Family-friendly holiday rentals in Southern Maryland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Southern Maryland
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southern Maryland family-friendly rentals
Family-friendly home rentals with a hot tub
Bungalow in Deale
4.86 out of 5 average rating, 361 reviewsCozy waterfront getaway on the Bay
Home in Montross
4.95 out of 5 average rating, 221 reviewsStunning Lake House Retreat on the Potomac River
Home in Kent Narrows
5.0 out of 5 average rating, 281 reviewsChester Riverfront At Kent Narrows
Home in Deale
4.98 out of 5 average rating, 115 reviewsChesapeake Waterfront Kayaks-Fish & Crabbing
Home in Arlington
4.86 out of 5 average rating, 271 reviewsArlington farmhouse w/easy access to everything DC
Home in Harwood
4.94 out of 5 average rating, 119 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Home in Edgewater
4.76 out of 5 average rating, 273 reviewsEdgewater/Mayo Getaway!
Family- and pet-friendly home rentals
Home in Montross
4.84 out of 5 average rating, 131 reviewsPotomac Waterfront Home and Estate
Guest suite in Woodbridge
4.9 out of 5 average rating, 261 reviewsT&T’s Comfy, Spacious Artists’ Retreat BnB
Cottage in Colonial Beach
4.94 out of 5 average rating, 157 reviewsBayside Cottage- In the Town with views
Home in Lancaster
4.99 out of 5 average rating, 214 reviewsRivah View
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
Guest house in Ashland
4.96 out of 5 average rating, 474 reviews2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi
Flat in Edgewater
4.92 out of 5 average rating, 409 reviewsPet Friendly Garden Apartment Near Annapolis
Flat in Washington
4.99 out of 5 average rating, 159 reviewsCapitol Hill comfy 1BR basement apt - Free parking
Family-friendly home rentals with a pool
Guest house in Glen Allen
4.84 out of 5 average rating, 478 reviewsPrivate and Quiet Pool House Convenient Location
Home in Saint Michaels
4.97 out of 5 average rating, 240 reviewsMiles Aweigh
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Apartment in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Guest house in Colonial Beach
4.96 out of 5 average rating, 50 reviewsBeach Carriage House with Pool and Cabana
Cottage in Neavitt
4.89 out of 5 average rating, 18 reviewsGrandview Cottage #2 -A special peaceful place!
Home in Woolford
4.98 out of 5 average rating, 55 reviewsGorgeous Waterfront-Beach, Pool, Pets- 7 Bd /5ba
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Richmond Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals United States
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