Family-friendly holiday rentals in Poppi

Holiday home in loc. Simignano

A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.

Casa al Gianni - Oak

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

FamilyKitchenParking

4.93 out of 5 average rating, 244 reviews

5.0 out of 5 average rating, 218 reviews

An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.

Condo in Noce

Historic 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills, and vineyards with breathtaking sunsets.

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 192 reviews

The rustic farmhouse is set against a clear blue sky, featuring a textured stone façade with wooden window shutters. A gravel courtyard is visible, adorned with potted plants and outdoor seating, offering a welcoming entrance to the tranquil countryside surroundings.

Farm stay in Reggello

Stone farmhouse, exclusive private pool

Podere Montebono is located in the hills of Reggello, just 30 kilometers from Florence. Ideal for reaching art cities and natural sites. The farmhouse is isolated on a hill, immersed in nature, surrounded by olive trees, a garden, and woods. The guest house is an independent wing of the large farmhouse on two floors: 3 bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.

KitchenFamilyWalkability

5.0 out of 5 average rating, 27 reviews

A dining area features a round wooden table surrounded by modern chairs. Two large woven pendant lights hang above, illuminating the space. Sunlight filters through a window adorned with wooden shutters, creating a bright and airy atmosphere. A doorway leads to another room.

Apartment in Poppi

Historic Apartment in Poppi in Casentino

In the medieval village of Poppi, in a historic building, Casa Fresia was born: a refuge in the heart of the Casentino for those who love Tuscany and want to spend a vacation between history and nature. A short walk from Casa Fresia, you can visit the Castle of Conti Guidi dating back to 1191 and still perfectly preserved. From Poppi you can set off on cultural itineraries, visiting castles, parish churches and sanctuaries, or on nature itineraries, discovering the Casentino Forests.

KitchenIndoor spacesCheckout

4.99 out of 5 average rating, 226 reviews

The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.

Castle in Ferrano

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Indoor spacesFamilyWalkability

Villa in Barberino Tavarnelle

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

KitchenFamilyHospitality

4.98 out of 5 average rating, 105 reviews

Farm stay in Greve in Chianti

A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Indoor spacesFamilyLaundry

4.99 out of 5 average rating, 431 reviews

5.0 out of 5 average rating, 66 reviews

An aerial view of a rustic villa is framed by lush greenery, showcasing a stone exterior and terracotta roof tiles. A salt-water pool is situated nearby, surrounded by outdoor seating. The tranquil landscape of hills is visible in the background under warm evening light.

Home in Poppi

Villa Podere Cerretino

Podere Cerretino is the perfect place to find and discover your own tranquility and relaxation. A corner of paradise surrounded by the picturesque hills of Tuscany in an enchanting landscape, located in a central and strategic position to visit the most interesting places in Tuscany, such as Florence, Siena, Arezzo. The Villa consists of 4 completely independent apartments and an elegant panoramic veranda where you can gather and enjoy a unique vacation.

FamilyIndoor spacesCheck-in

4.96 out of 5 average rating, 138 reviews

The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.

Castle in Bagno A Ripoli

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Indoor spacesFamilyCleanliness

Holiday home in Chiusi della Verna

An ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.

Experience rustic off-grid life in the wilderness

This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

FamilyKitchenAmenities

4.97 out of 5 average rating, 157 reviews

4.97 out of 5 average rating, 32 reviews

A historic tower is visible amidst lush greenery in the garden area. Surrounding plants, including trees and shrubs, create a serene atmosphere. A stone seating area is positioned at the center, providing an inviting spot for relaxation in this tranquil outdoor space.

Apartment in Poppi

Country chill in the heart of a medieval village

Historic structure from the 1600s, located in the center of the medieval village of Poppi, with a large garden available. The apartment offers three double bedrooms, a living room, a kitchen, and a bathroom. We can add one small single bed in one of the bedrooms if necessary. The apartment is part of a larger property that extends in the heart of the town's historic center, yet it is completely surrounded by greenery.

KitchenFamilyBreakfast

4.95 out of 5 average rating, 124 reviews

A charming rural building is set against a backdrop of lush greenery at dusk. Soft lighting highlights the stone exterior and terracotta roof, while the surrounding trees and landscaped grounds enhance the tranquil environment.

Farm stay in Anghiari

Mafuccio Farmhouse - "Casa di Rigo"

Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

KitchenFamilyLaundry

Popular amenities for Poppi family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 122 reviews

A private outdoor space features a Jacuzzi surrounded by stone paving, with the house visible in the background. The two-story structure has wooden windows and doors, creating a welcoming setting. Nearby shrubbery and a tree provide additional greenery and shade.

Home in Stia

Country house with view (NO Jacuzzi)

Indoor spacesKitchenLong stay

Home in Terranuova Bracciolini

Villa Lolù with private heated swimming-pool

FamilyIndoor spacesQuiet

4.97 out of 5 average rating, 159 reviews

Farm stay in Monte San Savino

A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

FamilyKitchenBarbecue

4.99 out of 5 average rating, 113 reviews

Villa in Castiglion Fiorentino

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Tuscan charm of villa - countryside - Villa Senaia

FamilyKitchenCheck-in

4.9 out of 5 average rating, 240 reviews

Home in Figline e Incisa Valdarno

Well-maintained gardens feature a lush lawn surrounded by mature trees, providing shade. An old stone building is visible in the background, characterized by arched windows and a terracotta roof. A shaded outdoor seating area, under a rustic wooden eave, adds to the inviting exterior.

