Kid-friendly vacation rentals in Southern Maryland

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Southern Maryland

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A grassy yard is shown with play equipment, including a blue and yellow swing set with multiple swings and a slide. Trees provide shade in the background, while nearby outdoor structures are visible.

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

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.

Guest favorite

A playset is situated in a grassy backyard, featuring swings, a climbing wall, a slide, and monkey bars. The wooden structure has a roof and various play features, surrounded by trees and a wooden fence for privacy.

Apartment in Vienna

4.92 out of 5 average rating, 103 reviews

Flint Hill Bright and Spacious Basement Apt, WiFi

This spacious and light-filled unit is perfect for touring Washington, DC with the whole family. It is the lower level, with separate entry, of a large family home. 25-30 minutes to downtown driving or by Metro. We are a short car/cab ride to the Vienna metro station. Many beds, a kitchenette, laundry machines, and a playset in the backyard for the littles. Street parking is by permit for up to one car. Put your feet up after trekking around; we’ve got board games and complimentary popcorn.

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, 232 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, 133 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.

Guest favorite

A public park is depicted with natural elements including rocks and trees. Soft rubber flooring is visible, providing a safe play area. The background features structures, indicating a developed area, with cloudy skies enhancing the tranquil setting.

Apartment in Fredericksburg

4.95 out of 5 average rating, 164 reviews

Historic Apartment, centrally located DnTwnFXBG!

Immerse yourself in the charm of Fredericksburg's historic district with this captivating 1st-floor apartment with nearly 500 sqft, a group of up to 4 will sleep comfortably. Boasting a modern-boho style, this delightful space offers a large bedroom, full bathroom, & a fully-equipped kitchen that opens up to a spacious living and dining area. A large screen TV in the living space provides indoor entertainment after a night out! This is #1 of 3 of our apartment listings in the building!

Superhost

An aerial view of a colonial-style home with a brick exterior and multiple gabled roofs is presented. The property is surrounded by neatly trimmed hedges, and a spacious lawn leads towards a serene lakeside backdrop, visible through trees. A vehicle is parked in the driveway.

Guest suite in Warrenton

4.93 out of 5 average rating, 121 reviews

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

Guest favorite

An outdoor play area is visible, featuring wooden structures including a swing set, a climbing feature, and a balance beam. Lush greenery surrounds the area, creating a natural setting. Soft grass and bark pathways are present, enhancing accessibility for children.

Guesthouse in Annapolis

4.9 out of 5 average rating, 103 reviews

Private Cottage on gated estate

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper. Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

Top guest favorite

A well-manicured lawn leads to a serene waterfront, framed by trees. A pool lies in the foreground, accompanied by a large umbrella providing shade over cushioned lounge chairs. A fire pit with seating is visible in the distance by the water.

Cottage in Easton

5 out of 5 average rating, 102 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

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.

Guest favorite

A spacious living area features warm wooden flooring and coffered ceilings. A dining table with four chairs is visible, while a stylish staircase leads to the upper level. Natural light illuminates the space from nearby windows, creating a welcoming atmosphere.

Townhouse in Washington

4.92 out of 5 average rating, 154 reviews

Spacious Family Retreat in Tranquil Neighborhood

Our home is one of the largest homes in the neighborhood. It is beautifully decorated for your enjoyment. Our large family room will make you feel like you are at home. House is 2,700 sq ft. The house is a close 2.5 miles from the well-known National Zoo. Also, 0.7 miles to the METRO station that has a direct route to the National Mall - a perfect tourist destination.

Top guest favorite

A spacious recreation area features a table tennis setup positioned on polished wooden flooring. Large glass doors provide access to outdoor views of surrounding greenery, enhancing the natural light within the space. Additional seating and equipment are visible along the walls.

Home in Annapolis

4.98 out of 5 average rating, 168 reviews

Quiet Waterfront

Waterfront guesthouse in gated community on a creek off of the Severn River with clubhouse, swimming beach, tennis court. Approximately five miles from downtown Annapolis. NO PETS, NO SMOKING, NO PARTIES. Parking for up to four cars only. Anne Arundel County License Number STR-120.