
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.

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!***

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.

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

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 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.

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.

South Wing of Country House
Kick back and relax in this calm, stylish space. Only 35 mins by train from Central London, 8 miles from Heathrow. A small country estate with stunning gardens and 15 acres of land. Secure off street parking. Plenty of tourist attractions in locality, plus easy access to UK motorways for trips further afield. Pool, Jacuzzi and sauna are for your sole use and available between 9a.m - 12 noon, and 4 - 8.30p.m.

Narnia Inspired Mr Tumnus Cave
Step through the wardrobe and into a world of enchantment. Inspired by Mr Tumnus’s home and the timeless magic of Narnia, this immersive hideaway is brought to life by professional set designers and a member of The Magic Circle. Inside, you’ll find hidden secrets, bespoke magical props, and moments of wonder around every corner — all set within a cosy, stone-walled cave beneath the grounds of a Victorian house.
Popular amenities for Windsor and Maidenhead rentals with a pool
House rentals with a pool

The Mill House

Ivy | Ellerton Road | Pro-Managed

Spacious Home Heated Pool(May-Sep) in Tilehurst

The Place: Getaway

Stunning hideaway house

Modern Escape-Jacuzzi & Ice Bath

Cosy Cottage-House

Chic Family Home near Notting Hill
Condo rentals with a pool

Luxe 2BR/Paddington/Hyde Park

Private apartment - over garden quiet central

Hampstead Luxury Apartment- Opulent Split Level

Large apartment - pool & gym next door - HYDE PARK

Modern 2-bedroom flat with spa in historic Surrey

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

3 Bedroom Vault

2 Bedroom apartment. (Pics to be updated)
Other vacation rentals with a pool

Country House, 5bed, large garden, heated pool

One bedroom loft apartment

Wildflower shepherds hut - organic farm & vineyard

Beautiful one bed apartment on premises.

Forest Getaway - Country Retreat near Windsor

Family Friendly Country House - Pool & tennis

Surrey Cottage with indoor heated swimming pool

The Pool House
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 | G$37,646 GYD | G$66,089 GYD | G$42,247 GYD | G$63,789 GYD | G$104,571 GYD | G$61,279 GYD | G$102,062 GYD | G$112,101 GYD | G$80,311 GYD | G$38,691 GYD | G$47,894 GYD | G$97,042 GYD |
| 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 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$2,091 GYD 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
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- Rentals with pools Berkshire
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- Rentals with pools United Kingdom
- Tower Bridge
- London Bridge
- Big Ben
- Westminster Abbey
- British Museum
- Covent Garden
- Buckingham Palace
- Trafalgar Square
- Hampstead Heath
- The O2
- St Pancras International
- St. Paul's Cathedral
- Wembley Stadium
- Emirates Stadium
- ExCeL London
- Camden Market
- London Stadium
- Clapham Common
- Alexandra Palace
- Goodwood Motor Circuit
- Oxford University
- Blenheim Palace
- Primrose Hill
- Queen Elizabeth Olympic Park, London




