Some info has been automatically translated. Show original language

Kid-friendly holiday rentals in Annapolis

Find and book unique family-friendly rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Annapolis family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Annapolis
4.99 out of 5 average rating, 86 reviews

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

ChadRating, 5 stars1 week ago
The house is easy to find and has a great outdoor seating area. The house and linens were very clean and Sekai even provided fresh fruit upon arrival! The stocked Kurig pods were very handy and appreciated in the morning as well. From this location you have easy access to downtown Annapolis and all of its history. If you go the other way out of the neighborhood, you can browse the mall and TownCentre for all your other shopping needs. This is a pet friendly house that you would not know there had ever been a dog in there. Fortunately, ours was well behaved so you still won't know a pet was ever there! He enjoyed walking the large private yard.
Guest favourite
Home in Annapolis
4.97 out of 5 average rating, 74 reviews

Annapolis USNA Cottage Waterfront Pier Cozy Escape

Nate And KatieRating, 5 stars2 weeks ago
Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities
Guest favourite
Home in Annapolis
4.99 out of 5 average rating, 74 reviews

Captain’s Retreat! Newly Renovated - Beach House!

LisaRating, 5 stars2 weeks ago
plenty of towels. Great accomodations for a family wedding. Cards and games were available and appreciated.
Top guest favourite
Home in Annapolis
4.98 out of 5 average rating, 109 reviews

Villa Annapolitana • Parking 1 min • USNA 4 min

LaRaeRating, 5 stars2 weeks ago
We had a great stay for CW25! The location is ideal for easy access to USNA and all that downtown has to offer. The home was exceptionally well appointed and spotless . The decor is beautiful Beds /linens were all very comfortable ( with a huge variety of pillow options which was so appreciated !)and the blackout shades in the bedrooms made for a great nights sleep.Kate is a wonderful and responsive host. We highly recommend this beautiful home!
Guest favourite
Home in Arnold
4.98 out of 5 average rating, 42 reviews

Rachel's BnB

WendyRating, 5 stars5 days ago
Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 12 reviews

Historic Downtown Annapolis Gem

BethanyRating, 5 stars2 weeks ago
This home is right in downtown Annapolis. You can walk to many historic sites, restaurants, and bars. There is no parking, so you must park in one of the garages and walk to the house - but it isn't far. Street parking is limited to 2 hours for non-permit holders. This was one of my favorite airbnbs in Annapolis (and I've stayed in many). It was exactly as pictured/described. It was bigger than expected with lots of space for a larger group. The living room was nice with lots of seating and a large tv. We used the pullout sofa in the second living area and it was super comfortable. The bedrooms and bathrooms were very nice - great showers and deep soaker tub in the en suite. I slept in the king bed in the back bedroom and it was wonderful. The kitchen and dining area were very nice and we gathered there much of the time. We enjoyed the front porch for morning coffee and evening drinks. The back patio was also another nice space to sit and relax.
Guest favourite
Home in Annapolis
4.94 out of 5 average rating, 418 reviews

New Hotel Chic

TeresaRating, 5 stars1 day ago
Cannot say enough great things! Incredibly understanding, great communication and loved the space! 100% recommend!
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars1 week ago
Beautiful place, beautiful location. Joel thought of anything you could want.

Family-friendly apartment rentals

Guest favourite
Flat in Upper Marlboro
4.95 out of 5 average rating, 131 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

JasonRating, 5 stars6 days ago
This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.
Superhost
Flat in Glen Burnie
4.84 out of 5 average rating, 461 reviews

Quiet Cozy 1 Bdr Apt at BWI Airport

EmilyRating, 5 stars2 weeks ago
Penny is an incredible host who really goes above and beyond! I greatly enjoyed my stay.
Superhost
Flat in Silver Spring
4.92 out of 5 average rating, 444 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

AndrewRating, 5 stars1 month ago
Very responsive host. The side yard is very nice for people with dogs that travel. Location is very nice but DC traffic during rush hour can be rough but this can be planned for. Would stay again.
Top guest favourite
Flat in Essex
4.97 out of 5 average rating, 270 reviews

A unique place on sue creek

DanilleRating, 5 stars6 days ago
Had a great time! Kathy and wayne was very helpful on suggesting restaurants and things to do. We loved the dock and fishing! They made sure we was right at home when we interacted with. This was a good central place to all we wanted to see, we went to Hersey Pa. Washington dc., The beach(bay) area, Baltimore harbor.
Guest favourite
Flat in Arnold
4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

JennaRating, 5 stars9 months ago
Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.
Guest favourite
Flat in Baltimore
4.94 out of 5 average rating, 531 reviews

Urban 1-Bedrm. Apt. Overlooking Union Square Park

IyanaRating, 5 stars4 days ago
Anne’s place was great for my week long stay in Baltimore. It was about 17 minutes from JHU, less than 15 minutes from the Harbor and National Aquarium, close to Baltimore local favorites, and directly across from a park. Anne was responsive to all my concerns and needs. The apartment was clean and had an abundance of extra towels and sheets for our use. The only comment I have is about the TV and Wifi which were both slow and lagged when doing work. Everything else was perfect and I would definitely stay there again.
Superhost
Flat in Annapolis
4.87 out of 5 average rating, 287 reviews

