
Family-friendly holiday rentals in Saint Michaels
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Saint Michaels
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Saint Michaels family-friendly rentals
Family-friendly home rentals with a hot tub

Steps from Ironman MD Start

Nautical Vibe Walk 2 Harbor Pubs USNA

Parkfront Hot Tub Haven for Families & Pets

Charming Annapolis Water View Home

Annapolis Elegant 5* House -3 Bedrooms Sleeps 6

Large Home with Pool & 7 bedrooms; sleeps 21

Celebrate Summer by Your Private Pool

Cozy waterfront getaway on the Bay
Family- and pet-friendly home rentals

Cottage with Modern Updates - Walk to Waterfront!

Premier St Michaels Cottage- In Town Location

Brand New Reno in Historic Dist w 2 Parking spots

Secluded acre near BWI and Baltimore

Walk to famous Tiki Bar on Solomons Island!

Carriage House near Navy Stadium, parking, pets

Historic St. Mary's City, MD

Spacious relaxing home by DC, CP, woods & lake
Family-friendly home rentals with a pool

Chestertown Watson Family Farm

Bay Breeze Retreat

Rollingside: Two-Room Guest Suite

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

Private Retreat with BIG Water Views!

Pilot House

Grandview Cottage #2 -A special peaceful place!

Piney Grove Farm
Quick stats about holiday rentals that are family-friendly in Saint Michaels
Total rentals
20 properties
Nightly prices starting at
£172 before taxes and fees
Total number of reviews
2.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Nationals Park
- The White House
- National Mall
- Betterton Beach
- Georgetown University
- District Wharf
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Patterson Park
- Georgetown Waterfront Park
- Washington Monument
- National Harbor
- Six Flags America
- National Air and Space Museum
- Crystal Beach Manor, Earleville, MD
- Smithsonian American Art Museum
- Lincoln Park
- Library of Congress
- Killens Pond State Park