Vacation rentals with a pool in Windsor and Maidenhead

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Top-rated rentals with a pool in Windsor and Maidenhead

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
A well-maintained garden features a stone pathway leading to the cottage, bordered by green lawns and vibrant red flowers. Various outdoor seating options are scattered throughout the area, with potted plants adding a charming touch. A distant shed is visible, complementing the serene landscape.
Cottage in Cuddington
4.96 out of 5 average rating, 163 reviews

Escape to Country Living at its Finest!

Escape to the country and unwind at this charming, elegant cottage in 2 acres of lovely gardens with swimming pool, tennis badminton and table tennis, and county walks starting from your door. Located on the edge of the award winning village of Cuddington, walk to the thatched roof pub for drinks and dinner or village store for supplies and news papers. Only 10 minutes drive to the bustling market town of Thame, 35 minutes to Oxford, 40 minutes to London by train and 45 minutes to London LHR.

Guest favourite
Home in Camden Town
4.77 out of 5 average rating, 112 reviews

Victorian cottage w/ Garden near Camden Mkt

Instead of renting a flat, with people above and below you, why not rent a private historical townhouse? Character-filled, 2-bedroom Victorian cottage with private walled garden, A/C, bbq, separate dryer -- all rare for London! Built in 1850 and located in a conservation area, yet with Famous Camden Market at the end of the street, it has great transport links - Direct train to Wimbledon nearby! There are kingsize and double beds and also a comfy double sofa bed, so can accommodate 6 people

Guest favourite
A warm dining area is presented with a wooden table set for a meal. Elegant glassware, a candle, and wine bottles complement a bouquet of roses. Exposed brick walls enhance the rustic charm, while shelves display a curated selection of decor items.
Condo in London
4.85 out of 5 average rating, 426 reviews

Luxury Battersea studio w open fire, close to Park

Stunning, cosy spacious open plan flat with under-heated hard wood floors, leather sofa and King Size double leather sleigh bed. This flat is on a main road above a great Thai restaurant, in a fantastic location walking distance from many bars, cafés, shops & Battersea Park, London's only park by the river. Vinyl record turntable, Netflix and Apple TV system, and 24hr check in. ***Please remember to book for the correct number of guests. If there are two of you, please ensure you book for 2!***

Top guest favourite
A clear blue swimming pool is framed by a spacious patio featuring sun loungers and wooden dining furniture. The dark wooden loft conversion is visible in the background, surrounded by leafy greenery and potted plants, creating a serene outdoor atmosphere.
Barn in Loxwood
4.99 out of 5 average rating, 162 reviews

Country getaway on rural Surrey/Sussex border.

Redwood is a charming loft conversion with views overlooking a garden, swimming pool, and farmland fields in the perfect location for both the South Downs and the Surrey Hills Area of Outstanding Natural Beauty, with several nearby pubs. Situated within the quaint village of Loxwood, you can enjoy the enchanting Surrey/Sussex countryside and rich wildlife. Enjoy a drink as the sun sets over our swimming pool or a picnic looking over the stunning nearby views. Continental Breakfast included.

Top guest favourite
An indoor swimming pool is highlighted with a clear blue surface, surrounded by warm wooden paneling. Skylights allow natural light to fill the space, while a hot tub sits to one side. Large windows offer views of the surrounding greenery.
Cottage in Surrey
4.93 out of 5 average rating, 149 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

The cottage is situated on a private estate with complete solitude in 15 acres of orchards and fields. Guests are able to use our indoor swimming pool and hot tub at no charge. This is on the left of our family house 2 minutes walk from the cottage The 2 floor cottage has recently been fully renovated and you will find it to be warm, welcoming and decorated and furnished beautifully with full SKY TV, SKY Movies and Netflix available. Our family home is very close by if you need us

Guest favourite
A comfortable lounge area is furnished with a brown leather sofa, two blue armchairs, and a wooden coffee table. Decor includes woven rugs and decorative baskets. A large television is positioned against the wall, with light streaming in through French doors.
Farm stay in Guildford
4.97 out of 5 average rating, 146 reviews

The Luxury Cottage

Whitmoor Farm, Whitmoor Lane, GU47QB is in the heart of Surrey. The accommodation offers 2 bedrooms both with double beds and bunk beds. A lounge with Sky TV, WIFI internet. Tennis court, trampoline and swimming pool. The swimming pool is a communal pool, heated from 1 May to 30 September and remains open for use until 15 October. The property is set on 38 Acres of land and woodlands between the Historic Town of Guildford and Woking with fast train access to London.

