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Family-friendly vacation rentals in Willingen (Upland)

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Willingen (Upland)

  • Total vacation rentals

    Explore 260 vacation rentals in Willingen (Upland)

  • Nightly prices starting at

    Willingen (Upland) vacation rentals start at G$12,558 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,750 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Willingen (Upland) vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    Willingen (Upland) stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Willingen (Upland)

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
The modern structure displays a clean, white facade accented by dark trim. A balcony extends above the entrance, featuring an umbrella for shade. A wooden bench is positioned outside, providing a serene spot to enjoy natural surroundings.
Home in Diemelsee
4.95 out of 5 average rating, 113 reviews

SAUERLAND vacation home on Lake Diemelsee (Heringhausen)

Enjoy your vacation in the Sauerland in our lovingly furnished vacation home overlooking Lake Diemelsee, which is only 150 meters away!! The 109 sqm of living space are distributed over two bedrooms, a separate TV room, the spacious living-dining room with fully equipped kitchen, hallway, bathroom on the first floor with large sauna and the second bathroom on the upper floor. Two storage rooms offer enough space for bicycles, skis and everything that is bulky. One of the highlights: The large roof terrace with lake view!

Guest favorite
A bright living area features a large, light-colored sectional sofa adorned with an accent pillow. A round wooden coffee table rests on a circular area rug, and a decorative plant adds greenery. Large glass doors lead to a balcony, framed by sheer drapes.
Apartment in Winterberg
4.92 out of 5 average rating, 116 reviews

Apartment Tokio + Sauna, 100 m to Ski and Bikepark

Diese moderne 70 m² Ferienwohnung inkl. privater Sauna liegt direkt an der Skipiste und dem Bikepark – ideal für einen Aktivurlaub mit Entspannung. Zwei Schlafzimmer mit Boxspringbetten und eine Schlafcouch bieten Platz für bis zu 6 Personen. Die voll ausgestattete Küche, ein stilvolles Bad mit Dusche und zwei Balkone schaffen eine gemütliche Atmosphäre. WLAN, Netflix und Waipu-TV sind inklusive. Ein Tiefgaragenstellplatz steht dir ebenfalls zur Verfügung – für einen rundum sorglosen Aufenthalt.

Guest favorite
Apartment in Willingen
5 out of 5 average rating, 16 reviews

*| Chalet-Suite |* by Meis I Willingen (Upland)

Welcome to the chalet suite in the heart of Willingen – pure relaxation awaits! This stylishly furnished suite combines the charm of the region with modern comforts and offers everything you need for a relaxing stay: → King-size bed for a restful sleep → Smart TV + comfortable seating areas → Free Wi-Fi → Parking included + private bicycle storage → Fully equipped kitchen with automatic coffee machine + dishwasher → Bathroom with modern shower → Washing machine + large balcony for relaxation

Guest favorite
A small balcony is furnished with two striped chairs and a round table. Two glasses filled with a reddish beverage are placed on the table. The view includes lush greenery and distant hills under a partly cloudy sky.
Apartment in Willingen
4.85 out of 5 average rating, 127 reviews

Best location with ✰mountain views✰, parking and Netflix

Lovingly furnished in the most modern style. The location of our apartment is the absolute highlight, to the center of Willingen you need only 2 minutes walk, then you will find the most popular places such as Brauhaus, Dorf Alm etc.. Despite the central location, you have a sensational view of nature and the mountains of Willingen on the balcony. There are enough free parking spaces that belong to the apartment building. In our apartment you can enjoy your vacation directly after entering.

Superhost
A dining area features a wooden table surrounded by six chairs, with warm yellow walls adding a cheerful touch. Soft lighting hangs above the table, and large windows allow natural light to enter, overlooking a garden. A cozy seating area is positioned in the corner.
Vacation home in Willingen
4.83 out of 5 average rating, 101 reviews

Cozy accommodation with its own sauna

This beautiful accommodation with space for 5-6 people offers space for relaxation and fun with friends and family. The beautiful, quiet location is perfect for a trip to Sauerland. Restaurants, shopping and leisure activities are within walking distance. The small balcony is perfect for breakfast or to drink a glass of wine together in the evening. For even more relaxation, you can use the private sauna, for example in the evening. Looking forward to seeing you soon!

