
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.

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.

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.

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.

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

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.

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

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.

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.

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!

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.

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.

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
Family-friendly home rentals with a hot tub

San Giovanni in Poggio, Villa Meriggio 95 sqm

Agriturismo La Villa - L'Olivo, Pool & Hot Tub

Romantic Siena summer spa Francigena road

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Penthouse in Siena near Piazza del Campo and Palio

Luxury frescoed apartment in the historical center

Villa'Colombaiolo di Marciano', 28

Montalcino Townhouse with Private Garden & Spa
Family- and pet-friendly home rentals

Beautiful medieval village!!!

Archi, Rustic apartment in Tuscany

Panoramic attic in old town of Siena

Podere Piazza house with panoramic view

Stilnuovo apartment in the heart of Siena

Monteriggioni Castello, holiday house in Tuscany

Liberty Siena Flat 2

Your Tuscan oak tree house, enchanting Val d'Orcia
Family-friendly home rentals with a pool

Infinity pool in Chianti area

StageROOM03 - Idyllic Chianti cottage near Siena

Loggia 1 in farmhouse with shared pool

Esplora la natura al centro di Vigneti Chianti

Explore Chianti from a Charming Stone House

Podere Casalino – La Pergola

Siena Country Loft Hideway

Agriturismo I Gelsi
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
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!
Destinations to explore
- Flat rentals Siena
- Rentals with breakfast Siena
- Rentals with an EV charger Siena
- Villa rentals Siena
- Rentals with a patio Siena
- Cottage rentals Siena
- Pet-friendly rentals Siena
- Rentals with outdoor seating Siena
- Boutique hotels Siena
- Serviced apartment rentals Siena
- House rentals Siena
- Bed and breakfasts Siena
- Apartment rentals Siena
- Fitness-friendly rentals Siena
- Rentals with pools Siena
- Rentals with a washing machine and dryer Siena
- Rentals with a firepit Siena
- Rentals with a hot tub Siena
- Holiday home rentals Siena
- Smoking-friendly rentals Siena
- Hotel rooms Siena
- Rentals with a fireplace Siena
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Piazza della Signoria
- Mercato Centrale
- Strozzi Palace
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Eremo Di Camaldoli
- Cala Violina
- Siena Cathedral
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Pitti Palace
- Gulf of Baratti
- Things to do Siena
- Art and culture Siena
- Sightseeing Siena
- Food and drink Siena
- Nature and outdoors Siena
- Things to do Siena
- Sports activities Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Food and drink Siena
- Art and culture Siena
- Tours Siena
- Things to do Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Tours Italy
- Art and culture Italy
- Food and drink Italy
- Sports activities Italy
- Sightseeing Italy
- Wellness Italy
- Nature and outdoors Italy
- Entertainment Italy






