Kid-friendly vacation rentals in Saint Leonard

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Top-rated kid-friendly rentals in Saint Leonard

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

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Guest favorite

A cozy living area is highlighted by a gray sectional sofa and patterned area rug. A stone fireplace adds warmth, while a large flat-screen TV is visible. Natural light streams through windows, and a staircase leads to the upper levels. Nautical decor enhances the beach-inspired atmosphere.

Cottage in Colonial Beach

4.84 out of 5 average rating, 164 reviews

SUPERB BEACH COTTAGE- Waterview, firepit, porch!

Dig your toes into the sand at Colonial Beach when you stay the 'Hummingbird Harbour,' a 3-bed, 2.5-bath cottage along the Potomac River! Ideally located only minutes from the shore, this quaint vacation rental is the perfect family getaway, complete with an expansive backyard, fire pit, and outdoor dining area. Take in the fresh ocean air from the screened porch with a steamy cup of joe in hand, or explore the shoreline with a walk down to Dockside Restaurant & Tiki Bar, found just steps away!

Superhost

A modern kitchen features white cabinetry, a stainless steel refrigerator, and a sleek granite countertop. A stove and microwave are included, while a small dining area with two chairs is set near the window, providing natural light.

Guest suite in Logan Circle

4.72 out of 5 average rating, 130 reviews

Prime Location Studio In-Law Suite

Incredible location!!! Sitting at the heart of the bustling Shaw neighborhood, this row home in-law suite is central to everything the city has to offer! Wander into the neighboring Blagden Alley and fall into a system of alleyways booming with craft cocktails, coffee, street art, and award-winning restaurants all hosted in beautifully preserved historic buildings. Steps from the Convention Center and Metro. Professionally cleaned and is equipped with anything you may need to feel more at home.

Top guest favorite

A dining area is presented with a modern table surrounded by white chairs, offering a casual atmosphere. Natural light pours in through large windows. A beach-themed artwork depicting a tropical scene enhances the setting, while a coffee bar is conveniently located nearby.

Cottage in North Beach

4.98 out of 5 average rating, 149 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Guest favorite

A charming white cottage presents a welcoming facade, featuring a covered porch with two light blue chairs and a small table. A well-maintained lawn with green grass and a landscaped border is visible, while a white picket fence enhances the front yard.

Cottage in North Beach

4.94 out of 5 average rating, 159 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Guest favorite

A modern two-story house features multiple large windows and balconies, allowing for ample natural light. The deck showcases orange lounge chairs positioned for outdoor relaxation, while the well-maintained lawn is bordered by trees displaying autumn colors.

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Superhost

The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.

Home in Montross

4.88 out of 5 average rating, 233 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million+ old shark teeth, and a fossil cliff beach. Fishing! Hot tub on the patio! Bald eagle sightings! Theater Room!

Guest favorite

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

Home in Cambridge

4.94 out of 5 average rating, 135 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Top guest favorite

The exterior of a renovated beach house is depicted, featuring a wide entrance with steps leading to a spacious deck. The deck is furnished with a dining set and a shaded lounge area, while greenery surrounds the property, enhancing its tranquil setting.

Home in Lusby

5 out of 5 average rating, 179 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Top guest favorite

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

5 out of 5 average rating, 103 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

Four white Adirondack chairs are arranged on a grassy area, facing the tranquil waterfront. A wooden pier extends into the calm river, surrounded by lush greenery and a single tree providing shade. The clear blue sky complements the serene setting.

Home in Cambridge

4.98 out of 5 average rating, 127 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Guest favorite

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

4.93 out of 5 average rating, 169 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.

Top guest favorite

The entrance of a historic home is highlighted by a black front door with decorative hardware. A set of brick steps leads to the door, flanked by two large planters. A mature tree provides shade, while the surrounding area features a paved pathway and lush greenery.

Townhouse in Old Town

5 out of 5 average rating, 185 reviews

Heart of Old Town Alexandria|Historic|1800ft²

• Historic, Old Town Alexandria home, built in 1880 • Half a block off of King Street - Old Town's main thoroughfare • Walk Score 98 • Best of both worlds: historic home updated with all the latest amenities • Hundreds of Old Town shops and restaurants • High-speed wifi in every room • Five smart TVs, all hardwired to internet.