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Holiday rentals with a pool in Willingen (Upland)

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Willingen (Upland)

  • Total holiday rentals

    Explore 10 holiday rentals in Willingen (Upland)

  • Nightly prices starting at

    Willingen (Upland) holiday rentals start at $222 NZD per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Willingen (Upland) holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Willingen (Upland) rentals

  • 4.9 Average rating

    Willingen (Upland) stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Willingen (Upland)

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

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Top Guest favourite
A modern bungalow is set on a well-maintained property, featuring a smooth paved driveway and a well-kept lawn. The building showcases a combination of light and dark siding, with multiple windows allowing natural light to enter the interior.
Bungalow in Bromskirchen
4.97 out of 5 average rating, 91 reviews

Premium bungalow, near Winterberg, accessible

The barrier-free and wheelchair-accessible bungalow offers plenty of space with its 105 square meters. Whether on the terrace in the garden, in front of the cozy fireplace in the living area or in the extra large bathtub. On rainy days, the Curve Design TV with SKY and entertainment system invites you to relax on the genuine leather sofa. A PS4, game collections, children's books and a foosball table are available for younger guests. After an active day, use the infrared sauna with mood lighting and radio for up to 4 people.

Top Guest favourite
A scenic view of a two-part building adorned with a covered terrace featuring wooden accents. A walking path leads alongside the structure. A dog is seen in the foreground, with trees in the background contributing to the natural setting.
Home in Olsberg
4.95 out of 5 average rating, 41 reviews

Waldparadies Sauerland

Welcome to our charming, separate apartment on the first floor of a cozy single-family home where we live with our dog on the ground floor. This special accommodation is located directly on the edge of the forest on a quiet street, surrounded by beautiful nature – ideal for nature lovers and those seeking peace and quiet. Near us is probably the most beautiful part of the Ruhr Valley bike path with forest, meadows and waters. Well-marked hiking trails along the Ruhr, Olsberger Kneippweg with pedal pool.

Superhost
A spacious garden area features a covered heated pool beneath a transparent enclosure. A shaded seating area includes lounge chairs, and a wooden dining table is surrounded by greenery. The well-maintained lawn extends across the yard, providing a relaxing outdoor space.
Cottage in Waldeck
4.66 out of 5 average rating, 98 reviews

Spacious family / children's paradise on Lake Eder

Welcome to our beautiful vacation home on the Scheid peninsula, located on the beautiful Edersee. Relax and clear your head? Then this is the place for you! This is what awaits you with us, among other things: - 3.5 bedrooms - 2 modern bathrooms - terrace - cellar bar - Modern kitchen - Heated pool, sauna and gym (can be booked as a package) - covered table tennis area - Sports area with volleyball and badminton net - In addition: horizontal bar, trampoline, climbing frame, covered barbecue.

Guest favourite
A charming villa is situated amidst lush greenery, featuring a gabled roof and a welcoming front entrance. A stone pathway leads up to the door, bordered by vibrant landscaping and trees. The expansive windows offer views of the scenic countryside.
Home in Diemelsee
5 out of 5 average rating, 10 reviews

Villa Diemelsee

Herzlich willkommen in der Villa Diemelsee – Diese luxuriöse Ferienoase leigt in Alleinlage umgeben von grünen Wäldern und dem klaren Wasser des Diemelsees. Genießen Sie den eigenen Wellnessbereich der Villa mit Sauna, Pool und Whirlpool. Das Ferienhaus bietet Platz für bis zu fünf Personen. Die Räume sind liebevoll eingerichtet. Die voll ausgestattete Küche bietet alle Annehmlichkeiten. Die Lage der Villa hat direkten Zugang zu Wander- und Radwegen der Region Diemelsee und Willingen.

Guest favourite
Chalet in Winterberg
4.93 out of 5 average rating, 14 reviews

Vacation home 1000 mountains Winterberg fireplace & jacuzzi

Inmitten der Hügel und Wälder des Sauerlands erwartet dich ein besonderer Ort: unser Ferienhaus 1000 Berge – ein Platz zum Wohlfühlen, Loslassen und Kraft tanken. Ob mit Familie, Freunden oder auf vier Pfoten – hier beginnt deine Auszeit. Starte den Tag mit einer Wanderung durch die Natur, entspanne am Abend im holzbefeuerten Whirlpool unter freiem Himmel oder genieße auf der Terrasse ein kühles Sauerländer Bier. 1000 Berge ist mehr als ein Ferienhaus – es ist dein Zuhause auf Zeit.

