
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.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
4.96 out of 5 average rating, 156 reviews
Casa al Gianni - Hut
Hello, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farmhouse 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 holiday; it’s a return to our roots. This peaceful haven will stay with you forever. We look forward to welcoming you!
4.93 out of 5 average rating, 294 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
4.92 out of 5 average rating, 627 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
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.
4.92 out of 5 average rating, 359 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
4.99 out of 5 average rating, 116 reviews
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.
4.98 out of 5 average rating, 107 reviews
Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
4.98 out of 5 average rating, 160 reviews
Casa dell'Onda 25
Welcome to our charming apartment in the historic centre of Siena, just 100 m from Piazza del Campo and 350 m from the Duomo. A haven of peace, expertly renovated to offer you maximum comfort while preserving its charming, original rustic style. It offers a bright living room, a fully equipped kitchen, an elegant bedroom and a panoramic view of the city that will make your stay unforgettable. Traditional restaurants and shops are right on the doorstep.
4.94 out of 5 average rating, 106 reviews
Luxury frescoed apartment in the historical center
The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.
4.97 out of 5 average rating, 116 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
4.89 out of 5 average rating, 311 reviews
Terrace on the walls of Siena - Casa Laura
Elegant apartment in the center of Siena with a large terrace, 600 m from the stadium and 1 km from Piazza del Campo. Located on the 4th floor (elevator up to the 3rd), it offers 2 double bedrooms, 2 bathrooms, an equipped kitchen, air conditioning in every room and a beautiful panoramic terrace above the historic walls. In the limited traffic zone. Perfect for experiencing Siena in comfort!
5.0 out of 5 average rating, 110 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
4.91 out of 5 average rating, 100 reviewsPopular amenities for Siena family-friendly rentals
Family-friendly home rentals with a hot tub

La Villa farm stay - L'Olivo, Pool & Hot Tub
4.98 out of 5 average rating, 241 reviews
"Villa Daisy" overlooking Siena
4.95 out of 5 average rating, 174 reviews
Casa Dolce Toscana | Panoramic Suite with a View
4.98 out of 5 average rating, 187 reviews
Amazing Tuscany Villa, FREE parking
4.92 out of 5 average rating, 338 reviews
La Casetta
4.93 out of 5 average rating, 197 reviews
Villa di Geggiano – Guesthouse
4.99 out of 5 average rating, 155 reviewsWp Relais Villa Vignalunga
4.93 out of 5 average rating, 117 reviews
Palazzo Monaci - Pool in the Crete Senesi
4.96 out of 5 average rating, 142 reviewsFamily- and pet-friendly home rentals

CASA WOW panoramic terrace * . *
4.98 out of 5 average rating, 107 reviews
Claudia's House in Piazza del Campo
4.93 out of 5 average rating, 111 reviews
The Door Next Door 2.0
4.97 out of 5 average rating, 229 reviews
Beautiful medieval village!!!
4.99 out of 5 average rating, 475 reviews
A BALCONY ON THE PIAZZA OF THE PALIO
4.87 out of 5 average rating, 271 reviews
•Il Chiostro• A gem in the heart of Siena
4.89 out of 5 average rating, 123 reviews
Emily's home
4.97 out of 5 average rating, 158 reviews
Manor House - IlVillinoFarmhouse
4.93 out of 5 average rating, 256 reviewsFamily-friendly home rentals with a pool

Comfort Apartment in the Chianti Vineyards
4.93 out of 5 average rating, 455 reviews
Podere La Castellina - No. 1 COTTAGE
4.97 out of 5 average rating, 162 reviews
Loggiato 2 Apartment in Tuscany with pool
4.94 out of 5 average rating, 161 reviews
Elegant farmhouse Siena
4.96 out of 5 average rating, 168 reviews
Spedaletto Castle, Val d'Orcia, Pienza
4.97 out of 5 average rating, 185 reviews
Tuscan Barn Apartment for 6 with panoramic pool
4.89 out of 5 average rating, 100 reviews
Panoramic farmhouse with pool - Big Apartment
4.98 out of 5 average rating, 101 reviews
Borgo Ripostena – No. 9 Oil Mill
4.94 out of 5 average rating, 118 reviewsDestinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
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- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
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- Things to do Italy
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