Family-friendly holiday rentals in Saint Leonard

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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 favourite

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

Townhouse in Del Ray

4.77 out of 5 average rating, 220 reviews

3BR/2.5BA DelRay Home near DCA & Everything (312)

Very Spacious Modern & Comfortable Home in the lovely DelRay community in Alexandria, which recently ranked as the best tourist town in the US. Close to all the top places to see and be in the DC Metro Area. The Potomac Yard Metro stop is less than 1/4 mile, Reagan-DCA airport is 1 mile, the White House is 5 miles and old town Alexandria is just 2 miles. A Target, Giant, Best Buy and chain restaurants across the street and trendy fun restaurants 10 minute walk. We look forward to hosting you!

Guest favourite

Home in Hague

4.97 out of 5 average rating, 158 reviews

Osprey's roost: Spring and summer 2025

Hidden treasure! Come join the osprey along the Potomac River in the Northern Neck of Virginia! This 4 bedroom/3 bath custom home is at the end of a quiet lane and sits on a point of land between the Potomac River and Blackbeard’s Pond, making for magnificent river views from sunrise to sunset. Enjoy swimming, canoeing, Bocce on the lawn, barbecue on the deck! Osprey’s Roost is the perfect retreat to rest and recharge, ideal for a romantic week away, a girls’ weekend or a family gathering!

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.

Superhost

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

Superhost

Home in Arlington

4.78 out of 5 average rating, 275 reviews

Lovely house! Mins to DC, airport, food, metro+

3 bedrooms (3 queen beds & 1 twin bunk beds; sleeps 8). New beds & furniture! Super convenient, spacious, clean, cozy & quiet home that is fully equipped. Free parking on street right in front of house. Full kitchen. 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; 7 min drive to DC. Super safe neighborhood; central location to Arlington & Washington

Guest favourite

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.

Superhost

Home in Tall Timbers

4.89 out of 5 average rating, 117 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Immaculate cottage with old world detail and large stone patio. Easement to water to 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. 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 favourite

Apartment in Capitol Hill

4.79 out of 5 average rating, 156 reviews

Cap Hill Private Retreat Charm, Comfort | Sleeps 4

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!

Guest favourite

Apartment in Cambridge

4.98 out of 5 average rating, 202 reviews

Private apt above garage w/ pier and water access

New 2 Bedroom apartment along the picturesque Choptank River. This quiet and spacious 2nd floor Private garage apartment features an open concept with 2 bedrooms, a full kitchen, living room, washer & dryer with optional garage area to store bikes or beach gear. Bike, walk or drive to local restaurants, parks and downtown attractions. Private beach and pier access!!! Close to all of the Ironman festivities and conveniently located to Rt 50. Kayaks on site.

Guest favourite

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 favourite

Apartment in Deale

4.91 out of 5 average rating, 619 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.