a friendly hometown coffee shop. About an hour from DC, Baltimore & Northern Virginia, it is located 5 to 10 minutes from popular local wedding and event venues.

Guest favorite

Apartment in Deale

4.91 out of 5 average rating, 618 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Guest favorite

Cottage in Colonial Beach

4.93 out of 5 average rating, 168 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Guest favorite

Cottage in California

4.97 out of 5 average rating, 224 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.