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.

%{current} / %{total}1 / 1
Top guest favorite
The floating home features a green rooftop adorned with lounge chairs and a patterned rug. A wooden deck extends towards the water, while a hot tub is visible on an adjacent patio. A small boat rests alongside the structure, surrounded by greenery.
Island in Hampton
5 out of 5 average rating, 79 reviews

Tulana Taggs - floating home on idyllic island

Relax in this unusual setting of a floating home on the inner lagoon of Taggs Island situated on the river Thames, close to Hampton Court Palace, Richmond & Kingston. Tulana offers guests a singular experience of living in urban nature in London. A brand-new floating home completed May 2022, as featured on the Channel 4's 'My Floating Home' in August 2023. Come and slow down at Tulana, immerse yourself in a bit of luxury & enjoy the best of both worlds - London sights & communing with nature.

Top guest favorite
The exterior of a converted barn is visible, showcasing a rustic structure with a clock tower. Large windows framed in wood offer glimpses of the welcoming interior. Well-maintained greenery and flower beds surround a gravel courtyard, creating a tranquil outdoor space.
Barn in Henley-on-Thames
4.98 out of 5 average rating, 56 reviews

Two Bed Large Countryside Barn with Indoor Pool

‘The Clock Tower ’- is a unique and stylish converted barn with oak beams and high ceilings. This 2 bed (2 bath) is cosy and full of charm in the heart of the countryside, close to Henley-on-Thames. Indoor pool. Sleeps 4 (2 Large Doubles) Stunning views, beautiful walks, great pubs, restaurants, and historic places to visit only a short stroll or distance away. An ideal getaway for a weekend or longer stay in the Oxfordshire countryside. Henley-on-Thames 6 miles, Reading station 6.5 miles

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 in Surrey
4.93 out of 5 average rating, 153 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 favorite
Cottage in Bix
4.91 out of 5 average rating, 11 reviews

Luxury barn with stunning outside swimming pool

Perfect for days spent exploring Henley on Thames and the Chiltern Hills Lazy days lounging beside the shared swimming pool with private outdoor seating area by pool Close to Henley on Thames with its many annual events... Henley Arts Trail - May Henley Royal Regatta - July Henley Festival - July Thames Traditional Boat Rally - July Rewind Festival - July Henley Literary Festival - September Christmas Festival - November .....and so much more to do and see in this fabulous Town.

Superhost
The cottage features a traditional brick exterior with a blue front door, surrounded by a natural landscape of trees and shrubs. A spacious area of lawn is visible in front, offering a sense of privacy and tranquility.
Cottage in Little Marlow
4.88 out of 5 average rating, 56 reviews

The Cottage, Little Marlow

The Cottage is situated in the delightful village of Little Marlow with two friendly pubs which serve food and a 12th century church. It is set in a conservation area adjoining a nature reserve with a large lake and a footpath that leads you to the river Thames. The picturesque river towns of Marlow, Henley and Windsor are nearby and London is only half an hours train journey. Boats and paddle boards can be hired locally and the area is great for walking, cycling and bird watching.

Superhost
An indoor pool features a striking wooden ceiling with exposed beams. The tiled area includes a hot tub and a spacious swimming pool, both surrounded by large windows that allow natural light to fill the space. Scenic wall murals enhance the relaxation atmosphere.
Condo in Buckinghamshire
4.87 out of 5 average rating, 101 reviews

Luxury retreat with extensive leisure facilities

An opportunity for a relaxed and luxurious break in a large comfortable apartment. With the exclusive use of a fantastic pool, hot tub, games room and tennis court. Towels, gowns and spa slippers are provided, and massage and beauty treatments are also available. Surrounded by 4 acres of gardens and woods for walks, BBQs and chilling out. Great for families too with lots of play areas for kids with a football pitch, large trampoline, swings, slide, climbing wall and treehouse.

Top guest favorite
Farm stay in Guildford
4.97 out of 5 average rating, 151 reviews

The Luxury Cottage – Surrey Countryside Retreat

The Luxury Cottage at Whitmoor Farm accommodates up to 8 guests with two bedrooms, each with a king bed and bunk beds, plus a lounge with Sky TV, Wi-Fi, and a fully equipped kitchen. Guests can enjoy the estate’s tennis court, trampoline, and shared outdoor swimming pool (heated May–Sept; open until 15 Oct). Set on 38 acres of woodlands between Guildford and Woking, with fast train access to London. Pets allowed — up to 2 small pets, £25 per pet for the stay.

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 in Chobham
4.99 out of 5 average rating, 140 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 in Garsington
4.94 out of 5 average rating, 489 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 favorite
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.

Guest favorite
A well-maintained garden area is visible, featuring a children's swing and a vibrant red British phone box. The surrounding greenery and fencing provide a private atmosphere, while a portion of the swimming pool can be seen to the right.
Farm stay in Mickleham
4.74 out of 5 average rating, 86 reviews

One bedroom apartment Mickleham, near Dorking

Separate entrance (via shared garden) separately lockable apartment (kitchen/living room, double bedroom + private bathroom) in Victorian farmhouse in a rural village between Leatherhead and Dorking, less than an hour from Wimbledon, central London & airports, 5 minutes from Denbies vineyard, 10 minutes from the M25, 15 minutes from Epsom races for the Derby. Hiking and mountain biking on Box Hill and in the Surrey Hills.

Top guest favorite
A charming Mill House, featuring a stone exterior and a spacious front entrance. Lush green grass and neatly trimmed hedges frame the property, while flowering lavender lines the pathway leading to the door. A second building is visible to the right, enhancing the picturesque setting.
Home in Stadhampton
4.98 out of 5 average rating, 55 reviews

The Mill House

A stunning 4-bedroom Mill House set in the beautiful Oxfordshire countryside close to the city of Oxford, Blenheim Palace and Bicester Village. The house is set in a large garden with a swimming pool and tennis court. The house is within walking distance of the Crazy Bear Hotel and a short drive from the renowned Le Manoir aux Quat’Saisons. We are in an idyllic spot perfect for relaxing with friends or family.

Popular amenities for Windsor and Maidenhead rentals with a pool

When is the best time to visit Windsor and Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,633 GYDG$66,066 GYDG$42,232 GYDG$63,766 GYDG$104,535 GYDG$61,258 GYDG$102,026 GYDG$112,062 GYDG$80,283 GYDG$38,678 GYDG$47,877 GYDG$97,009 GYD
Avg. temp6°C6°C8°C11°C14°C17°C19°C19°C16°C12°C8°C6°C

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 G$10,454 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,730 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