Family-friendly vacation 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.
Vacation 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
4.87 out of 5 average rating, 356 reviewsCozy waterfront getaway on the Bay
Dec 22 – 29
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Apr 29 – May 6
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Home in Edgewater
4.76 out of 5 average rating, 270 reviewsEdgewater/Mayo Getaway!
Aug 23 – 30
Home in Deale
4.98 out of 5 average rating, 113 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
Oct 23 – 30
Townhouse in Baltimore
4.95 out of 5 average rating, 572 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Aug 23 – 30
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Oct 30 – Nov 6
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Jan 16 – 23
Family- and pet-friendly home rentals
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 156 reviewsPrivate 1 bedroom house
Aug 24 – 31
Apartment in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
Sep 12 – 19
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
Feb 8 – 15
Home in Glen Burnie
4.97 out of 5 average rating, 399 reviewsSecluded acre near BWI and Baltimore
Oct 15 – 22
Guest suite in Upper Marlboro
4.95 out of 5 average rating, 104 reviewsPrivate Apartment on a Horse Farm
Jul 16 – 23
Guest suite in Chestertown
4.99 out of 5 average rating, 193 reviewsBeautiful Waterfront Chestertown Getaway
Jul 9 – 16
Home in Cambridge
4.89 out of 5 average rating, 111 reviewsDorothy's Chesapeake Delight
Oct 19 – 26
Apartment in Baltimore
4.86 out of 5 average rating, 787 reviewsStay in a Former Fells Point Bar! - Private Studio
Feb 11 – 18
Family-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Sep 6 – 13
Guest suite in Catonsville
4.94 out of 5 average rating, 470 reviewsRollingside: Two-Room Guest Suite
Oct 5 – 12
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Jan 29 – Feb 5
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Oct 15 – 22
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 22 – 29
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
Apr 8 – 15
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
Jan 10 – 17
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Jan 22 – 29
Quick stats about vacation 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
R740 ZAR before taxes and fees
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Washington
- Family-friendly rentals Baltimore
- Rentals with breakfast Annapolis
- House rentals Annapolis
- Condo rentals Annapolis
- Rentals with pools Annapolis
- Apartment rentals Annapolis
- Rentals with a patio Annapolis
- Rentals with lake access Annapolis
- Private suite rentals Annapolis
- Pet-friendly rentals Annapolis
- Waterfront rentals Annapolis
- Rentals with outdoor seating Annapolis
- Monthly Rentals Annapolis
- Fitness-friendly rentals Annapolis
- Rentals with a fire pit Annapolis
- Rentals with a hot tub Annapolis
- Townhouse rentals Annapolis
- Rentals with an EV charger Annapolis
- Kid-friendly rentals Annapolis
- Rentals with beach access Annapolis
- Rentals with a washer and dryer Annapolis
- Rentals with a fireplace Annapolis
- Family-friendly rentals Maryland
- Family-friendly rentals Anne Arundel County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom