Family-friendly holiday rentals in Windsor and Maidenhead

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windsor and Maidenhead family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Flat
5 out of 5 average rating, 26 reviews

Spacious 2BR w/ Jacuzzi and Garden!

DavidRating, 5 stars1 week ago
We really enjoyed our time in London. The airbnb is located in a fine area, walkable and close to bus and tube stops. Any store or restaurant you may need is close by. The unit has 2 bedrooms and the bathroom is roomy and good. The kitchen allows you to prepare meals. There was a party next door and the neighbors were loud and obnoxious. But that's the nature of living close to each other. Thanks Reggie, your place worked out well for us.
Superhost
Flat
4.33 out of 5 average rating, 6 reviews

2-Bedroom Windsor Apartment with parking / 15CC

LisaRating, 5 stars3 months ago
Great property and will definitely use for future stays with my clients.
Home
4.88 out of 5 average rating, 8 reviews

Beautiful Home in Great location

JeffreyRating, 5 stars21 months ago
We thoroughly enjoyed the house and location. Although not Sians issue, construction near the train station makes it difficult to get into town by taxi because you have to go around the city. However, if you don’t mind walking and bicycling, there are exceptional bike and walking paths right out to the house from Oxford. I’d stay again in a heart beat.
Top guest favourite
Flat
4.97 out of 5 average rating, 71 reviews

Modern Apartment, 2min to Belsize Park Station

MariaRating, 5 stars1 month 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
4.8 out of 5 average rating, 179 reviews

Lovely 2 bedroom penthouse, Kings Cross St Pancras

KristenRating, 5 stars1 month ago
Great space for a family. We would consider staying again.
Top guest favourite
Apartment
5 out of 5 average rating, 33 reviews

Excellent 2 Bed/1 Bath Flat in Zone 2

FedericoRating, 5 stars2 weeks 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
4.93 out of 5 average rating, 553 reviews

White Cottage Annexe with riverside garden hot tub

JackRating, 5 stars2 weeks ago
Just arrived home from a wonderful two night stay at Sally’s annexe. Where to begin, the annexe itself was full of character, cosy and had everything you could possibly need for a getaway. Robes and sliders for the hot tub provided, lots of lighting, a very well stocked kitchen and a lovely private front area where me and my partner Zoë enjoyed sitting in the evening with a log fire and bbq. The settings and garden, not to mention the cottage are beautiful, we’ve never felt peace like it. Lots of beautiful walks, pubs and restaurants nearby and plenty of great recommendations from Sally too. Sally made us feel at home instantly and gave us a tour during check in so we knew exactly where to find everything. Beau the cat was just the cherry on the cake. Host, home and surroundings, just lovely. Also the bed in the annexe may be the comfiest we’ve stayed in. Would visit again in a heartbeat, if you want a quiet break from the city. This is the place.
Top guest favourite
Place to stay
4.97 out of 5 average rating, 92 reviews

Luxury log Cabin, Nr Horsham, W. Sussex, & Hot Tub

DanielRating, 5 stars1 week ago
Private & Beautiful location and stunning well appointed home/cabin; friendly, responsive host. We were made to feel at home. Will definitely visit again. Thanks Claire

Family- and pet-friendly home rentals

Top guest favourite
Flat
4.95 out of 5 average rating, 187 reviews

Stylish Apartment in Kensal Rise (Near Portobello)

FrancescaRating, 5 stars1 week ago
Thank you for being able to use your lovely flat. We found it beautifully clean and tidy and easy to use. We would highly recommend a stay in this flat for a visit to London.
Guest favourite
Home
4.87 out of 5 average rating, 148 reviews

Newly Refurbished Large Family Home-6 min to Tube

JaneRating, 5 stars1 week ago
Jubed is more than a host… he is a friend to his guests. He went out of his way to help is. with any need or travel emergency. The townhouse is beautiful and Jubed adds the extra little touches that make you feel like valued friends rather than just guests. I will definitely return to Stanmore street the next time I visit London! Jane G
Guest favourite
Cottage
4.94 out of 5 average rating, 172 reviews

Self contained, rural cottage, 2 double bedrooms

DeeRating, 5 stars1 week ago
What a great setting for an escape to the country! I already miss waking up with the chickens and pigs to greet me every day. I also saw more wild animals and birds in my walks around here in a week, than I have in years in London. Auriol is a great host, relaxed, knowledgeable and friendly, and the property is exactly as described and shown here. Tips for other travelers: If you’re a light sleeper bring an eye mask and earplugs as it does get sunny in the main bedroom. Looking forward to returning here!
Superhost
Guest house
4.89 out of 5 average rating, 149 reviews

The Old Hay Barn, Ashley Green

GavinRating, 5 stars1 month ago
Very cozy, comfortable, beautiful house. Lovely walks nearby, especially for dogs. Very friendly hosts. Thoroughly recommended
Guest favourite
Cottage
4.96 out of 5 average rating, 122 reviews

