Kid-friendly holiday rentals in Annapolis
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Annapolis
Guests agree: these family-friendly rentals 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 Annapolis family-friendly rentals
Kid-friendly house rentals
Home in Annapolis
4.95 out of 5 average rating, 348 reviewsNew Hotel Chic
22–29 Apr
Home in Annapolis
4.94 out of 5 average rating, 287 reviewsCozy 2br home w/ parking in downtown Annapolis
11–18 Jan
Home in Shady Side
5.0 out of 5 average rating, 116 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
11–18 Jan
Home in Annapolis
4.95 out of 5 average rating, 103 reviewsThe Navy House-Walk or Shuttle Downtown! 3 bd
5–12 Aug
Home in Annapolis
4.99 out of 5 average rating, 145 reviewsCharming house; walk to everywhere in Annapolis
3–10 Nov
Home in Annapolis
4.98 out of 5 average rating, 129 reviewsCrab Cakes and Football Historic District
27 Oct – 3 Nov
Home in Annapolis
4.95 out of 5 average rating, 146 reviewsSophisticated & Spacious Historic Home w/ Parking!
17–24 Nov
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
7–14 Nov
Family-friendly apartment rentals
Flat in Edgewater
4.92 out of 5 average rating, 399 reviewsPet Friendly Garden Apartment Near Annapolis
1–8 Jul
Flat in Sykesville
4.97 out of 5 average rating, 279 reviewsIn the Heart of Sykesville! 2 Bedroom Suite
13–20 Dec
Flat in Bethesda
4.99 out of 5 average rating, 244 reviewsImmaculate Apartment in Downtown Bethesda
4–11 Feb
Flat in North Beach
4.97 out of 5 average rating, 102 reviewsBayside Oasis of Southern Maryland
2–9 Nov
Flat in Sykesville
4.82 out of 5 average rating, 342 reviewsQuiet Studio Basement Apartment
21–28 Jul
Flat in Sykesville
4.96 out of 5 average rating, 130 reviewsHickory Haven •1B King •Bsmt Apt •Clean •LG
26 Jul – 2 Aug
Flat in Stevensville
4.97 out of 5 average rating, 239 reviewsBoutique by the Bay
19–26 Jan
Flat in Essex
4.97 out of 5 average rating, 223 reviewsA place unique on sue creek
18–25 Nov
Family-friendly apartment rentals
Apartment in Annapolis
4.99 out of 5 average rating, 126 reviewsNew Downtown Annapolis Condo With Free Parking
21–28 Nov
Apartment in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
26 Nov – 3 Dec
Apartment in Occoquan
4.93 out of 5 average rating, 392 reviewsThe Daisy in Historic Occoquan (Mins to DC)
17–24 Mar
Apartment in Arlington
4.88 out of 5 average rating, 191 reviewsNewly Renovated & Modern 1BR Condo - Unit 1
21–28 Jan
Apartment in Annapolis
4.96 out of 5 average rating, 147 reviewsThe Crow's Nest - Excellent downtown Annapolis Apt
10–17 Jul
Apartment in Burtonsville
4.93 out of 5 average rating, 198 reviewsRancho Relaxo! A Southwest styled Casita!
30 Dec – 6 Jan
Apartment in Oxford
4.98 out of 5 average rating, 112 reviewsCozy Oxford Getaway
27 Jul – 3 Aug
Apartment in Baltimore
4.91 out of 5 average rating, 113 reviewsSun House in Hampden Private Apartment no stairs
12–19 Feb
Quick stats about holiday rentals that are kid-friendly in Annapolis
Total rentals
90 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
4.9K reviews
Nightly prices starting at
€ 65 before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
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- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals United States
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