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Family-friendly holiday rentals in Siena

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Siena

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

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5 out of 5 average rating, 303 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 114 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 311 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Top guest favourite
A bright living area features comfortable seating arranged around a glass coffee table. Light wood flooring complements the soft neutral tones of the furniture. Decorative shelves display various items, and artwork adorns the walls, enhancing the welcoming ambiance.
Flat in Siena
4.95 out of 5 average rating, 272 reviews

SAN DOMENICO LUXURY APARTMENT

Un appartamento luminoso ed accogliente nel cuore di Siena al primo piano di un palazzo storico e curato nei minimi dettagli. Dotato di una cucina, di due camere da letto e di 2 bagni. E' ideale per 4 persone. La zona è ricca di locali, ristoranti e negozi. La casa è vicina al parcheggio dello stadio ed alle stazioni degli autobus di piazza Gramsci e dei taxi di piazza Matteotti Costo per neonati a notte 20€ Check in 15-20 Check-out entro le 10.00 Codice CIN IT052032C2DTDZF9NA

Top guest favourite
A doorway opens to a warm, inviting space featuring a cozy bedroom with a spacious bed dressed in light linens. The room includes wooden ceiling beams and a small table with chairs in the background, complemented by natural light filtering through the window.
Flat in Siena
4.94 out of 5 average rating, 200 reviews

Casa Fusari - Apartment next to the Duomo

! Please check the house rules before booking ! Completely renovated apartment with fine finishes located in a building of 1746, one minute walk from Piazza del Duomo and two minutes from Piazza del Campo. Strategic position in the heart of the historic center, very convenient raised ground floor from which you can see part of the Duomo, next to the apartment you will find two great restaurants. A few steps away you will also find the escalator to the parking lot Santa Caterina.

Top guest favourite
The open-plan living area is illuminated by natural light from the large windows, featuring a dining table surrounded by four chairs. Elegant wooden beams adorn the ceiling. A modern kitchen with sleek cabinetry and a comfortable seating area is presented, creating a functional and inviting space.
Apartment in Siena
4.94 out of 5 average rating, 175 reviews

Charming apartment in the heart of Siena

The apartment is located in historic centre of Siena, in one of the fascinating streets which leads directly to the main square Piazza del Campo. Strategic location of the apartment makes it an ideal starting point for exploring Siena and it's surroundings, perfect as for single travellers and couples, as for families with kids. In the day of Palio from the windows of the apartment you can enjoy watching historical parade when passing by before entering in Piazza del Campo

Guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Flat in Castelnuovo Berardenga
4.93 out of 5 average rating, 168 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 241 reviews

Casa al Gianni - Hut

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favourite
A well-furnished terrace is shown, featuring a table with chairs and a comfortable seating area. An umbrella provides shade while potted plants add greenery. Scenic views of the countryside and historic surroundings are visible in the background, contributing to a serene outdoor atmosphere.
Flat in Siena
4.91 out of 5 average rating, 224 reviews

Zona Il Campo e Duomo casa con terrazzo panoramico

Entire bright and cozy accommodation just 200 meters from Piazza del Campo, 400 meters from the Duomo, with convenient car parking just 150 meters away. The beauty and tranquility of the countryside in the historic center, which can be enjoyed from the terrace. All services are within walking distance. Only 5 steps to the entrance.

Guest favourite
A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.
Farm stay in Gaiole in Chianti
4.94 out of 5 average rating, 250 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Top guest favourite
A balcony provides a scenic view of Piazza del Campo, showcasing the surrounding historic buildings. A small table and chair invite relaxation, while the colorful sunset casts a warm glow over the area, highlighting the lively atmosphere with people enjoying the space below.
Flat in Siena
4.86 out of 5 average rating, 258 reviews

A BALCONY ON THE PIAZZA OF THE PALIO

Three windows with balcony overlooking Piazza del Campo that allows access to an exclusive terrace with breathtaking views of the Piazza del Palio and the Palazzo Pubblico. One bedroom, large super-equipped kitchen. Sofa bed available to comfortably accommodate up to 4 people

Popular amenities for Siena family-friendly rentals

When is the best time to visit Siena?

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Avg. price$164 SGD$145 SGD$184 SGD$202 SGD$207 SGD$226 SGD$218 SGD$220 SGD$220 SGD$213 SGD$184 SGD$202 SGD
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Quick stats about holiday rentals that are family-friendly in Siena

  • Total holiday rentals

    Explore 550 holiday rentals in Siena

  • Nightly prices starting at

    Siena holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 28,980 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 210 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    520 of Siena holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Siena rentals

  • 4.8 Average rating

    Siena stays are highly rated by guests – averaging 4.8 out of 5!

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