Family-friendly vacation rentals in Maidenhead

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Maidenhead family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Kingston upon Thames

4.95 out of 5 average rating, 56 reviews

London's Best 5 Bedroom Family Home

NathanRating, 5 stars18 months ago
This is an Airbnb gem! Ryan and Nadya have a beautiful home and were fantastic hosts. Would definitely stay here again, and would highly recommend to families visiting London.

Apartment in Windsor

4.33 out of 5 average rating, 6 reviews

2-Bedroom Windsor Apartment with parking / 15CC

LisaRating, 5 stars3 weeks ago
Great property and will definitely use for future stays with my clients.
Superhost

Home in Nuptown

5 out of 5 average rating, 9 reviews

Fabulous Country House, Pool, Garden, 400mbps

NeilRating, 5 stars40 months ago
Great house perfect for our family gathering & close to transport links that we were using to meet up. Heated pool & hot tub were perfect to use & the large garden with table tennis, trampoline & hammock etc were ideal given the good weather during our trip. Hosts were fantastic providing extra sports equipment for use & were easily reachable throughout & swiftly solved the issue with the pool heater.

Home in Horspath

4.86 out of 5 average rating, 22 reviews

Spacious house in Oxford with media room

KatyRating, 5 stars62 months ago
A wonderful home which made us all thoroughly enjoy our weekend. Great host and ideal for a large group of people to get away and spend some time together. We would definitely rent again!
Guest favorite

Farm stay in Chinnor

4.92 out of 5 average rating, 127 reviews

The Pool House at Upper Farm (near Thame/Oxford)

AlexRating, 5 stars3 months ago
The pool house was perfect in every way, it was very clean and spacious. We had a wonderful relaxing weekend, enjoying the hot tub under the stars was amazing. The pool house is in a lovely location, very peaceful and private. We will definitely be booking to go back again. Thank you Gary and the team for being such great hosts.

Family- and pet-friendly home rentals

Guest favorite

Apartment in Pamber Green

4.91 out of 5 average rating, 140 reviews

Self Contained Annex

ChristinaRating, 5 stars2 weeks ago
Freya was such an excellent host - host, helpful, responsive and friendly. Freya sorted out some extras (cot and high chair) and was so helpful and understanding in all communication. Beautiful accommodation, clean and well kept. The accommodation is a little difficult to find but Freya was on hand to help out and she and her partner were actively looking out for us.
Guest favorite

Bungalow in Tutts Clump

4.95 out of 5 average rating, 275 reviews

Garden Cottage..pretty countryside location

ChrisRating, 5 stars4 weeks ago
Absolutely beautiful property. Tracey was such a wonderful host and left a beautiful basket and even decorated it with Christmas decorations. Seeing as we stayed over Christmas Day and Boxing Day, this really made a difference. Excellent communications throughout and overall a home away from home.
Guest favorite

Cottage in Ibworth

4.95 out of 5 average rating, 168 reviews

Self contained, rural cottage, 2 double bedrooms

HelenRating, 5 stars1 month ago
Such a stunning spot and a beautiful house. The host is so welcoming and the accommodation is so cosy. It is our second visit and we would definitely come again.
Guest favorite

Home in Wraysbury

4.97 out of 5 average rating, 106 reviews

River Thames near Windsor, Heathrow & London

HelanRating, 5 stars1 week ago
Beautiful house in a beautiful location! The sunroom was probably my favorite part of the house. Rebecca was so responsive and accommodated an early checkin. I would recommend a car to get around, especially if you need to get to the train station, otherwise you'll need to walk or use an uber.
Guest favorite

Bungalow in Tidmarsh

4.93 out of 5 average rating, 199 reviews

Self Contained Detached Property on the River Pang

MatthewRating, 5 stars3 weeks ago
My family & I had a wonderful stay at the Annexe, there are lots of lovely walks to do on the doorstep and within 5mins drive. The pubs and restaurants are great too! The plunge into the icy river every morning was a ye eat way to start the day! Couldn’t recommend high enough, Jenny was friendly and made us feel very welcome!
Superhost

