Vacation 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

Top guest favorite
An open-plan kitchen and dining area is featured, with a wooden table surrounded by upholstered chairs. A well-equipped kitchen is visible, along with a cozy lounge consisting of large sofas. Natural light fills the space through large windows, offering views of the outdoor deck.
Home in Dorset
4.97 out of 5 average rating, 31 reviews

Luxury 2 bdr lodge, dog friendly,close to Mudeford

DavidRating, 5 stars3 days ago
It was a very nice lodge clean and tidy only 5 minutes ti the beach sainsbury just 2 minutes away and host good communication
Guest favorite
An outdoor swimming pool is surrounded by sun loungers and vibrant flower beds filled with red and purple blooms. Clear blue skies provide a bright backdrop to the serene scene, enhancing the sense of relaxation and leisure by the poolside.
Home in Downton
4.9 out of 5 average rating, 153 reviews

Coastal, New Forest 3 Bed Home Facilities Included

EmmaRating, 5 stars1 week ago
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! 🩷
Superhost
A scenic view is presented from the expansive decking area, featuring a rainbow arching over the tranquil Solent and Bay. The landscape includes soft, grassy fields that stretch toward the water, framed by gentle hills in the distance.
Home in Isle of Wight
5 out of 5 average rating, 5 reviews

Starfish Lodge Discounted ferry sailings available

Ms Gemma RoseRating, 5 stars3 weeks ago
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 :)
Top guest favorite
A spacious gated deck is shown, featuring a dining table surrounded by chairs. Sunlight filters through the trees, illuminating the area. The deck provides access to an entrance with glass doors leading into the holiday home.
Home in Saint Leonards
4.98 out of 5 average rating, 53 reviews

Pet friendly 2 bed holiday home

AimeeRating, 5 stars3 days ago
Just back from a lovely couple of days here. We took our 2 children (11 and 9) and also 2 dogs. The caravan is very homely and everyone settled in really well. We had a very warm weekend but the caravan stayed fairly cool and the decking gets a lot of shade so both us and the dogs stayed very cool and comfortable. The swimming pool area was great and the kids thoroughly enjoyed the outdoor area as well as the indoor slide. Very easy access to woodland for a nice long walk which we took advantage of both days. Lee and Leigh have been great hosts. Nothing seemed to be a problem to ask and were always very quick to respond to my messages. Thanks again and we will definitely be returning.
Top guest favorite
A cozy lounge area features a large TV mounted on the wall, with a beautiful image displayed. A light-colored coffee table holds a pink drink and a bowl of fruit. The room is illuminated by natural light streaming through the large windows, complemented by decorative flowers.
Home in Friars Cliff
4.97 out of 5 average rating, 33 reviews

Hoburne Holiday Park Home by the beach in Dorset

JaneRating, 5 stars3 weeks ago
My daughter and I had a fabulous stay at Crystal Moon, it was like home from home. Anita has thought of everything! All your possible needs. Beautiful caravan inside and out, a wonderful holiday park with its leisure centre and lots to do locally. We loved it and will be back! Thank you Anita
Top guest favorite
A modern caravan is set on a grassy area, featuring a spacious front deck with white railing. Two black chairs are positioned on the deck, providing an outdoor seating option. Large windows allow natural light into the interior space.
Home in Hillway
5 out of 5 average rating, 31 reviews

Rosie’s Isle of Wight Caravan - Whitecliff Bay

NARating, 5 stars5 days ago
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!
Top guest favorite
A cozy living area is showcased with a spacious sofa and an open-plan kitchen in the background. Dining table is set with decorative items, and light fixtures provide gentle illumination. Large windows offer glimpses of the outdoor surroundings, enhancing the inviting space.
Home in Saint Leonards
4.95 out of 5 average rating, 19 reviews

Sapphire @ Oakdene Forest Park

FelicityRating, 5 stars1 month ago
Fantastic stay on a lovely site. Very quiet corner location, tucked away although main parking space is under a tree so try to avoid if you don’t want lots of bird poo on your car!! Very clean caravan with lots of very thoughtful extras for every kind of guest. WiFi very reliable, access passes to site amenities sent over without needing to ask and clear instructions given for check out. Would stay here again.
Top guest favorite
Home in Hampshire
4.98 out of 5 average rating, 86 reviews

