
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.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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.

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.

"Sunflower" apartment with view of Siena
Caggiolo is a completely renovated farm consisting of several apartments, each with a private entrance and exclusive use of the garden, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc). From the farm, you can hike to the Grotti Castle (6 km) or to our pond (2.5 km)

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.

Palazzo del Taja - in the center with whirlpool
Brand new apartment just renovated, located inside the historic Palazzo del Taja in the heart of Siena's historic center, a few meters from Piazza del Campo and the city's main attractions. Subjected to a renovation attentive to details, the apartment is elegant, bright, welcoming and quiet. Complete with every comfort, including a beautiful bathroom with a whirlpool tub, to offer an unforgettable stay to our customers.

Terrace with a view of Siena
A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
Popular amenities for Siena family-friendly rentals
Family-friendly home rentals with a hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Wp Relais Borgo Vignalunga

Amazing Tuscany Villa, FREE parking

Penthouse in Siena near Piazza del Campo and Palio

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villa'Colombaiolo di Marciano', 28

VILLA Amazing pool , tennis , 7km Florence,

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

Beautiful medieval village!!!

Celeste – The color of the summer sky in Tuscany

A BALCONY ON THE PIAZZA OF THE PALIO

Podere Piazza house with panoramic view

Panoramic attic in old town of Siena

Monteriggioni Castello, holiday house in Tuscany

Poggio del Fattore-Villa with pool, hilltop, Chianti

Suite in Castello di Valle
Family-friendly home rentals with a pool

Family Forest - Pool in the Crete Senesi

Stone House with Exclusive Pool Codilungo in Chianti

Podere Tignano, 4-bedroom villa in the Chianti!

Explore Chianti from a Charming Stone House

Siena Country Loft Hideway

Villa Isabella

Elegant farmhouse Siena

Very cosy cottage with beautiful views
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £95 | £84 | £107 | £118 | £120 | £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!
Destinations to explore
- Hotel rooms Siena
- House rentals Siena
- Rentals with a washing machine and dryer Siena
- Boutique hotels Siena
- Rentals with a firepit Siena
- Cottage rentals Siena
- Villa rentals Siena
- Smoking-friendly rentals Siena
- Apartment rentals Siena
- Rentals with outdoor seating Siena
- Rentals with an EV charger Siena
- Rentals with breakfast Siena
- Bed and breakfasts Siena
- Rentals with a hot tub Siena
- Serviced apartment rentals Siena
- Holiday home rentals Siena
- Pet-friendly rentals Siena
- Rentals with pools Siena
- Flat rentals Siena
- Rentals with a patio Siena
- Fitness-friendly rentals 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
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Marina di Cecina
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Strozzi Palace
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Basilica Di San Miniato A Monte
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Eremo Di Camaldoli
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- Palazzo Vecchio
- Things to do Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Sightseeing Siena
- Things to do Siena
- Sports activities Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Things to do Italy
- Sports activities Italy
- Nature and outdoors Italy
- Food and drink Italy
- Entertainment Italy
- Sightseeing Italy
- Tours Italy
- Art and culture Italy
- Wellness Italy






