
Vacation rentals with a pool in City of Winchester
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Top-rated rentals with a pool in City of Winchester
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Popular amenities for City of Winchester rentals with a pool
House rentals with a pool

Discounted Ferries with Medina Rise Lodge
Lovely place, awesome view & location. Well equipped with everything you need inside. Very communicative and quickly answered any questions I had. Also made it so easy to book the ferry for us - thank you so much

Luxury 2 bdr lodge, dog friendly,close to Mudeford
Fabulous place to stay, had all we needed. Beautiful area of the country.

Coastal, New Forest 3 Bed Home Facilities Included
We stayed at Sam’s place to celebrate my husbands birthday. From the start Sam was responsive, friendly, answered questions and gave some fab advice. When I made a request she did everything she could to make it happen. The caravan itself is in a lovely peaceful part of the park with easy walking distance to the woods for the dog to have a run and also to the beach where we wandered to the pub and then back for an ice cream. Sam clearly explained how everything worked, where everything was & what she was doing to make things perfect for her guests. Her guide for things to do was really helpful so our days were filled and never dull. I would call this caravan a proper family home, it does everything it’s suppose to so you can just relax and enjoy your holiday. When I had some sad family news, Sam went out of her way to make sure we were ok and that we didn’t need to rush out the caravan on check out, so if you want a proper family home from home that does what it says - visit here! 🩷

Starfish Lodge Discounted ferry sailings available
We had the most wonderful stay at this lodge on the beautiful Isle of Wight. Tucked away in a peaceful caravan park just a stone’s throw from the sea, it offered the perfect mix of relaxation and seaside charm. The location couldn’t be better—waking up to the beautiful sea view and being able to stroll down to the beach in just minutes was absolute bliss. The on site pool and playground were the perfect end to a day exploring for our kids, all the staff here were friendly, helpful and couldn’t do enough to help. The accommodation itself was spotless, stylish, and incredibly comfortable. Everything we needed was there, from towels, a well-equipped kitchen to cozy beds and a lovely lounge area with the most stunning uninterrupted sea views . It felt more like a boutique coastal retreat than a lodge! Can’t recommend this place highly enough—whether you’re after a romantic escape, a quiet solo retreat, or a family break by the sea, this gem has it all. Thank you Rob :)

Rosie’s Isle of Wight Caravan - Whitecliff Bay
Our time in Rosie’s caravan was truly enjoyable. The space was spotless and well-organized, making it feel immediately welcoming. The shower had excellent pressure and consistently hot water, which was a real treat. We had no issues with the TV reception, and everything worked smoothly. The king-size bed was incredibly comfortable, complemented by soft, supportive pillows. The kitchen was impressively well-equipped—everything we needed was right at our fingertips. Rosie herself was a fantastic host—warm, quick to respond, and full of helpful local tips that really enhanced our trip. We will come back again!

Luxury Seafront Family Home - Indoor Pool
A beautiful house in a lovely location. Fresh air holidays were quick with all communications and very helpful when i had questions. This house had everything we needed and was fabulous for a family break for 9 of us

Eden Cottage, your home away
We had a lovely stay at Eden Cottage. The cottage had everything we needed with some thoughtful little extras in the kitchen and bathroom. Our little Frenchies sniffed their way around the enormous secure grounds and the pool was a real treat too! We checked out and drove just 30mins down to the coast and had a great walk in the sunshine watching all the kite surfers at Hayling Island followed by a giant ice cream! Thanks again Kevin & Debbie 😊 x

Incredible sea views and heated outdoor pool
The house is exactly as advertised. Spotlessly clean. The rooms are spacious. The whole house is very well maintained. The location is superb. Absolutely nothing to complain about. I would thoroughly recommend it. Our hosts were very easy to contact and made sure we knew everything and had everything.
Condo rentals with a pool

Beautiful 3-bed flat by the sea with use of pool
The property is absolutely immaculate. It is more spacious than the photos suggest. The beach is literally at the end of the drive. Such a convenient spot. And the beds!! Well, if you don’t sleep well here then you won’t sleep well anywhere. Great place. Great host. Great time.

Holiday apartment own heated indoor pool & sauna
Awesome location and full length swimming pool with Sauna. Only a 15 min walk into Swanage, beautiful castle only 10 min away and views of the sea. Fantastic full size swimming pool and sauna, our 8 and 10 year old loved it. We weren't able to use the snooker table due to the age of our kids and the lounge is not the most sociable set up for the evenings but the swimming pool made up for it ;-)

Luxury Penthouse: Spacious & Stylish
This air bnb is an amazing. I 100% recommend to anyone wanting to stay here. First of all the apartment is stunning, beautifully furnished with everything you could need. We stayed with two small children and it was very easy with enough space for the adults to relax in the evening. The location is peaceful with breathtaking views. On top of this it was spotless I could not fault anything. Our host Simon was incredibly helpful, quick to reply and always happy to help.

Luxury 2 Bedroom Apartment - New Forest
Wonderful, well appointed apartment over 2 floors. Large balcony with a lovely view. We shall definitely return if we can

Balcony On The Bay - FREE Car Ferry 3+ nights
We loved the apartment - it was spotless, spacious, and in the most gorgeous seafront location. Hosts had fab communication too. We love the area and will definitely visit again in the future ☺️

Bournemouth Seafront, Summer Timeshare apartment
We spent 6 days in an excellent accommodation and the facilities in the hotel were great. Our host was very helpful and supportive if we had any questions. We would definitely highly recommend this apartment.

2-BR Penthouse Apt. close to Beach with Pool*.
The place was just like in the photos, great attention to details and very clean. We felt very comfortable. There are clear instructions for self check-in and the bonus is that Matt is really involved and caring about his guests.

The Palms, Apartment 19
Clean, classy and caring.
Quick stats about vacation rentals with a pool in City of Winchester
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- New Forest national park
- Bournemouth Beach
- Kimmeridge Bay
- Paultons Park Home of Peppa Pig World
- Oxford University
- Boscombe Beach
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Southbourne Beach
- Twickenham Stadium
- Chessington World of Adventures Resort
- West Wittering Beach
- Thorpe Park Resort
- Arundel Castle
- Highclere Castle
- RHS Garden Wisley
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Marwell Zoo
- Worthing Pier
- Highcliffe Beach
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