
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.

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

Tuscan Villa for Family & Friends in Montepulciano
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

[Luxury Apartment]WiFi-Private Garden-Free Parking
Splendida casa, situata a soli 5 minuti in auto dal centro storico di Siena, dagli spazi ampi e lussuosi. Finemente ristrutturata con utilizzo di materiali pregiati, in questo lussuoso immobile potranno soggiornare fino a 6 ospiti. La sua centralissima posizione, ad appena 5 minuti in auto dal centro storico di Siena, i tantissimi servizi che si trovano intorno alla casa e la zona tranquilla che la circonda, ne fanno la location ideale per un piacevole soggiorno a Siena.

Casa al Gianni - Fig
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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.

The Door Next Door 2.0
Charming apartment in rustic style. It is located in the historic center of Siena in a perfect location for visiting all the historical sites, attractions and shopping area of Siena on foot. In five minutes, you can reach Piazza del Duomo with its museum and the "Santa Maria Assunta" Cathedral. 600 meters away you can reach the enchanting Piazza del Campo where the "Palio", the traditional horse race, takes place on July 2 and August 16.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Balconies
This small apartment is located on the second floor (by the lift) of an historical Palazzo (Palazzo Saracini) over the Piazza del Campo. The uniqueness of the apartment is the presence of two balconies that allow direct view of the Piazza del Campo. CIN (national identification code) IT052032C25H6ZF3G5
Popular amenities for Siena family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

Beautiful renovated barn in Tuscany

Charming estate with views. A/C in the bedrooms

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Penthouse in Siena near Piazza del Campo and Palio

Villa'Colombaiolo di Marciano', 28

Tuscany View - Villa Arianna
Family- and pet-friendly home rentals

Casa Borgianni in Villa Caprera

Beautiful medieval village!!!

A BALCONY ON THE PIAZZA OF THE PALIO

Elegant fine home 400 m away from Piazza del Campo

Panoramic attic in old town of Siena

Your Tuscan oak tree house, enchanting Val d'Orcia

At Paola's in Chianti

La Dimora del Luca
Family-friendly home rentals with a pool

Cozy country house Podere Scorno with pool

Infinity pool in Chianti area

Podere La Castellina - No. 3 JUNIPER

Stone House with Exclusive Pool Codilungo in Chianti

Charming home Crete Senesi

Explore Chianti from a Charming Stone House

Siena Country Loft Hideway

Antico Borgo Ripostena – n. 8 Old House
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £95 | £84 | £107 | £118 | £121 | £132 | £127 | £128 | £128 | £124 | £107 | £118 |
| 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 560 holiday rentals in Siena

Nightly prices starting at
Siena holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 29,110 verified reviews to help you choose

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wifi availability
540 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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