
Family-friendly holiday rentals in Windsor and Maidenhead
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windsor and Maidenhead
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 Windsor and Maidenhead family-friendly rentals
Family-friendly home rentals with a hot tub

Spacious 2BR Retreat w/ Jacuzzi and Garden!
Reggie is by far one of the most attentive, helpful, and kind hosts I’ve ever encountered. His exceptional hospitality truly exceeded my expectations and made my stay unforgettable. I was genuinely surprised—in the best way—by how thoughtful and accommodating he was. Thank you so much, Reggie!

Modern Apartment, 2min to Belsize Park Station
Carol Anne and Kelly were great hosts, kind and helpful. The apartment was very nice, equipped with everything we needed and very comfortable. The location is excellent, very close to the subway and buses, the neighborhood is great. We had a great time, thaks a lot.

Lovely 2 bedroom penthouse, Kings Cross St Pancras
Our short stay at Debbie’s flat was so good! She let us pay £10 per each hour before check in time which was so worth it as we arrived with 4 kids in the morning so it was nice to check in around 11 and get our bags settled so we could spend the rest of the day exploring! The flat was so cute and free of clutter, comfortable, and such easy walking distance from Kings Cross so it was very easy to get around. The neighborhood was quiet and safe and we would honestly want to stay there again if we make our way back to London! Thank you so much for everything!

Lovely 3-bedroom flat in Battersea
A great home in a great location for london. We stayed with small children for 2 weeks and the home was perfectly set up for our family with toys, a safety gate, cot, bath and washing machine. The local parks and commons were fantastic. François was a very attentive and generous host, giving us lots of information and responding quickly and thoroughly to any queries. We felt very welcomed and at home.

++Stylish&Cozy 1BR Flat near Waterloo station++
Simple but very practical apartment, with all the necessary equipment to spend a few days. You can tell that Yura is a very thoughtful person since there was nothing missing. The location of the apartment is exceptional, very well connected and a few minutes from downtown.

Excellent 2 Bed/1 Bath Flat in Zone 2
Absolute lovely place in a quiet area of London. The flat is exactly as described and it has everything you need for a short or long stay. Totally recommended, would love to come back!

White Cottage Annexe with riverside garden hot tub
Beautiful gardens quaint cottage. Annex rustic and serviceable. Different pictures on line. Courtyard looked very different as did the funiture in the front room. The bathroom needs updating bit too rustic for me but thats my opinion. Very comfortable and outside is outstanding.

Luxury rural thatched cottage with cedar hot tub.
My friends and I enjoyed a peaceful couple of nights in Jean and Kieth's beautiful cottage. Keith was friendly and helpful with clear instructions. the cottage is gorgeous and the garden is lovely! I would definitely stay there again.
Family- and pet-friendly home rentals

Self Contained Annex
Thoroughly enjoyed our stay and will hopefully return. Our hosts were a delight and exceptionally helpful and friendly.. The location is amazing. We were watching red kites in flight and even heard a cuckoo. Lots of walking trails nearby too. Would definitely recommend a visit.

Garden Cottage..pretty countryside location
Tracey's place was perfect for ourselves, our daughter and two dogs. A surprisingly private and peaceful location, yet within easy reach of facilities, pubs, restaurants and (important for us) Newbury Show-ground. Comfortable, well appointed and presented accommodation, with a generous welcome pack. Great for our dogs too, with a secure outdoor area. Would definitely be happy to come again. Thanks.

2 Storey Coach House Crondall, 2 KING bed, 2 bath
Great spot in the countryside, but close enough to Farnham to be convenient for visiting our family there. This was our second stay and we would love to return next time we visit.

Elegant Countryside Cottage near Oxford
A most pleasing cottage in a superb setting of an idealistic English village. Hosts excellent A cosy living area and spacious bedroom with adjoining dressing room leading to a superb bathroom with high quality curved glass shower cubical. In short the nicest private accommodation out of dozens we have enjoyed.

14th Century Dairy
I had a wonderful stay in this charming place. A place to totally relax and let go in the beautiful countryside. I would highly recommend staying in such a special place.

Self contained, rural cottage, 2 double bedrooms
We stayed at The Twig whilst visiting family in the area and it was absolutely perfect for our needs. The cottage was spacious, clean and the animals were an added bonus especially for our 3 year old daughter. We will definitely be back when next visiting the area, thank you!

Chic Apartment Retreat Close to Richmond Park
We had such a wonderful time. The flat has absolutely everything you need and plenty more. The art, the plants, the books and the decor make it a very special place. Situated close to the beautiful Terrace Gardens and Richmond Park and with cafes , pubs and convenience stores steps away you will not be disappointed. Easy walk down the hill to the station and everything Richmond has to offer. James was absolutely charming and super helpful. Highly recommend🤗

Mizpah Ecolodge
Had another great stay at the eco lodge. Ideally placed outside Wallingford in lovely countryside and convenient for the Ridgeway and associated places. The eco lodge is private with its own parking and despite the roasting weather the week we were there, it kept a comfortable temperature inside. lovely big bed, excellent space to relax and with it's own kitchen and bathroom and all the amenities you could want. Kunzi the owners friendly cat is on hand to meet and greet and the field adjacent the front of the lodge is alive with wildlife. It's a great place to relax or use as a base for exploration. Recommend Wallingford and Henley on Thames for exploration and the Ridgeway for great walking and scenic views.
Family-friendly home rentals with a pool

Luxury Battersea studio w open fire, close to Park
How to start?? I would highly recommend Charles' place! When you get there and go up the stairs, you might think it's not going to be good. However, when you open the door you'll be taken back as to how beautiful his place is!! I felt right at home! Charles had wine, milk, OJ, bread and eggs. The sleigh bed was not only comfy but so pretty. He had great darkening curtains which also serve as a divider from the living room. The shower was welcoming. If I come back to London, I'd stay at Charles' place!