Torretta Apartment

KitchenFamilyLaundry

4.97 out of 5 average rating, 128 reviews

Home in Rignano sull'Arno

A rustic two-story structure is framed by lush greenery, showcasing stone and brick elements. Windows are adorned with decorative iron bars and window boxes, adding character. The inviting exterior is complemented by a blue sky and gentle hillside, creating a serene countryside setting.

LA CASA DELL' AMBRA-ANCIENT BARN RENOVATED-

KitchenIndoor spacesSleep quality

4.92 out of 5 average rating, 157 reviews

Farm stay in Gaiole in Chianti

A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.

La Pieve - the house next to the church

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 115 reviews

4.88 out of 5 average rating, 221 reviews

Holiday home in Reggello

Barrel Suite Tuscany • Hot Tub • Vineyard View

Indoor spacesFamilyHospitality

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 278 reviews

An inviting living area features a stone fireplace framed by a wooden mantel. A circular dining table is set with colorful tableware, surrounded by wooden chairs. Woven armchairs add comfort, and natural light enters through a wooden door next to an intricately framed wall hanging.

Apartment in Stia

House by the river, view of the castle

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 150 reviews

The image depicts a medieval village set against a backdrop of rolling hills, with a prominent stone castle tower. Traditional stone buildings with terracotta roofs line the foreground, creating a charming landscape. The setting conveys a sense of history and natural beauty.

Apartment in Porciano

La Casina Porciano

FamilyKitchenCleanliness

4.88 out of 5 average rating, 338 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

KitchenFamilyAccuracy

Apartment in Pratovecchio Stia

A rustic stone house is situated among lush greenery, framed by old trees displaying autumn foliage. The building features multiple windows and a welcoming presence, surrounded by a mostly open landscape with gentle slopes and natural stone elements.

Podere La Quercia

KitchenIndoor spacesCondition

4.99 out of 5 average rating, 118 reviews

4.98 out of 5 average rating, 54 reviews

A private terrace is seen, featuring a large umbrella shading a small table and two chairs. Stone steps lead to the entrance of the apartment, surrounded by plants and stone walls characteristic of the historic architecture.

Home in Poppi

historical townhome in Poppi

KitchenFamilyWi-Fi

5.0 out of 5 average rating, 5 reviews

Villa in Poppi

Poggelleri the postcard on Poppi and Tuscan hills

Indoor spacesAmenitiesHospitality

Villa in Castel San Niccolò

The historic villa features a charming stone exterior, accented by lush greenery and flower boxes. Large arched windows provide views of the surrounding parkland, while a covered terrace extends along the front, offering additional outdoor space for relaxation.

Villa Mondello inTuscany great view

FamilyIndoor spacesBathroom

4.94 out of 5 average rating, 48 reviews

4.95 out of 5 average rating, 19 reviews

A serene outdoor area features two wooden lounge chairs positioned beside a modern infinity pool. The pool reflects the landscape of rolling hills and distant historic structures, with lush greenery surrounding the space, creating a tranquil setting for relaxation.

Home in Poppi

Casentino Villa Antonella

FamilyIndoor spacesBathroom

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 113 reviews

Home in Greve in Chianti

Relaxation and charm in the Chianti hills

FamilyKitchenLong stay

4.96 out of 5 average rating, 169 reviews

A serene outdoor pool is surrounded by well-maintained greenery and blooming lavender. Comfortable lounge chairs are placed under shaded umbrellas, offering a peaceful spot to relax while enjoying views of the expansive Tuscan landscape and distant hills.

Farm stay in Pian di Scò

Agriturismo I Gelsi

Indoor spacesFamilyLocation

Farm stay in Loro Ciuffenna

The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.

Il Roseto: your Villa in Tuscan Countryside

Indoor spacesFamilyDecor

4.99 out of 5 average rating, 123 reviews

4.99 out of 5 average rating, 100 reviews

The outdoor pool features clear turquoise water, surrounded by a stone patio. Lush green hills and tall cypress trees create a scenic backdrop, while a few lounge chairs are positioned nearby for relaxation.

Home in Subbiano

Romantic cosy flat - Toscana Italy

FamilyIndoor spacesLocation

5.0 out of 5 average rating, 12 reviews

A well-maintained garden surrounds a private swimming pool, measuring 9 by 4 meters. Several sun loungers are positioned around the pool, offering relaxation space. The backdrop features tall cypress trees and views of nearby greenery, along with a distant glimpse of a historic castle.

Villa in Poppi

Cipressino Villa, pool near the historic centre

Indoor spacesKitchenWalkability

5.0 out of 5 average rating, 48 reviews

A serene outdoor swimming pool reflects the surrounding greenery, flanked by lounge chairs and shaded areas. The historic building in the background is surrounded by tall cypress trees, overlooking the gently rolling hills of Tuscany.

Home in Farneta

Podere Bocci residence in Casentino - Entire Villa

FamilyKitchenLocation

4.86 out of 5 average rating, 7 reviews

A tranquil swimming pool is surrounded by sun loungers and flowering plants. Two large umbrellas provide shade, while scenic views of the green hills and blue sky create a serene backdrop. The pool area is well-maintained and invites relaxation or leisure activities.

Villa in Poppi

Villa for 22 people w/private pool

FamilyIndoor spacesCondition