
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.

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 barn with stunning outside swimming pool
Perfect for days spent exploring Henley on Thames and the Chiltern Hills Lazy days lounging beside the shared swimming pool with private outdoor seating area by pool Close to Henley on Thames with its many annual events... Henley Arts Trail - May Henley Royal Regatta - July Henley Festival - July Thames Traditional Boat Rally - July Rewind Festival - July Henley Literary Festival - September Christmas Festival - November .....and so much more to do and see in this fabulous Town.

The Cottage, Little Marlow
The Cottage is situated in the delightful village of Little Marlow with two friendly pubs which serve food and a 12th century church. It is set in a conservation area adjoining a nature reserve with a large lake and a footpath that leads you to the river Thames. The picturesque river towns of Marlow, Henley and Windsor are nearby and London is only half an hours train journey. Boats and paddle boards can be hired locally and the area is great for walking, cycling and bird watching.

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.

The Luxury Cottage – Surrey Countryside Retreat
The Luxury Cottage at Whitmoor Farm accommodates up to 8 guests with two bedrooms, each with a king bed and bunk beds, plus a lounge with Sky TV, Wi-Fi, and a fully equipped kitchen. Guests can enjoy the estate’s tennis court, trampoline, and shared outdoor swimming pool (heated May–Sept; open until 15 Oct). Set on 38 acres of woodlands between Guildford and Woking, with fast train access to London. Pets allowed — up to 2 small pets, £25 per pet for the stay.

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.

One bedroom apartment Mickleham, near Dorking
Separate entrance (via shared garden) separately lockable apartment (kitchen/living room, double bedroom + private bathroom) in Victorian farmhouse in a rural village between Leatherhead and Dorking, less than an hour from Wimbledon, central London & airports, 5 minutes from Denbies vineyard, 10 minutes from the M25, 15 minutes from Epsom races for the Derby. Hiking and mountain biking on Box Hill and in the Surrey Hills.

The Mill House
A stunning 4-bedroom Mill House set in the beautiful Oxfordshire countryside close to the city of Oxford, Blenheim Palace and Bicester Village. The house is set in a large garden with a swimming pool and tennis court. The house is within walking distance of the Crazy Bear Hotel and a short drive from the renowned Le Manoir aux Quat’Saisons. We are in an idyllic spot perfect for relaxing with friends or family.
Popular amenities for Windsor and Maidenhead rentals with a pool
House rentals with a pool

The Chiltern way - Annex w/ Kingsize Bed

Country House, 5bed, large garden, heated pool

Spacious Home Heated Pool(April-Sep) in Tilehurst

Pool & Piano | Hidden Oasis in Kensington Olympia

Barn conversion, Henley-on-Thames

Forest Getaway - Country Retreat near Windsor

Family Friendly Country House - Pool & tennis

Chic Family Home near Notting Hill
Condo rentals with a pool

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

2 Bedroom apartment. (Pics to be updated)

Contractor Friendly | FREE Secure Parking

1 Br Apartment Near Middlesex University London
Other vacation rentals with a pool

Spacious & stylish family home

Independent studio sleeps up to 1-4

Large Country House in stunning Hampshire Village

Modern 1-bed home with free parking

The Meadow, Bovingdon village, Herts/Bucks border

*Beautiful Modern Studio Flat; Professional Market

4/5 Bedroom Detached House, Heated Swimming Pool

Pool open! Private Retreat house + studio+garden.
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$37,633 GYD | G$66,066 GYD | G$42,232 GYD | G$63,766 GYD | G$104,535 GYD | G$61,258 GYD | G$102,026 GYD | G$112,062 GYD | G$80,283 GYD | G$38,678 GYD | G$47,877 GYD | G$97,009 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$10,454 GYD per night before taxes and fees

Verified guest reviews
Over 1,730 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
- Big Ben
- Paddington
- British Museum
- Natural History Museum
- Covent Garden
- London Bridge
- Marble Arch
- Tottenham Court Road
- Buckingham Palace
- Hampstead Heath
- Kings Cross
- St Pancras International
- The O2
- Piccadilly Theatre
- Trafalgar Square
- Battersea Power Station (disused)
- Emirates Stadium
- ExCeL London
- Wembley Stadium
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market