Eden Cottage, your home away

JoannaRating, 5 starstoday
My husband & I and our husky spent 3 night’s at Eden Cottage and really enjoyed our stay! Kevin & Debbie were super helpful before and during our stay, with clear info on getting there, facilities available, and local recommendations, and were really lovely people to chat with. Their 3 Labradors were adorable! The cottage was very comfortable and clean, with all we needed for a relaxing stay, a comfy bed, great shower and well equipped kitchen, with some welcome treats! It’s set in a lovely large garden, which we and our dog enjoyed spending time in. The pool was a fab bonus; clean, warm and with towels provided. Kevin’s book ‘Reckless’ is well worth a read! The cottage is a 3-min walk to the Spread Eagle pub, which does a fantastic Sunday roast, and 10 mins walk into Liss is Turtle Bean cafe, serving tasty lunches; both places are dog friendly, and there’s a lovely IPC church 5 mins walk away. All in all, a great weekend and we will definitely visit again! Thank you, Kevin & Debbie!

Condo rentals with a pool

Guest favorite
A heated communal swimming pool is framed by well-maintained hedges and lush greenery. The clear blue water reflects the sky, while poolside lounge chairs provide space for relaxation. The distant view of the coastline adds a scenic backdrop to the peaceful setting.
Condo in Isle of Wight
4.97 out of 5 average rating, 39 reviews

Beautiful 3-bed flat by the sea with use of pool

VictoriaRating, 5 stars2 months ago
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.
An indoor pool area features a crystal-clear water surface under a spacious glass ceiling. A sliding board is positioned on one side, while lounge chairs are arranged nearby. Potted plants add greenery, and large windows provide views of the landscaped gardens outside.
Condo in Dorset

Holiday apartment own heated indoor pool & sauna

GrahamRating, 5 stars34 months ago
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 ;-)
Top guest favorite
An open-plan living area features a plush sectional sofa facing a large television. A wooden bar counter with three high chairs enhances the space, while artwork adorns the wall. Natural light is diffused through large windows, contributing to a bright atmosphere.
Condo in Isle of Wight
4.91 out of 5 average rating, 22 reviews

Luxury Penthouse: Spacious & Stylish

HannahRating, 5 stars3 weeks ago
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.
A serene view of a marina is framed by two large trees, with numerous boats docked in the water. Lush greenery is visible in the foreground, leading to the expansive waterfront. The sky features soft hues as the day transitions.
Condo in Hampshire

Luxury 2 Bedroom Apartment - New Forest

ChloeRating, 5 stars11 months ago
Wonderful, well appointed apartment over 2 floors. Large balcony with a lovely view. We shall definitely return if we can
Superhost
An indoor pool area is highlighted, featuring a curved shape surrounded by light tiles and equipped with multiple white lounge chairs positioned at the edge. Natural light is captured from above, creating a bright and inviting environment for relaxation and leisure.
Condo in Sandown
4.94 out of 5 average rating, 16 reviews

Balcony On The Bay - FREE Car Ferry 3+ nights

EleanorRating, 5 stars2 months ago
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 ☺️
An indoor pool area is enclosed by large glass windows, allowing natural light to illuminate the clear water. Lush green plants are positioned around the pool, enhancing the calming atmosphere. A glimpse of the outdoor pool and landscaped gardens can be seen through the windows.
Condo in Central
5 out of 5 average rating, 3 reviews

Bournemouth Seafront, Summer Timeshare apartment

SvetlanaRating, 5 stars22 months ago
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.
Guest favorite
An aerial view of the apartment building is shown, with the sea visible in the distance. Surrounding residential buildings and roads are clearly depicted. A green area with trees is present in front of the building, along with parked cars lining the street.
Condo in East Southbourne
4.83 out of 5 average rating, 41 reviews

2-BR Penthouse Apt. close to Beach with Pool*.

ClaudiaRating, 5 stars2 days ago
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.
Superhost
The exterior of a modern three-story apartment building is captured, featuring a blend of white and stone facades. Large windows and a peaked roof characterise the architectural style. A sign identifying the property is prominently displayed at the entrance, surrounded by neatly landscaped greenery.
Condo in Westbourne
4.75 out of 5 average rating, 4 reviews

The Palms, Apartment 19

EmilyRating, 5 stars35 months ago
Clean, classy and caring.

Quick stats about vacation rentals with a pool in City of Winchester

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$6,276 GYD 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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