Vacation rentals with a pool in Winchester

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

An indoor swimming pool is set within a spacious enclosure, featuring a clear roof that allows natural light to filter through. The water is calm and inviting, surrounded by tiled flooring. Lush greenery is visible through the transparent walls, adding a natural element to the setting.

Vacation home in Hawkley

4.99 out of 5 average rating, 139 reviews

Daily Red Kite Feeding/Pool - Countryside Lodge

JUNIPER HOUSE AIRBNB - Peaceful, getaway lodge in the heart of Hampshire’s beautiful Hangars. We offer: - Daily Red Kite & Badger feeding, viewed from inside comfortable conservatory, with tea, coffee and refreshments! 30-90 Red Kites during each feeding/up to 10+ badgers! - Milk, bread, spread, tea: Provided upon arrival. - Indoor swimming pool, with full access; no permission required, 24/7. - Thirty acres of private garden/woodland to explore! - Free, on-site parking; multiple spaces.

Top guest favorite

A private swimming pool is set within a stone patio, surrounded by lush greenery. The water exhibits a bright blue hue, and steps lead gracefully into the pool. Nearby seating areas and the exterior of the barn can be glimpsed in the background.

Barn in Wroxall

4.99 out of 5 average rating, 120 reviews

Idyllic, private & unique countryside holiday

Our Granary is a stylish, sustainable barn conversion set in idyllic countryside at the end of a quiet country lane, surrounded by a horseshoe of downs and near wonderful beaches. It truly is a picturesque spot, and all just 3 hours from London. The Granary has just been renovated from two agricultural buildings. With two comfy bedrooms, a large kitchen diner to inspire a great meal, a lounge with a wood burner and a huge window seat in which to gaze out at the garden, courtyard and the pool.

Top guest favorite

A clear view of the spacious backyard features a heated swimming pool in the foreground, surrounded by a wooden deck. A grassy area extends toward the house, which is designed with large windows and a patio with outdoor seating, providing a serene outdoor environment.

Home in West Sussex

4.98 out of 5 average rating, 103 reviews

Spacious house and garden in Itchenor

Located in Shipton Green, Itchenor, The Willows is surrounded by large gardens with tennis court and heated swimming pool. Close to W. Wittering Beach and Itchenor Harbour, and with easy access to local walks, bike rides and waterside pubs. Near Chichester and Goodwood. 'WOW. The house is absolutely fantastic, we couldn't have asked for a better setting to celebrate Christmas. If you are looking for a spacious, beautiful property then this is a must book house. We will 100% be back'. Dec 2021

Guest favorite

The exterior of a luxury period property is showcased, featuring a large garden area with lush green grass. The house displays a blend of brick and greenery, including a charming conservatory with numerous windows. Trees frame the property, enhancing the serene outdoor setting.

Home in Hampshire

4.9 out of 5 average rating, 167 reviews

Arnewood Rise, a holiday home in New Forest & pool

Arnewood Rise is a luxury period property located in the heart of the New Forest. It is the perfect holiday home for big groups of all ages and fully equipped for fun times indoors and out. The grounds span 5.5 acres, including 1.5 acres of landscaped gardens with a heated outdoor swimming pool, a tennis court and 4 acres of fields complete with two ponies. It is ideally located within walking distance of the open national park and a short drive from the coastline and the many pretty villages.

Top guest favorite

An indoor heated swimming pool is showcased, surrounded by large glass windows that provide views of the surrounding woodland. Comfortable seating is arranged nearby, and wooden beams create a warm ambiance throughout the space.

Tiny home in Isle of Wight

4.93 out of 5 average rating, 193 reviews

Delightful Chalet Bungalow with a Spa

This beautifully presented chalet is within an old vineyard in a woodland area on the outskirts of Ryde ,with stunning views around the property. Although secluded, it is just a short distance to Ryde town centre & beaches . The property boasts a living/dining room with a smart tv and dining table and chairs , one being a double sofa bed.. Walk in shower in bathroom.. The kitchen has everything you need including dishwasher… The bedroom can be made up as 2 singles or kingsize upon request.

Guest favorite

A tranquil outdoor space features a heated swimming pool surrounded by a stone patio. Lush greenery and colorful flower beds enhance the setting, with an inviting barn structure visible in the background under a clear blue sky.

Barn in West Sussex

4.95 out of 5 average rating, 124 reviews

Delightful one bedroom barn with beautiful views

Our beautiful rustic one bedroom barn is attached to the end of our family home. Situated in the popular Surrey Hills an area of outstanding beauty surrounded by many local award winning pubs and immediate access to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making Autumn and winter particularly lovely with board games available. Guests are also welcome to use the house facilities which include a heated swimming pool and tennis court.

