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Family-friendly holiday rentals in Windsor and Maidenhead

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Windsor and Maidenhead family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Flat in West Kensington
4.93 out of 5 average rating, 29 reviews

Spacious 2BR Retreat w/ Jacuzzi and Garden!

SafaRating, 5 stars1 week ago
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!
Top guest favourite
Flat in Camden
4.97 out of 5 average rating, 71 reviews

Modern Apartment, 2min to Belsize Park Station

MariaRating, 5 stars3 months ago
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.
Superhost
Flat in Camden
4.81 out of 5 average rating, 188 reviews

Lovely 2 bedroom penthouse, Kings Cross St Pancras

JessRating, 5 stars2 weeks ago
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!
Flat in Wandsworth
4.78 out of 5 average rating, 18 reviews

Lovely 3-bedroom flat in Battersea

AlexRating, 5 stars70 months ago
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.
Apartment in Southwark
4.95 out of 5 average rating, 21 reviews

++Stylish&Cozy 1BR Flat near Waterloo station++

CarlosRating, 5 stars22 months ago
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.
Top guest favourite
Apartment in London
5 out of 5 average rating, 33 reviews

Excellent 2 Bed/1 Bath Flat in Zone 2

FedericoRating, 5 stars2 months ago
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!
Guest favourite
Guest house in The Ayots
4.93 out of 5 average rating, 563 reviews

White Cottage Annexe with riverside garden hot tub

LouiseRating, 5 stars1 week ago
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.
Top guest favourite
Cottage in Baughurst
4.96 out of 5 average rating, 370 reviews

Luxury rural thatched cottage with cedar hot tub.

SohrabRating, 5 stars2 weeks ago
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

Top guest favourite
Flat in Pamber Green
4.9 out of 5 average rating, 145 reviews

Self Contained Annex

V MRating, 5 stars5 days ago
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.
Top guest favourite
Bungalow in Tutts Clump
4.96 out of 5 average rating, 299 reviews

Garden Cottage..pretty countryside location

Caron & DaveRating, 5 stars1 week ago
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.
Superhost
Home in Crondall
4.85 out of 5 average rating, 124 reviews

2 Storey Coach House Crondall, 2 KING bed, 2 bath

DaveRating, 5 stars1 week ago
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.
Top guest favourite
Cottage in Brill
4.88 out of 5 average rating, 127 reviews

Elegant Countryside Cottage near Oxford

JamesRating, 5 stars2 weeks ago
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.
Guest favourite
Guest house in Surrey
4.94 out of 5 average rating, 239 reviews

14th Century Dairy

VivienneRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Ibworth
4.94 out of 5 average rating, 175 reviews

Self contained, rural cottage, 2 double bedrooms

HannahRating, 5 stars1 month ago
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!
Guest favourite
Flat in Richmond
4.93 out of 5 average rating, 100 reviews

Chic Apartment Retreat Close to Richmond Park

MariaRating, 5 stars6 days ago
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🤗
Guest favourite
Chalet in Benson
4.91 out of 5 average rating, 282 reviews

Mizpah Ecolodge

GerardRating, 5 stars1 month ago
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

Superhost
Apartment in Wandsworth
4.85 out of 5 average rating, 416 reviews

Luxury Battersea studio w open fire, close to Park

StephanieRating, 5 stars1 week ago
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!
Superhost
Guest suite in Lambeth
4.74 out of 5 average rating, 156 reviews

Private garden studio with use of pool

GaryRating, 5 stars3 weeks ago
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
Top guest favourite
Cottage in Buckinghamshire
4.97 out of 5 average rating, 355 reviews

Family friendly - rural, detached, home from home

SarahRating, 5 stars4 days ago
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
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 226 reviews

Barn conversion, Henley-on-Thames

AndrewRating, 5 stars4 days ago
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.
Guest favourite
Place to stay in Shere
5 out of 5 average rating, 8 reviews

Romantic Swedish cabin in magical setting

JackRating, 5 stars2 months ago
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.
Superhost
Home in Yarnton
4.79 out of 5 average rating, 19 reviews

Converted Stables on the Edge of the Cotswolds

EmilyRating, 5 stars2 months ago
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!
Top guest favourite
Guest house in Rudgwick
4.94 out of 5 average rating, 234 reviews

Bucks Green Place Beautiful Converted Barn

GloeRating, 5 stars1 month ago
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.
Guest favourite
Barn in Woking
4.96 out of 5 average rating, 142 reviews

Luxury Barn

AnnabelleRating, 5 stars2 months ago
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

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