Home in Henley-on-Thames

4.75 out of 5 average rating, 146 reviews

Cottage in Henley On Thames

SarahRating, 5 stars5 months ago
We had a wonderful weekend staying in Dawn’s beautiful cottage. Super clean, very well equipped, quiet & extremely comfortable. Stunning decor & wonderful outside space! Perfect location, just a two minute walk from Henley bridge. We can’t wait to return for a longer stay!
Superhost

Chalet in Benson

4.91 out of 5 average rating, 276 reviews

Mizpah Ecolodge

CarolineRating, 5 stars3 weeks ago
We had a lovely 4 nights here over New Year, with a very energetic pup who struggles a bit with outside noises. This cottage was perfect for us - I was worried that bc of it' location we would have people walking back and forth past it but once there you can see how the position of it allows it to feel completely private... in the 5 days we were there we did not see a single person unless we were out on one of the many stunning walks in the area. Tim has enclosed fields right next to the property which we were given the code for and were allowed to access whenever we wanted to let the pup have a run (early morning and nights ) very handy and made all the difference. The little towns were close and convinent if we needed to grab the odd item here and there . On arrival Paulina had a welcome tray for us in the kitchen with some lovely fruit cake, chocolates and biscuits, with some milk ready for our arrival in the fridge. I can highly recommend this property! Thk you Tim & Paulina.
Superhost

Guesthouse in Buckinghamshire

4.88 out of 5 average rating, 145 reviews

The Old Hay Barn, Ashley Green

FrancisRating, 5 stars4 weeks ago
We stayed over Christmas and loved the barn. It is spacious, well appointed and has a very comfortable bed. There was a lovely and plentiful selection of breakfast items. Jamie and Chrissie were both welcoming, friendly and helpful. We would definitely stay again and recommend it unreservedly.

Family-friendly home rentals with a pool

Superhost

Guesthouse in Tadley

4.75 out of 5 average rating, 25 reviews

DOG FRIENDLY COTTAGE

Ros & LizRating, 5 stars44 months ago
This was a great find. The conversion has created a great space to live in, huge bedrooms, 2 super bathrroms, large kitcehn with everything in it you require, and a large living - diningroom. To use and enoy the pool ensure the suns out! Highly reccomend it and would go back for longer another time.
Superhost

Home in tadley

4.78 out of 5 average rating, 23 reviews

Stunning hideaway house

AidanRating, 5 stars18 months ago
booked with miranda for a couple of nights and she couldn't have been a better host.. very helpful and responded to right awa to any queries I had.. the house and garden were both beautiful and the whole stay was very enjoyable.. would definaltet recommend 👌.
Superhost

Cottage in Wolverton Common

4.87 out of 5 average rating, 47 reviews

The Cottage, dog friendly,swimming pool in summer

OliverRating, 5 stars30 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.

Home in Cookham

5 out of 5 average rating, 34 reviews

Country House, 5bed, large garden, heated pool

DamionRating, 5 stars4 weeks ago
Just had a fantastic Christmas break in Dan’s house. Perfect home from home, beautifully decorated for Christmas with a real tree! Thanks so much, Dan. We loved staying in your house and had a fab time.
Guest favorite

Farm stay in Guildford

4.98 out of 5 average rating, 123 reviews

The Luxury Cottage

CathrineRating, 5 stars1 week ago
The place is in a farm, easy to find. The host is friendly and gave us clear instructions. All the rooms were very clean and well furnished. We also liked the art of the furniture which is unique and well maintained. It’s a good place to go with children for a quiet weekend outing. The place is well maintained too and the Host is responsive . I will be happy to visit again in summer.
Superhost

Home in Oxfordshire

4.88 out of 5 average rating, 221 reviews

Barn conversion, Henley-on-Thames

MartinRating, 5 stars3 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 .

Home in Wargrave

5 out of 5 average rating, 7 reviews

4 Bedroom Family Home with pool

LukeRating, 5 stars80 months ago
Lovely comfortable and spacious family house . Suzie the host was very friendly and obliging and made us feel very welcome in her beautiful home. Would definitely book again .

Quick stats about vacation rentals that are family-friendly in Maidenhead

  • Total rentals

    120 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    120 properties include access to wifi

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