Family-friendly vacation rentals in Windsor and Maidenhead

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Popular amenities for Windsor and Maidenhead family-friendly rentals

Family-friendly home rentals with a hot tub

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

Spacious 2BR Retreat w/ Jacuzzi and Garden!

SafaRating, 5 stars5 days 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!
Condo in Raynes Park
4.78 out of 5 average rating, 9 reviews

Stunning 3B2Ba Huge entertaining space and hottub!

BrunaRating, 5 stars6 months ago
Great place and great host
Top guest favorite
Apartment 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.
Apartment 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.
Top guest favorite
Condo 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!
Top guest favorite
Cottage in Baughurst
4.96 out of 5 average rating, 369 reviews

Luxury rural thatched cottage with cedar hot tub.

ZoeRating, 5 stars1 week ago
Wow - Beautiful and tranquil place to stay with absolutely stunning gardens. Perfect place to stay to purely relax with the enjoyment of a private hot tub to use throughout , firepit and loungers in the gardens to use. Our dog loved this place and had so much to explore , the house supplies dog treats / and a dog bed , all the little touches were all noticed to make our stay as comfortable as possible! Keith / Jean were very communicative, and helpful during check in. The beds were very comfortable, each room pristine and decorated to a high standard , even provide slip on shoes and gowns to access the hot tub which was really handy! the continental breakfast supplied was lovely . We would love to come back and stay again , would recommend to anyone it is pure bliss, inside and outside , thank you!
Superhost
Apartment in Earl's Court
4.82 out of 5 average rating, 49 reviews

Large 2-Bedroom Apartment in Chelsea

GuyRating, 5 stars9 months ago
The apartment was great. The end bedroom gets some traffic noise but earplugs fixes this. The stairs, though many, were not an issue and we saw it as part of our exercise regime! A great experience all round. Perfectly placed and the private park was delightful.
Condo in Camden
4.94 out of 5 average rating, 16 reviews

Beautiful, modern flat, terrace, private parking

EmanueleRating, 5 stars1 week ago
Great place in a great location and great host. Very clean place, we really felt home! I definitely recommend it

Family- and pet-friendly home rentals

Top guest favorite
Apartment in Pamber Green
4.92 out of 5 average rating, 143 reviews

Self Contained Annex

CatrionaRating, 5 stars2 months ago
Beautiful home and a lovely stay. It was spotlessly clean with all the amenities provided, TV with various subscriptions, a cosy bedroom and access to the garden and fields. Very good communication with the hosts and easy check in. A lovely touch was fresh eggs provided and milk in the fridge to help myself to. I was cycling and this was a perfect country stay to rest and recover. 5* :)
Guest favorite
Guesthouse in Surrey
4.95 out of 5 average rating, 139 reviews

Separate guest suite Esher/Cobham area

MaryRating, 5 stars2 months ago
We enjoyed our 12 day stay at Linda's. We were well prepared in advance, and everything involved in getting checked in went very smoothly. We were very comfortable and slept well. Linda and her husband were friendly and helped us get oriented locally. The kitchen worked out extremely well for us to prepare most of our meals, and that helped us with some dietary issues. We would highly recommend Linda's place. It is a great balance between a quiet country place, yet close to shopping and restaurants in Cobham and Esher. We hope to be back again!
Superhost
Home in Crondall
4.84 out of 5 average rating, 122 reviews

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

AlanRating, 5 stars1 month ago
Perfect place to stay in lovely peaceful surroundings, lovely walks into the village with a couple of pubs, Toby and Maddy were super helpful and friendly and made us feel at home, Coach House was presented very well and exactly as described, wouldn’t hesitate to recommend.
Guest favorite
Guesthouse in Surrey
4.94 out of 5 average rating, 238 reviews

14th Century Dairy

FionaRating, 5 stars5 days ago
The Dairy is in a peaceful, idyllic part of rural Surrey. It had everything we needed, Beth was quick in her responses and we enjoyed our time there. We were only there for two nights but wish it had been much longer. We have already booked to return later in the summer.
Guest favorite
Cottage in Ibworth
4.94 out of 5 average rating, 175 reviews

Self contained, rural cottage, 2 double bedrooms

HannahRating, 5 stars3 weeks 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!
Superhost
Apartment in Hampton Wick
4.78 out of 5 average rating, 144 reviews

2 bed flat - SW London with parking

DanRating, 5 stars1 month ago
Hannah was attentive to our last minute needs. Apartment is in a great location next to the park and walking distance of Kingston town Center.
Guest favorite
Chalet in Benson
4.91 out of 5 average rating, 281 reviews

Mizpah Ecolodge

GerardRating, 5 stars3 weeks 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.
Superhost
Guesthouse in Buckinghamshire
4.88 out of 5 average rating, 153 reviews

The Old Hay Barn, Ashley Green

BaileyRating, 5 stars1 month ago
Brilliant location, homely feel and a host that couldn’t have provided for us. From a complimentary breakfast selection of pasty’s, eggs and cereals to a written booklet of places to eat / drink / party in the evening only in a less then 10 minute taxi drive away. Beautiful surrounding scenery with friendly local pubs… Can’t recommend enough.

Family-friendly home rentals with a pool

Superhost
Cottage in Wolverton Common
4.87 out of 5 average rating, 47 reviews

The Cottage, dog friendly,swimming pool in summer

OliverRating, 5 stars35 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
Condo in Wandsworth
4.85 out of 5 average rating, 415 reviews

Luxury Battersea studio w open fire, close to Park

LaurenRating, 5 stars3 days ago
Great Neighborhood to stay in. Walkable to Battersea park and many bus stops. Easy access to the flat. The only knock was that the flat upstairs from Charle’s place had ongoing construction and the construction worker smoked. Though, this was at no fault of the air bnb host. I had a lovely stay and enjoyed the Thai restaurant downstairs. Would stay in this cozy flat again.
Home in Cookham
5 out of 5 average rating, 34 reviews

Country House, 5bed, large garden, heated pool

DamionRating, 5 stars5 months 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.
Top guest favorite
Cottage in Buckinghamshire
4.97 out of 5 average rating, 353 reviews

Family friendly - rural, detached, home from home

CatherineRating, 5 stars1 week ago
Karen is a super friendly and responsive host, we felt very much welcomed and that our comfort and enjoyment of our stay was her priority. The cottage is stunning set in extensive grounds with its own private garden. We had everything we needed for an amazing, relaxing weekend with walks on our doorstep and the Ridgeway close by. One of the best places we have every stayed in, we hope to come back soon!
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 225 reviews

Barn conversion, Henley-on-Thames

JaneRating, 5 stars1 month ago
Thank you for another wonderful stay. We loved it the first time and the second time equally. Very friendly and welcoming hosts who go the extra mile! Thank you.
Superhost
Apartment in Norland
4.74 out of 5 average rating, 42 reviews

Garden Flat. Great for Transport & Sightseeing

EliasRating, 5 stars3 days ago
Want a nice quiet spot in West London that's affordable? This is it. Always got peaceful nights sleep and it's easy to get to the underground or walks to Shepherd's Bush.
Guest favorite
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.
Guest favorite
Apartment in Village
4.86 out of 5 average rating, 66 reviews

Wimbledon studio 350 m from Tennis

JudithRating, 5 stars9 months ago
Warm and friendly, accommodating hostess . Very comfortable accommodation beautifully situated for walking into glorious local village and access to transport all over London.

Quick stats about vacation 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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