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

Guest favorite
An indoor swimming pool is showcased, featuring a vibrant waterslide shaped like a frog. The pool area is bright and spacious, with white walls and a high ceiling. Steps lead into the water, and seating areas are visible along one side.
Home in Isle of Wight
4.95 out of 5 average rating, 22 reviews

Discounted Ferries with Medina Rise Lodge

KerryRating, 5 stars2 months ago
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
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, 30 reviews

Luxury 2 bdr lodge, dog friendly,close to Mudeford

VictoriaRating, 5 stars3 weeks ago
Fabulous place to stay, had all we needed. Beautiful area of the country.
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, 4 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 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 stars4 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!
Superhost
Home in Bracklesham Bay
4.84 out of 5 average rating, 213 reviews

Luxury Seafront Family Home - Indoor Pool

JemmaRating, 5 stars2 weeks ago
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
Top guest favorite
Home in Hampshire
4.98 out of 5 average rating, 85 reviews

Eden Cottage, your home away

BeccaRating, 5 stars3 weeks ago
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
Guest favorite
A spacious outdoor area is seen featuring a heated private pool, surrounded by modern landscaping. A large umbrella provides shade over comfortable seating, while lush greenery and a distant sea view enhance the tranquil atmosphere.
Home in Westbourne
4.97 out of 5 average rating, 76 reviews

Incredible sea views and heated outdoor pool

IanRating, 5 stars6 days ago
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

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 stars2 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 stars1 day 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

    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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