
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.

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!***

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

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.

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

Spacious Home Heated Pool(May-Sep) in Tilehurst

Bright spacious home with natural swimming pond

Ingleby Retreat

Country House, 4 Acres, Views & Swimming Pool

Entire guest suite in Marcham

The Place: 2-Bedroom Getaway

Cozy Studio with Private En-Suite, Kitchenette

Modern Escape-Jacuzzi & Ice Bath
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

Luxury retreat with extensive leisure facilities

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

3 Bedroom Vault
Other vacation rentals with a pool

The Party Barn

Christmas Pie Barns - Hot Tub and Treatment Room

The Green Escape - Private Cabin Retreat in London

Grayswood Cowshed in stunning Grounds

Four Bed House with Drive. Pool & Gym minutes away

A Romantic Escape in a Traditional Wooden Cabin

An amazing flat in Chelsea!

Barn conversion, Henley-on-Thames
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 € 9 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
- British Museum
- Covent Garden
- Buckingham Palace
- Big Ben
- Trafalgar Square
- Tower Bridge
- Wembley Stadium
- The O2
- London Bridge
- Hampstead Heath
- Emirates Stadium
- St. Paul's Cathedral
- St Pancras International
- ExCeL London
- Camden Market
- London Stadium
- Alexandra Palace
- Clapham Common
- Oxford University
- Blenheim Palace
- Goodwood Motor Circuit
- Primrose Hill
- Queen Elizabeth Olympic Park, London
- Windsor Castle