Vacation rentals with a pool in Windsor

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Top-rated rentals with a pool in Windsor

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

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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, 80 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, 57 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

Guest favorite
A comfortable lounge area features a spacious sectional sofa accented with decorative pillows. A round, metallic coffee table sits on a patterned rug, highlighting the warm wood floor. Natural light filters through the window, illuminating the green walls and indoor plant.
Home in Old Woking
4.92 out of 5 average rating, 12 reviews

Modern Escape-Jacuzzi & Ice Bath

Relax and unwind in our superbly located home with Spa Facilities. Inside you’ll find a fully-equipped kitchen that flows into an airy lounge and dining area. A garden at the back with hot & cold spas. Upstairs there's two spacious double bedrooms (one being a sofa bed), alongside a smaller child room and cot. Close to Woking Station, we're a short drive from Horsell Common and the River Wey with beautiful walks, great local food & entertainment. Suitable for 4 adults & one child/cot

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, 57 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.

Top guest favorite
A charming brick building is surrounded by lush greenery and vibrant trees, with scattered clouds above. The landscaped garden features blooming flowers, providing a serene backdrop for the property. A gravel driveway leads to the entrance, emphasizing the private and tranquil setting.
Condo in Oxfordshire
4.95 out of 5 average rating, 57 reviews

Henley apartment with heated pool

Four Star rated first floor apartment in its own self-contained block with heated outdoor swimming pool in an area of outstanding natural beauty. While secluded and peaceful, it’s within easy level walking distance of Henley-on-Thames and its famous stretch of river. The property is ideal for couples or up to 3 guests. In the summer our wonderful HEATED (new for 2025) swimming pool is available to our guests. If you would like exclusive use of the pool please ask at no extra cost.

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.

Superhost
A cozy living space features a dark sofa paired with a round wooden coffee table, illuminated by soft lighting. A dining area with a round table and green chairs is present, alongside glass doors that open to a green outdoor space, creating a welcoming atmosphere.
Home in Berkshire
5 out of 5 average rating, 3 reviews

Wellness Escape by River: Sauna, Pool, Hot Tub

Welcome to your ultimate riverside retreat! - Two cozy bedrooms and a single bathroom create an intimate escape. - The open-plan living space is perfect for unwinding with loved ones. - Enjoy a private sauna, hot tub, and cold plunge pool for ultimate relaxation. - Stunning river views from the master bedroom enhance tranquility. - A nearby utility room adds convenience with laundry facilities. - This stunning two-bedroom haven blends natural beauty with serene comfort.

Guest favorite
A sunlit terrace is showcased, featuring a table with two chairs and potted plants. A rustic wooden chair with a cozy throw is positioned nearby, offering a relaxing spot. Lush greenery surrounds the area, complementing the vibrant blue door in the background.
Guesthouse in Surrey
4.96 out of 5 average rating, 26 reviews

Island Hideaway on the Thames

APOLOGIES: The Hideaway is not available during 2025. Please search for "Idyllic House on the Thames" for alternative accommodation on the Island. --------------------- A cosy escape for all seasons, the Hideaway is a self-contained 1 bedroom home in a converted hayloft on an Island in the Thames. Perfectly arranged for couples, or easily adapted to accommodate small families with one child. Experience a truly unique lifestyle on an Island in the Thames.

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, 141 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.

Popular amenities for Windsor rentals with a pool

Quick stats about vacation rentals with a pool in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$100,161 GYD per night before taxes and fees

  • Verified guest reviews

    Over 30 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.8 Average rating

    Windsor stays are highly rated by guests—averaging 4.8 out of 5!

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