Guest favourite
Apartment in Winterberg
5 out of 5 average rating, 5 reviews

Winterberg - Pool - Sauna - Golfplatz - Ski

Welcome to our vacation rental in Winterberg, which sleeps up to 6 people. Feel free to enjoy the large balcony with a grill, the pool, or the sauna. The Skiluft is just a few minutes’ walk away, and an 18-hole golf course is located right behind the apartment. Hiking, biking, skiing, and many other recreational activities are available year-round. Perfect for families or friends looking for a relaxing getaway in a prime location. The sauna operates on coins (2 EUR).

Superhost
A heated whirlpool is shown on a terrace, surrounded by green plants. In the background, a village with a church tower and residential buildings is visible. Comfortable seating areas are present nearby, offering a relaxed ambiance.
Apartment in Marsberg
4.91 out of 5 average rating, 227 reviews

The apartment

Our apartment has a beautiful view of the surroundings. From the panoramic window, or from one of the terraces. A terrace invites you to chill and is elevated right in front of the door. On the second terrace is the hot tub, grill, seating and fireplace. Parking is included. Wi-Fi is included. Our apartment is modernly equipped. 65-inch flat-screen TV and much more. The hot tub is heated and is there for your own use all year round. There are no other guests.

Guest favourite
The exterior of a spacious traditional half-timbered house is visible, featuring a combination of dark wood and white siding. A large balcony with red umbrellas is seen, alongside modern solar panels on the roof. Lush greenery surrounds the property, enhancing its natural setting.
Home in Medebach
4.96 out of 5 average rating, 125 reviews

House on the wild Aar 16 people

Haus am Wilde Aar can accommodate up to 16 people. This vacation home is part of a half-timbered farmhouse from 1880 that was completely renovated and modernized in 2015. The vacation home has a large garden directly on the stream and is very suitable for families and friends with children. You can enjoy the tranquility and beautiful surroundings during your stay. Thanks to the spacious layout of the house, you can enjoy plenty of privacy and relax together.

Guest favourite
The image captures two guests relaxing in a heated container pool, overlooking the surrounding landscape and charming village. Lush greenery frames the scene, while the distant hills provide a serene backdrop. The clear water reflects the sky, inviting moments of tranquility.
Home in Willingen
5 out of 5 average rating, 13 reviews

Inge in will-INGE-n, holiday home with sauna and pool

INGE is new in 2024! Inge is a modern vacation home in Sauerland in the resort of Willingen (Upland). The house is built in a special construction on steel stilts on a steep slope and offers a great view of the village and the surrounding area. As a special highlight, Inge offers its guests a heated container pool (April to mid-October). In the meantime, in addition to the fireplace, the small barrel sauna also provides cozy hours for two.

Guest favourite
An inviting seating area features a plush gray chair and a sofa with a streamlined design. A rustic wood coffee table is accompanied by a tall vase containing decorative branches. Soft lighting accentuates the wood-paneled walls, creating a cozy atmosphere.
Chalet in Meschede
4.95 out of 5 average rating, 37 reviews

Chalet in Sauerland❤ exclusive log cabin_New 2020

Own exclusive chalet hut (for 2 people) directly on the pond with unique views of the countryside. Enjoy the tranquility in this exclusively furnished house located on the edge of the forest. We have furnished our accommodation with a lot of love for detail, with high-quality natural materials. In 2015/2016, this log cabin, unique in the Sauerland, was newly renovated and we now welcome you to a relaxing holiday ❤.

Guest favourite
An inviting living area features a comfortable seating arrangement with a dark sofa and light throw blanket. A sleek coffee table is positioned in front, with decorative items displayed. Large windows allow natural light to fill the space, complemented by a modern wall art piece and stylish lighting.
Apartment in Winterberg
4.9 out of 5 average rating, 86 reviews

Cityflair 6 Pers Pool Sauna Wifi PS4 Bikepark

Welcome to Winterberg Cityflair. Our apartment is located directly "Am Waltenberg" the heart of Winterberg. From here you can reach numerous restaurants, bars and shopping within walking distance. The largest ski resort north of the Alps, the Winterberg ski lift carousel, is 150 m away. Winterberg Bike Park is 3 minutes away by bike. A place to experience adventure, breathe and relax.

Guest favourite
The historical Wassermühle is nestled in a lush green valley, surrounded by dense woods. The charming building features a distinct red roof and multiple windows. Two unique structures are visible in the foreground, enhancing the serene landscape.
Farm stay in Waldeck
4.89 out of 5 average rating, 46 reviews

Historic romantic Mill

Build in 1717 by the Prince of Waldeck, the historical monument water mill lies lonely in the midst of dreamlike nature in the natural reserve Wattertal. Affectionately restored, we offer you 6 dreamlike rooms for your holidays, seminars or events. Unfortunately, due to the sharp rise in energy prices, I have to charge an additional fee, which is noted under the "Cleaning" item.

Popular amenities for Willingen (Upland) rentals with a pool

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