Private garden studio with use of pool
Fantastic stay, hosts were brilliant and went out way to make me feel welcome, lovely to have use of the pool, nice walk from streathem station over the common and lovely neighbourhood, highly recommend

Family friendly - rural, detached, home from home
A fabulous country cottage within large gardens including a pretty waterlily pond & beautiful wildflower meadow. Lovely views & country walks on the doorstep. Very welcoming, friendly hosts made us feel at home straight away. Idyllic! The bed was super comfy too! We’d definitely recommend this property & stay again. Thank you Karen & Phil

Barn conversion, Henley-on-Thames
A beautiful barn conversion in lovely grounds with lots of facilities, with thoughtful and helpful hosts. It was a fabulous long weekend and we didn’t need to leave the grounds to be entertained throughout, from in the pool to playing pool, it was all we could ask for.

Romantic Swedish cabin in magical setting
Emma was very welcoming as we arrived. She showed us around and gave us perfect advice on how to get into town. The cabin was perfect for a weekend away. We found a swing attached to the trees and had great fun. The bed was like a cloud and the kitchen had everything you need. Would recommend to family and would stay again.

Converted Stables on the Edge of the Cotswolds
What a wonderful place to stay! We had a great weekend at stable cottage, location exactly as described, beautiful setting and really comfy beds! The amenities in the place were great and we really enjoyed the log fire in the evenings. Would definitely recommend!

Bucks Green Place Beautiful Converted Barn
A home from home - ideal for either a short or long stay. Exceptionally well equipped, with everything you might need. Very clean and comfortable, in a delightful and secure and private setting. Rebecca was very welcoming and on hand if we needed anything. The best Airbnb we've stayed in and would definitely return when we are next in the West Sussex area.

Luxury Barn
Another lovely weekend break at The Barn. It's a perfect space for our group of friends to catch up and chill out. Always spotless and clean. We lucked out with the weather and the pool and tennis court got some good use. We had a lovely 6 mile walk around the Surrey Hills with the beautiful Abinger Hatch pub a half way point. Daniel was very welcoming and friendly and accessible to answer our queries. Kitchen is well stocked with utensils and crockery but we forgot cling film and foil, so bring some if you think you will be using it. There is a lovely outdoor seating area and dining table which was a lovely afternoon sun trap. All in all a perfect stay and we will be coming again next year!
Quick stats about holiday rentals that are family-friendly in Windsor and Maidenhead
Total rentals
1.2K properties
Total number of reviews
31K reviews
Pet-friendly rentals
320 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
490 properties have a dedicated workspace
Wifi availability
1.2K properties include access to wifi
Destinations to explore
- River Thames Holiday rentals
- Royal Borough of Kensington and Chelsea Holiday rentals
- London Borough of Camden Holiday rentals
- City of Westminster Holiday rentals
- London Holiday rentals
- Central London Holiday rentals
- Regent's Canal Holiday rentals
- London Borough of Islington Holiday rentals
- South London Holiday rentals
- City of London Holiday rentals
- Oxford Holiday rentals
- Inner London Holiday rentals
- Rentals with a washing machine and dryer Windsor and Maidenhead
- Rentals with lake access Windsor and Maidenhead
- Smoking-friendly rentals Windsor and Maidenhead
- Fitness-friendly rentals Windsor and Maidenhead
- Family-friendly rentals Windsor and Maidenhead
- Pet-friendly rentals Windsor and Maidenhead
- Townhouse rentals Windsor and Maidenhead
- Hotel rentals Windsor and Maidenhead
- Waterfront rentals Windsor and Maidenhead
- Cabin rentals Windsor and Maidenhead
- Rentals with a fireplace Windsor and Maidenhead
- Rentals with an EV charger Windsor and Maidenhead
- Guest house rentals Windsor and Maidenhead
- Flat rentals Windsor and Maidenhead
- House rentals Windsor and Maidenhead
- Rentals with a patio Windsor and Maidenhead
- Rentals with breakfast Windsor and Maidenhead
- Rentals with outdoor seating Windsor and Maidenhead
- Private suite rentals Windsor and Maidenhead
- Bed and breakfasts Windsor and Maidenhead
- Rentals with pools Windsor and Maidenhead
- Rentals with a firepit Windsor and Maidenhead
- Rentals with a hot tub Windsor and Maidenhead
- Serviced apartment rentals Windsor and Maidenhead
- Cottage rentals Windsor and Maidenhead
- Apartment rentals Windsor and Maidenhead
- Family-friendly rentals Berkshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- 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
- British Museum
- Green Park
- Buckingham Palace
- Covent Garden
- Big Ben
- Trafalgar Square
- Barbican Centre
- Harrods
- Tower Bridge
- London Bridge
- St. Paul's Cathedral
- Brockwell Park
- The O2
- Camden Market
- Emirates Stadium
- Wembley Stadium
- The Shard
- Hampstead Heath
- ExCeL London
- London Stadium
- River Lee Navigation
- Alexandra Palace
- Queen Elizabeth Olympic Park, London
- Oxford University