
Holiday rentals with a pool in Windsor and Maidenhead
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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!***

Christmas Barn, private heated pool and 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.

Delightful one bedroom barn with beautiful views
Our beautiful rustic one bedroom barn is attached to the end of our family home. Situated in the popular Surrey Hills an area of outstanding beauty surrounded by many local award winning pubs and immediate access to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making Autumn and winter particularly lovely with board games available. Guests are also welcome to use the house facilities which include a heated swimming pool and tennis court.

Country getaway on rural Surrey/Sussex border.
Redwood is a charming loft conversion with views overlooking a garden, swimming pool, and farmland fields in the perfect location for both the South Downs and the Surrey Hills Area of Outstanding Natural Beauty, with several nearby pubs. Situated within the quaint village of Loxwood, you can enjoy the enchanting Surrey/Sussex countryside and rich wildlife. Enjoy a drink as the sun sets over our swimming pool or a picnic looking over the stunning nearby views. Continental Breakfast included.

Beautiful S.Downs Cottage, pool and tennis
A private gate takes you directly onto the South Downs with some lovely foot and cycle paths on your doorstep. Close to the beach and city, Chichester, Portsmouth, Southhampton, Winchester, Goodwood and Witterings beaches are in easy reach while Liphook station takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. The pool and tennis court are available from May to end Sept/early Oct, Mon- Sat 9am - 1 pm.

Comfortable 1-Bedroom Guest Suite in rural setting
Quietly situated on the side of Blackdown in the South Downs National Park, 2 miles from Haslemere and convenient for visiting Chichester and Goodwood, The Barn is a well-appointed guest suite which offers comfortable accommodation for two. Convenient for exploring the local area, with immediate access to numerous public footpaths including the Sussex Border Path and Blackdown Hill. Ideally situated for animal lovers with an abundance of wildlife plus our own pet alpacas.

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.

Stunning 2 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.
Popular amenities for Windsor and Maidenhead rentals with a pool
House rentals with a pool

The Mill House

Spacious Home Heated Pool(May-Sep) in Tilehurst

Ingleby Retreat! All-seasons escape

Entire guest suite in Marcham

Modern Escape-Jacuzzi & Ice Bath

Chic Family Home near Notting Hill

6BR House | Temple Fortune | Heated Pool & Parking

Eden Cottage, your home away
Condo rentals with a pool

Lovely Flat Zone 2 close to DLR

Private apartment - over garden quiet central

Large apartment - pool & gym next door - HYDE PARK

3 Bed Flat with Garden and Pool

Luxury retreat with extensive leisure facilities

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

3 Bedroom Vault

Cozy studio - O2, Greenwich Park & Thames River
Other holiday rentals with a pool

Shepherds hut - visit Ashdown Forest, Standen

Grayswood Cowshed in stunning Grounds

Four Bed House with Drive. Pool & Gym minutes away

The Nook at Yew Tree Cottage

An amazing flat in Chelsea!

The Barn at Holly Cottage. Indoor Pool and tennis

The Place: 2-Bedroom Getaway

Spacious 2 bed Designer flat in Notting Hill
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 | $275 AUD | $483 AUD | $309 AUD | $467 AUD | $765 AUD | $448 AUD | $747 AUD | $820 AUD | $588 AUD | $283 AUD | $350 AUD | $710 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 $15 AUD per night before taxes and fees

Verified guest reviews
Over 1,710 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
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- Rentals with pools Berkshire
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- Rentals with pools United Kingdom
- Tower Bridge
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