Family-friendly holiday rentals in Annapolis
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Annapolis
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 Annapolis family-friendly rentals
Family-friendly home rentals with a hot tub
Bungalow in Deale
4.86 out of 5 average rating, 355 reviewsCozy waterfront getaway on the Bay
22–29 Jan
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
6–13 Feb
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
19–26 Oct
Townhouse in Baltimore
4.95 out of 5 average rating, 570 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
20–27 Aug
Home in Edgewater
4.75 out of 5 average rating, 269 reviewsEdgewater/Mayo Getaway!
13–20 May
Home in Deale
4.98 out of 5 average rating, 113 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
10–17 Jul
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
20–27 Oct
Cabin in North East
4.96 out of 5 average rating, 152 reviewsWaterfront Cabin on the Chesapeake
15–22 Apr
Family- and pet-friendly home rentals
Guest house in Glen Burnie
4.81 out of 5 average rating, 155 reviewsPrivate 1 bedroom house
24–31 Dec
Home in Glen Burnie
4.97 out of 5 average rating, 396 reviewsSecluded acre near BWI and Baltimore
21–28 Aug
Cabin in Gambrills
4.89 out of 5 average rating, 140 reviewsRelaxing Cabin Get Away Near Annapolis & DC
10–17 Aug
Flat in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
5–12 Oct
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
15–22 Feb
Guest suite in Chestertown
4.99 out of 5 average rating, 191 reviewsBeautiful Waterfront Chestertown Getaway
13–20 Sep
Guest suite in Upper Marlboro
4.95 out of 5 average rating, 104 reviewsPrivate Apartment on a Horse Farm
11–18 Jul
Flat in Baltimore
4.86 out of 5 average rating, 784 reviewsStay in a Former Fells Point Bar! - Private Studio
9–16 Feb
Family-friendly home rentals with a pool
Guest suite in Catonsville
4.94 out of 5 average rating, 470 reviewsRollingside: Two-Room Guest Suite
10–17 Oct
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
14–21 Sep
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
5–12 Sep
Apartment in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
12–19 Jun
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
14–21 Jan
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
15–22 Nov
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
23–30 Jan
Cabin in Saint Michaels
4.99 out of 5 average rating, 97 reviewsTrue St. Michaels 6 Acre Waterfront w/heated pool
31 Oct – 7 Nov
Quick stats about holiday rentals that are family-friendly in Annapolis
Total rentals
440 properties
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
140 properties allow pets
Total number of reviews
16K reviews
Nightly prices starting at
€ 37 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
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals United States
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