Top guest favourite
An outdoor seating area features a circular table surrounded by dark wooden chairs. A barbeque grill stands nearby, and the surrounding garden is lush with greenery. The unique architecture of the property includes charming brick walls and vibrant green doors, framed by foliage.
Cottage in Chobham
4.99 out of 5 average rating, 132 reviews

The Coach House

The Coach House is a totally unique property, nestled in the peaceful surroundings of Chobham Common. Spread over two floors, this charming accommodation offers 2 bedrooms, 2 bathrooms, a sitting room, a dining room, a kitchen, & a utility room. There is also an outdoor seating area equipped with barbeque, perfect for unwinding. The quirky design & characterful features of this historic building add to its charm & make it a truly delightful place to stay.

Guest favourite
A panoramic view of the city skyline is visible through an open window. City lights twinkle against the night sky, with distant buildings illuminated in various colors. The atmosphere is calm, showcasing the expansive urban landscape from a top-floor vantage point.
Condo in Canning Town North
4.94 out of 5 average rating, 107 reviews

Unique 1-bd penthouse 3 minutes walk to Excel/o2

This unique place is ideal for business or family trips Highly exclusive one bedroom apartment at Royal Victoria just 2 mins walk to ExCel Conference Center, 15 mins away from Canary Wharf and cable car ride from O2 Arena, DLR station literally 1 min away taiing you to the city and tower gateway in just 14minutes, Elisabeth Line 3 mins walking distance. The place benefits 24h concierge service and private gym, with 24h private security throughout the area.

Top guest favourite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guesthouse in Garsington
4.94 out of 5 average rating, 465 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Top guest favourite
The spacious outdoor area features a serene swimming pool surrounded by artificial grass. A hot tub and loungers are visible beside the pool, with a patio table and chairs positioned nearby. The charming chalet stands in the background, showcasing large glass doors.
Farm stay in Henton
4.93 out of 5 average rating, 140 reviews

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

Enjoy the tranquillity and seclusion of our spacious pool house chalet, complete with private seasonally heated (1 May to 30 September) outdoor swimming pool and all year round hot tub Jacuzzi spa, located on our 30 acre farm and equestrian centre in the rural hamlet of Henton on the outskirts of Chinnor, Oxfordshire. The Pool House is an ideal location for couples, families, walkers, cyclists, coarse/carp anglers and business travellers.

Superhost
The image showcases a large rooftop pool surrounded by modern buildings, featuring a spacious sun deck with lounge chairs. Crystal-clear water reflects the blue sky, while landscaped areas with palm trees add greenery to the scene.
Apartment in Nine Elms
4.81 out of 5 average rating, 149 reviews

Stunning 1 Bed in Battersea w/ Pool, Gym & Rooftop

Urban Rest Battersea offers luxury 1–3 bedroom apartments in a prime riverside location. Enjoy hotel-style amenities like rooftop pool, sky lounges, gyms, co-working spaces, and a pet spa. Each apartment features modern design, smart home tech, floor-to-ceiling windows, private balconies, and high-end appliances. Located near Battersea Power Station, Nine Elms provides vibrant shopping, dining, and fast city connections amid green spaces.

Guest favourite
A wooden decked garden area features a dining table set with a red and white tablecloth. Four metal chairs surround the table, which is adorned with bowls and containers of various food items. Lush greenery and low plants create a serene environment.
Apartment in Hackney
4.81 out of 5 average rating, 152 reviews

Spacious Designer Garden Flat in Hackney

Stay in this oasis in the most sought after location in Hackney - London Fields, just minutes away from Central London! Home to artist, Ali Pretty, this is a beautifully designed large ground floor flat featuring glass doors that open out into a huge decked garden. It has a luxurious bedroom with a super kingsize bed, a spacious open plan reception area, a well equipped kitchen. There’s an amazing bakery and lots of shops close by.

Popular amenities for Windsor and Maidenhead rentals with a pool

Quick stats about vacation rentals with a pool in Windsor and Maidenhead

  • Total rentals

    60 properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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