Modern Cottage with Rural Views - Remote Location

MeghanRating, 5 stars3 weeks ago
Such a lovely home, we didn't want to leave! Hosts were excellent communicators and also very warm and kind people. Loved our walks along the canal and peaceful surroundings. We will be back!
Top guest favourite
Home
4.97 out of 5 average rating, 211 reviews

Getaway Cottage Windsor

SarahRating, 5 stars1 week ago
We stayed at The Clockhouse whilst visiting Windsor Castle. We would not hesitate to stop there again. Beautiful place, very peaceful. Very comfortable and nicely decorated. Fantastic stay! Thank you, Sam x
Top guest favourite
Guest house
4.91 out of 5 average rating, 138 reviews

Charming cottage in Shalford, in the Surrey Hills

KerenRating, 5 stars1 month ago
Back again. My home away from home when visiting Shalford. The cottage is charming and so serene and quiet. Amanda and Ben and the dogs are all so welcoming.
Guest favourite
Barn
4.92 out of 5 average rating, 123 reviews

Hazel - Heath Row Barn

JaneRating, 5 stars1 week ago
Thoroughly enjoyed are return stay at this lovely gem in the Hampshire countryside. Thanks Emilie for being understanding about the crack in the cafetière! Would highly recommend this place for anyone wanting a tranquil location . The apartment is very homely and has all you need for a stay away from home. We hope to return here soon.

Family-friendly home rentals with a pool

Superhost
Cottage
4.87 out of 5 average rating, 47 reviews

The Cottage, dog friendly,swimming pool in summer

OliverRating, 5 stars33 months ago
Miranda's cottage is very well situated and set up for doing as we did - enjoying the local area, taking advantage of hot summer days by the pool, and walking in the woods with kids. Highly recommended for families of 4 or even more if you're prepared to really use the space. My kids were very happy sleeping in the twin beds, and we were able to use every inch of the place.
Superhost
Apartment
4.85 out of 5 average rating, 410 reviews

Luxury Battersea studio w open fire, close to Park

KarenRating, 5 starstoday
Although the entrance from the street is a bit old looking, once the apartment door is opened, one realizes what a wonderful spot it is. There were all the amenities I needed, the bed and couch were quite comfortable. It was a great walk to my office across the river. (and of course, Battersea park is very closeby). The host was very responsive to my questions. I hope the apartment is available the next time I am in London!
Superhost
Guest suite
4.74 out of 5 average rating, 151 reviews

Private garden studio with use of pool

RachelRating, 5 stars7 months ago
Great spot if you're using public transportation in London. There's a bus stop a short walk away. Friendly hosts, beautiful yard!
Guest favourite
Cottage
4.94 out of 5 average rating, 195 reviews

Beautiful S.Downs Cottage, pool and tennis

CharlieRating, 5 stars2 weeks ago
If you are looking for a home from home or an upgrade from home, this is the place to stay. Arrived from Melbourne and immediately settled into the joy of living in the countryside. Although too cold to enjoy the pool, we did use the tennis court and shot some hoops. We walked to Old Thorns Golf and Country Club and can recommend Katie's Coffee bar. It's an easy walk amongst stunning scenery. We walked back via the Foley Estate from the Deers Hut pub. Liphook is so lucky to have not one but two stunningly beautiful golf courses. If their is a heaven on earth, we must have stayed in its guest house!
Superhost
Home
4.87 out of 5 average rating, 223 reviews

Barn conversion, Henley-on-Thames

MartinRating, 5 stars6 months ago
We were a family party with ages from 5 to 75 . Lots for everyone to do ( swimming , tennis, billiards/snooker & beautiful walks all there) There was enough space both inside the wonderfully converted barn and outside in the extensive grounds to enjoy each others company without being overcrowded. Thanks Sarah for enabling a lovely weekend .
Guest favourite
Place to stay
5 out of 5 average rating, 8 reviews

Romantic Swedish cabin in magical setting

JackRating, 5 stars1 month 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.
Top guest favourite
Guest house
4.94 out of 5 average rating, 232 reviews

Bucks Green Place Beautiful Converted Barn

JillRating, 5 stars1 month ago
We had a lovely stay, the little house was clean, cosy and warm, everything you need, we explored the area for walks. We walked to the local pub , The Fox Inn they where very friendly the food was nice. We went to the Parrot at Forest Green for a Sunday Roast which was great. Horsham is near if you fancy a potter around the shops and pick up some bits. Guildford was 30 minutes away also another lovely day there too. Thank you we enjoyed our visit.
Superhost
Townhouse
4.65 out of 5 average rating, 54 reviews

Stylish 3-bedroom Clapham Family Home + Office

PennyRating, 5 stars6 months ago
We had a fabulous long stay in Susan’s house. The house was perfect, spacious and homely and in a great location near Clapham high st and Clapham common with lots of nice shops, parks and close to lots of public transport. Susan was very welcoming and responsive and went above and beyond to make us comfortable and help us during our stay.

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