Top guest favorite
The exterior of a black vacation home features a prominent chimney and large windows that allow natural light inside. Surrounding greenery includes a lush bush and a well-maintained garden, providing a serene outdoor ambiance.
Cottage in Willingen
4.95 out of 5 average rating, 370 reviews

The little black dress

The little black one! A charming cottage on the Musenberg. A beautiful colorful cottage garden welcomes guests. The covered terrace invites you to enjoy the outdoors. For grilling and cooking, use the outdoor oven. (Spring to fall) The bright house, which is converted into the roof, is decorated with a lot of love. Experience relaxing days surrounded by nature! Hiking and cross-country skiing right outside the door. Pets are welcome upon request. Maximum 1 dog.

Guest favorite
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
4.95 out of 5 average rating, 127 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 favorite
A scenic view is captured from the balcony, showcasing rolling green hills and distant mountains. The landscape includes a mix of trees and residential buildings, while fluffy clouds drift across a clear blue sky.
Apartment in Willingen
4.9 out of 5 average rating, 100 reviews

Harmony in Willingen - Schwalefeld

Ruhig und doch nicht ab vom Schuss - in ca. 4 Autominuten seid ihr in Willingen und könnt das volle Programm genießen... Der Preis beinhaltet die Kurtaxe von 2€/Person/Nacht. Bettwäsche und Handtücher sind ebenfalls im Preis inbegriffen. Hinweis: Es handelt sich hierbei um eine AirBnB-Wohnung und nicht um eine gewerbliche Ferienwohnung oder ein Hotel. Bestimmte Services, wie z.B. kurzfristiges Wechseln der Handtücher o.Ä., sind deswegen nicht möglich.

Superhost
A wooden cabin is nestled among lush greenery, accented by blooming flowers in vibrant colors. The sloped roof and large windows hint at a welcoming interior. The surrounding trees provide a natural backdrop, enhancing the serene atmosphere of the location.
Cabin in Willingen
4.9 out of 5 average rating, 401 reviews

Woody Willingen - The wooden hut in beautiful nature

This cozily furnished Scandinavian wooden cabin in Willingen-Bömighausen will delight you. Surrounded by forest, meadows and pastures, this charming cabin is not only suitable for recreation and relaxation. In addition to its ideal starting point for hiking (directly on the Uplandsteig), cycling and excursions to the beautiful region, it is only a few kilometers away from the Willingen ski area. Dogs are welcome! (€30 fee per stay)

Guest favorite
A dining table is set with green plates and wine glasses, with a bouquet of yellow flowers as the centerpiece. The view beyond features rolling hills under a partly cloudy sky, allowing natural light to illuminate the inviting dining space.
Apartment in Winterberg
4.96 out of 5 average rating, 147 reviews

Sun Panorama - Adventurers and Explorers

Welcome to Sonnen Panorama in Grönebach near Winterberg! Enjoy the magnificent view over the Sauerland, the quiet location and the comfort of our modern ground-floor apartment. With a balcony, fireplace, private garage, dog-friendly and child-friendly amenities, and a perfect location for hikers, cyclists, families, and winter sports enthusiasts, it is the ideal base for your getaway in nature.

Guest favorite
An open living area is presented with a dark floor and slanted ceiling. A glass dining table with chairs sits in the foreground. A cozy seating arrangement with black sofas is located nearby, complemented by a light from a floor lamp and a wall-mounted television.
Apartment in Willingen
4.9 out of 5 average rating, 135 reviews

Wohlfühlen Willingen - Apartment Bernhard

Bernhard vacation apartment Attic apartment for max. 6 people (adults) Features: 3 bedrooms including a crib 1 bathroom with shower/bathtub and toilet Fully equipped kitchen High chair TV with radio reception in the living room Outdoor patio, lawn and children's swing A linen package (on loan) consisting of bed linens and 2 towels per person is also included in the price.

Superhost
A traditional two-story house with a timber-framed facade is presented. The exterior features white walls accented by dark beams, complemented by multiple square windows that allow natural light. A single door is centered at the front, framed by steps leading to the entrance.
Cottage in Olsberg
4.9 out of 5 average rating, 217 reviews

Charming house "Alte Försterei" in Sauerland

This historic 19th century house with modern interior (6-10 Guests) is part of the Bruchhausen Castle Estate with a view on the Castle and the park. The house is very bright, has a private garden and terrasse as well as outside parkingspace for two cars. From the house you can see on top of the mountaine the 4 massiv rocks "Bruchhauser Steine".

Popular amenities for Willingen (Upland) family-friendly rentals