
Holiday rentals with a pool in Windsor and Maidenhead
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Top-rated rentals with a pool in Windsor and Maidenhead
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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.

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

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!***

Period barn, private heated swimming pool, hot tub
This magnificent country property, complete with an award winning heated pool complex is set high in the chiltern hills, bordering an area of outstanding natural beauty yet located only half a mile from the London Underground Met Line and Waitrose! Explore acres of orchards, formal and walled gardens, a lake, pergolas, and wild meadows, surrounded by ancient woodland and farmland. Escape to heaven in this spa like tranquil retreat. Leave your stress behind and visit this high tech masterpiece.

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

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

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.

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.

Cosy Coach House near Henley & Marlow
The Coach House is a stylish one bedroom studio overlooking a beautiful informal walled garden. In summer, guests are welcome to use the outside pool. There is also a BBQ & fire pit to enjoy. Situated near the beautiful villages of Wargrave, Twyford, Henley-On-Thames & Marlow, it is a perfect location for exploring the area or simply a lovely base to unwind. There are many lovely walks, activities & fabulous restaurants to explore as well as the River Thames.

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.

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.

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.
Popular amenities for Windsor and Maidenhead rentals with a pool
House rentals with a pool

The Mill House

Ivy | Ellerton Road | Pro-Managed

Spacious & stylish family home

Bright spacious home with natural swimming pond

Pool & Piano | Hidden Oasis in Kensington Olympia

Stunning hideaway house

Modern Escape-Jacuzzi & Ice Bath

Chic Family Home near Notting Hill
Condo rentals with a pool

Hampstead Luxury Apartment- Opulent Split Level

Luxury Central London Penthouse +£100 Dining Gift

Private apartment - over garden quiet central

Large apartment - pool & gym next door - HYDE PARK

Battersea Power Station | River View | 2BR 2BA

3 Bed Flat with Garden and Pool

Riverside Flat with Pool/Jacuzzi/Sauna

Soho House Luxury large 1 bd Gym/Pool/Cinema/
Other holiday rentals with a pool

Christmas Pie Barns - Hot Tub and Treatment Room

Country House, 5bed, large garden, heated pool

A Romantic Escape in a Traditional Wooden Cabin

Barn conversion, Henley-on-Thames

Old Wharf Cottage

Forest Getaway - Country Retreat near Windsor

Chez Florence flat in Huf Haus with heated pool

Luxurious 5 beds house 20 min from Central London
Quick stats about holiday rentals with a pool in Windsor and Maidenhead
Total rentals
60 properties
Nightly prices starting at
$15 AUD 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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- British Museum
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- Big Ben
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- Tower Bridge
- London Bridge
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