Guest favorite

A patio dining set features a dark woven table surrounded by four comfortable chairs with soft cushions. A vase of sunflowers sits at the center of the table, complemented by blue plates and glasses. The expansive lawn offers uninterrupted views of the Solent.

Bungalow in Warsash

4.92 out of 5 average rating, 171 reviews

Panoramic Sea Views, quiet, relaxed, Cozy, Beach

A beautifully presented Chalet Bungalow based on the edge of Solent Breezes Holiday park. Full Sea views over the Solent from the comfort of the open plan kitchen diner and lounge. Light airy building ideal for relaxing either on the large leather sofa or on the rattan furniture in the garden. In all weathers there is always something to see out of the large patio doors. Stony beach and slipway for boats only metres from the property. Ideal for long walks watching the sunset and relaxing

Guest favorite

Bungalow in Bosham

4.9 out of 5 average rating, 143 reviews

Chic Bungalow Retreat - Serene Garden, Pool & Spa

A Luxurious Retreat in the Heart of Nature Nestled within the scenic South Downs, a short stroll from Bosham Harbour, Cedar Lodge is a new development offering luxury & tranquility. Less than 6 miles from Goodwood & 9 miles from West Wittering Beach, this retreat is close to the historic city of Chichester, contained within a vast 3.5-acre garden amid peaceful fields & woodlands. Key Highlights: ✔ VAT Friendly ✔ Newly Developed Location ✔ Ultimate Privacy & Security ✔ Spectacular Grounds

Top guest favorite

An outdoor pool area is visible through large sliding doors. The pool is covered and surrounded by a spacious patio made of light-colored tiles. Lush greenery and garden furniture, including a seating area and patio umbrella, can be seen in the background, enhancing the inviting outdoor atmosphere.

Place to stay in Hill Brow

4.99 out of 5 average rating, 100 reviews

The Pool House (for 2 Adults & 2 Children)

This unique, Architect designed self contained building, has a style all of its own. With an open plan kitchenette and island unit, including an oven, microwave, hob and fridge freezer, you can dine in or go out to the Market Town of Petersfield. The lounge area has a 72" TV with a full sky package and spare HDMI leads. There is a walk in shower wet room and a separate cloakroom. The bedroom is cosy, with a king size bed. There is a separate area with bunkbeds, for smaller children.

Top guest favorite

The outdoor area features a rectangular pool covered with a blue tarp, bordered by a stone deck. Decorative planters are positioned along the edge, and lush greenery surrounds the space, with tall trees visible in the background.

Shepherd’s hut in Winchester

4.96 out of 5 average rating, 395 reviews

Shepherd's Hut with Hot Tub near Winchester

Traditional shepherd's hut with a contemporary interior and private hot tub 3 miles from Winchester. En-suite shower, kitchenette, deck with table and chairs, bbq and brazier. The hut has a private location in the grounds of a country house. Guests can use the owner’s tennis court and heated outdoor pool (open May to end of September). Explore Winchester, Portsmouth, the New Forest and Hampshire’s beaches. This year-round retreat has a heated towel rail, electric radiator and WiFi.

Guest favorite

The cottage is surrounded by lush greenery and a well-maintained garden. A gravel path leads to the entrance, framed by neatly trimmed hedges. Large windows reflect natural light, while bicycles are casually positioned nearby, suggesting an inviting outdoor environment.

Cottage in Hampshire

4.94 out of 5 average rating, 200 reviews

Beautiful S.Downs Cottage, pool and tennis

A private gate takes you directly onto the South Downs with some lovely foot and cycle paths on your doorstep. Close to the beach and city, Chichester, Portsmouth, Southhampton, Winchester, Goodwood and Witterings beaches are in easy reach while Liphook station takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. The pool and tennis court are available from May to end Sept/early Oct, Mon- Sat 9am - 1 pm.

Top guest favorite

The Pool House is set against a twilight backdrop, featuring warm lights that highlight its modern design. The spacious patio area is adorned with seating and a large pool, surrounded by greenery, offering an inviting outdoor space for relaxation.

Place to stay in Stroud

4.97 out of 5 average rating, 182 reviews

The Pool House: Contemporary country escape

Enjoy a relaxing time in the heart of the South Downs. Have a dip in the pool to cool off or warm up in the hot tub. Consisting of 2 king size beds, double sofa bed, open plan kitchen, dining room and living space. Open up the bi fold doors onto a large patio area with bbq, pizza oven and eating area. Situated 1 mile from the market town of Petersfield. Country walks on the doorstep and 500m from the local pub. Only 20 mins drive to the beach its a great spot for a break.