
Holiday 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.

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.

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!***

An amazing flat in Chelsea!
A spacious 1-bed Manhattan style flat in the prestigious development, Chelsea Creek. Finished to an excellent standard, the property has a double bedroom with fitted storage and a modern bathroom. The kitchen is contemporary and fully equipped and open plan with the reception area. The property is walking distance to Fulham Broadway underground or directly next to Imperial Wharf over ground station. There is also access to gym and spa for long staying guests only (= 12 NIGHTS MINIMUM)

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

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.

2BR Victorian cottage w/ Garden near Camden Mkt
Instead of renting a flat, with people above and below you, why not rent a private Victorian townhouse? Character-filled, 2-bedroom cottage with private walled garden, eco-fireplace, A/C, bbq, separate dryer -- all rare for London! Built in 1850 and located in a quiet conservation area, yet with Famous Camden Market at the end of the street, it has great transport links. There are uk kingsize and queen beds and also a comfy queen sofa bed, so can accommodate 6 people

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.

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.

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.

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.

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
House rentals with a pool

Spacious Home Heated Pool(April-Sep) in Tilehurst

Bright spacious home with natural swimming pond

Pool & Piano | Hidden Oasis in Kensington Olympia

Wellness Escape by River: Sauna, Pool, Hot Tub

The Coach House

2 bedroom flat - 1 minute to station

Stunning hideaway house

Chic Family Home near Notting Hill
Condo rentals with a pool

Lovely Flat Zone 2 close to DLR

Hampstead Luxury Apartment- Opulent Split Level

Private apartment - over garden quiet central

Large apartment - pool & gym next door - HYDE PARK

Battersea Power Station | River View | 2BR 2BA

Soho House Luxury large 1 bd Gym/Pool/Cinema/

3 Bedroom Vault

West Brompton, AC , air con, 1 BR Apart
Other holiday rentals with a pool

The Green Escape - Private Cabin Retreat in London

Chiswick studio garden Pool house

Cosy Coach House near Henley & Marlow

One bedroom loft apartment

Barn conversion, Henley-on-Thames

Narnia Inspired Mr Tumnus Cave

Forest Getaway - Country Retreat near Windsor

Chez Florence flat in Huf Haus with heated pool
When is the best time to visit Windsor and Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $268 AUD | $471 AUD | $301 AUD | $455 AUD | $745 AUD | $437 AUD | $728 AUD | $799 AUD | $572 AUD | $276 AUD | $341 AUD | $692 AUD |
| Avg. temp | 6°C | 6°C | 8°C | 11°C | 14°C | 17°C | 19°C | 19°C | 16°C | 12°C | 8°C | 6°C |
Quick stats about holiday rentals with a pool in Windsor and Maidenhead

Total holiday rentals
Explore 60 holiday rentals in Windsor and Maidenhead

Nightly prices starting at
Windsor and Maidenhead holiday rentals start at $75 AUD per night before taxes and fees

Verified guest reviews
Over 1,730 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Windsor and Maidenhead holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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- Rentals with pools Berkshire
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- Rentals with pools United Kingdom
- Tower Bridge
- Big Ben
- Paddington
- British Museum
- Natural History Museum
- Covent Garden
- London Bridge
- Marble Arch
- Tottenham Court Road
- Buckingham Palace
- Kings Cross
- Hampstead Heath
- The O2
- St Pancras International
- Piccadilly Theatre
- Trafalgar Square
- Battersea Power Station (disused)
- Emirates Stadium
- ExCeL London
- Royal Albert Hall
- Wembley Stadium
- Olympia Events
- Russell Square
- Borough Market




