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Vacation rentals with a pool in Windsor and Maidenhead

Find and book unique homes with a pool on Airbnb

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 favorite
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
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 favorite
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
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!***

Guest favorite
A scenic view showcases a lush green landscape surrounded by manicured hedges and diverse trees. Autumn colors are visible in the foliage, with muted yellows and greens punctuating the vast space. The cloudy sky creates a tranquil atmosphere over the serene setting.
Barn
4.95 out of 5 average rating, 131 reviews

Delightful one bedroom barn with beautiful views

Our beautiful rustic one bedroom barn is attached to the end of our family home. Situated in the popular Surrey Hills an area of outstanding beauty surrounded by many local award winning pubs and immediate access to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making Autumn and winter particularly lovely with board games available. Guests are also welcome to use the house facilities which include a heated swimming pool and tennis court.

Top guest favorite
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
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 favorite
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
4.93 out of 5 average rating, 150 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

Top guest favorite
A modern guest lodge is showcased, featuring a distinctive curved roof and large glass windows that enhance the natural light. The surrounding outdoor area is paved, including a pool with a cover and seating arrangements for relaxation.
Place to stay
4.99 out of 5 average rating, 103 reviews

The Pool House (for 2 Adults & 2 Children)

This unique, Architect designed self contained building, has a style all of its own. With an open plan kitchenette and island unit, including an oven, microwave, hob and fridge freezer, you can dine in or go out to the Market Town of Petersfield. The lounge area has a 72" TV with a full sky package and spare HDMI leads. There is a walk in shower wet room and a separate cloakroom. The bedroom is cosy, with a king size bed. There is a separate area with bunkbeds, for smaller children.

Superhost
The cottage is surrounded by lush greenery and a well-maintained garden. A gravel path leads to the entrance, framed by neatly trimmed hedges. Large windows reflect natural light, while bicycles are casually positioned nearby, suggesting an inviting outdoor environment.
Cottage
4.93 out of 5 average rating, 204 reviews

Beautiful S.Downs Cottage, pool and tennis

A private gate takes you directly onto the South Downs with some lovely foot and cycle paths on your doorstep. Close to the beach and city, Chichester, Portsmouth, Southhampton, Winchester, Goodwood and Witterings beaches are in easy reach while Liphook station takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. The pool and tennis court are available from May to end Sept/early Oct, Mon- Sat 9am - 1 pm.

Top guest favorite
A spacious bedroom features a comfortable bed dressed in light bedding. Large windows allow natural light to fill the room, with views of greenery outside. Artwork adorns the walls, and a cozy sitting area includes a chair and a television, enhancing the room's inviting atmosphere.
Guesthouse
4.96 out of 5 average rating, 163 reviews

Comfortable 1-Bedroom Guest Suite in rural setting

Quietly situated on the side of Blackdown in the South Downs National Park, 2 miles from Haslemere and convenient for visiting Chichester and Goodwood, The Barn is a well-appointed guest suite which offers comfortable accommodation for two. Convenient for exploring the local area, with immediate access to numerous public footpaths including the Sussex Border Path and Blackdown Hill. Ideally situated for animal lovers with an abundance of wildlife plus our own pet alpacas.

Guest favorite
The eco-friendly guest house is featured with a wooden facade, reflecting the blue sky. The view showcases a serene swimming pool, bordered by landscaped greenery, offering a tranquil outdoor space for relaxation.
Home
4.91 out of 5 average rating, 215 reviews

Cosy wood burner country views cold water swimming

Unique eco sustainable guest house built in 2022 with stunning views over private fields lined with Oak Trees as well as views overlooking a private new pristine 17m swimming pool. The pool is maintained Oct-Mar for cold water swimming. Quiet location, country walks (close to National Park) and a local pub 1 mile away. Modern, new stylish interiors with a cosy wood burner and large patio and fire pit outside. Conveniently located 15 miles to Gatwick Airport.

Top guest favorite
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
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.

Top guest favorite
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
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.

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.

Popular amenities for Windsor and Maidenhead rentals with a pool

When is the best time to visit Windsor and Maidenhead?

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Avg. price€ 155€ 272€ 174€ 262€ 430€ 252€ 140€ 181€ 446€ 194€ 197€ 399
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Quick stats about vacation rentals with a pool in Windsor and Maidenhead

  • Total vacation rentals

    Explore 60 vacation rentals in Windsor and Maidenhead

  • Nightly prices starting at

    Windsor and Maidenhead vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Windsor and Maidenhead vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor and Maidenhead rentals

  • 4.7 Average rating

    Windsor and Maidenhead stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Windsor and Maidenhead's top spots, include Ascot Racecourse, Virginia Water Lake, and Odeon Maidenhead

Destinations to explore