Gybeset Eastport Inn

JillRating, 5 stars3 weeks ago
Great place to stay in Eastport. A couple doors down from Vin 909 Winecafe, which we highly recommend.
Top guest favourite
Flat in Annapolis
4.96 out of 5 average rating, 148 reviews

Charming lower-level apartment in Annapolis

SophiaRating, 5 stars3 weeks ago
Joyce is a one in a million host, but more importantly, a one in a trillion person... I'm beyond grateful to have had the opportunity to meet her and Nicole. Thank you Joyce for welcoming me with open arms and making my stay in Annapolis an unforgettable experience. Already looking forward to when our paths cross again. Sending you and your family blessings <3

Family-friendly apartment rentals

Guest favourite
Apartment in Occoquan
4.92 out of 5 average rating, 769 reviews

The Bird's Nest in Historic Occoquan (Mins to DC)

StacyRating, 5 stars3 weeks ago
Our stay at Occaquan was peaceful, relaxing, and very much needed. Arriving to the parking lot was a breeze, only because if John's specific instructions to find it, that was very much appreciated after a long drive. Walking into the place, first impression, looks just like the picture. The very next thought, "how cute is this". From the beautiful window behind the couch with a lovely tree to watch birds in to the cozy feeling of being in a familiar place. This place is quiet, surrounded with beautiful historic scenery, and has many local shops and vendors to spend an afternoon exploring. We walked down to the park by the water way and learned some history while soaking up the sun and the breeze of nature. I absolutely recommend John's place for a stay. I know I will be returning for a simple, relaxing get away, once again! Thank you John for everything!
Top guest favourite
Apartment in Annapolis
4.99 out of 5 average rating, 148 reviews

New Downtown Annapolis Condo With Free Parking

GailRating, 5 stars2 weeks ago
Ellen’s condo was absolutely perfect for Commissioning Week. The location couldn’t have been better—within walking distance to fantastic restaurants, the Naval Academy, and Graduation at the Navy-Marine Corps Memorial Stadium. The coffee shop downstairs was a delightful bonus, and the underground parking was a major perk. Ellen provided clear and detailed instructions about the condo and guest expectations, making everything easy to understand and stress-free. The condo itself is beautifully and tastefully furnished, with all the essentials thoughtfully provided. The in-unit washer and dryer were a huge convenience. The bathroom was spacious and well-appointed, complete with shampoo, conditioner, and body wash. What I appreciated most was how quiet and peaceful the condo was—it offered a true retreat. The private patio was perfect for enjoying a morning coffee or an afternoon cocktail. I would absolutely stay here again.
Guest favourite
Apartment in Annapolis
4.94 out of 5 average rating, 397 reviews

Brand New Reno in Historic Dist w 2 Parking spots

MitchRating, 5 stars2 weeks ago
We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.
Guest favourite
Apartment in Burtonsville
4.93 out of 5 average rating, 240 reviews

Rancho Relaxo! A Southwest styled Casita!

IanRating, 5 stars6 days ago
Quiet location. Nicely decorated. Abaad was very responsive. I enjoyed my stay.
Guest favourite
Apartment in Mount Vernon
4.94 out of 5 average rating, 150 reviews

Live-in Arcade in Mount Vernon w/Free Parking

JessRating, 5 stars1 month ago
Jordan and his place were both amazing. As avid gamers ourselves, this was a walk down memory lane. All linens and kitchen ware were available. You can cast your apps on the Google TVs, which is a huge bonus. There are tons of food places within 5 minutes walking distance and we were able to to walk to the CFG Bank Arena for a show with in 15-20 min. Saves on parking or Uber/Lyft costs. Jordan is extremely responsive and even recommended local eats. They were delicious. Thanm you so much, Jordan. It was a delight having you as a host.
Guest favourite
Apartment in Oxford
4.98 out of 5 average rating, 127 reviews

Cozy Oxford Getaway

MelanieRating, 5 stars1 week ago
Oxford is my favorite place to visit on the Eastern shore and I love staying in this little place near the town park. it's so peaceful and close to everything. I love connecting with the locals I've met on my travels. I look forward to returning!
Guest favourite
Apartment in Ellicott City
4.88 out of 5 average rating, 104 reviews

Old Ellicott Condo | Historic mid-century home

NicoleRating, 5 stars2 weeks ago
Ben’s place is exactly as described me and my family enjoyed our stay. I felt right at home, when I’m visiting my sister in the near future I will definitely stay again.
Guest favourite
Apartment in Mount Vernon
4.85 out of 5 average rating, 432 reviews

Cozy Private Condo in Mt. Vernon with Rooftop

PaulRating, 5 stars3 days ago
Great location, close to transportation and dining options. Place is very quaint. Uncomplicated entry and exit. Neighborhood walkable and friendly. I would consider staying again.

Quick stats about holiday rentals that are kid-friendly in Annapolis

  • Total rentals

    100 properties

  • Nightly prices starting at

    ₹5,982 before taxes and fees

  • Total number of reviews

    5.7K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore