
Family-friendly holiday rentals in Siena
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Siena

Total holiday rentals
Explore 570 holiday rentals in Siena

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

Verified guest reviews
Over 29,640 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
300 properties have a dedicated workspace

Wifi availability
550 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!
Top-rated family-friendly rentals in Siena
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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.

Casa al Gianni - Il Fienile di Simignano
Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

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.

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.

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.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Terrazza sulle mura di Siena- Casa Laura
Elegante appartamento in centro a Siena con terrazza abitabile, a 600 m dallo stadio e 1 km da Piazza del Campo. Situato al 4° piano (ascensore fino al 3°), offre 2 camere matrimoniali, 2 bagni, cucina attrezzata, aria condizionata in ogni stanza e una splendida terrazza panoramica sopra le mura storiche. In ZTL. Perfetto per vivere Siena in pieno comfort!

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?

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.
Popular amenities for Siena family-friendly rentals
Family-friendly home rentals with a hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Amazing Tuscany Villa, FREE parking

White lily con vista su Siena

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

La Casa di Nada Home

Villa’Colombaiolo di Marciano',28

Domus Nannini - Loggia Salimbeni SPA

Palazzo del Taja-in pieno centro con idromassaggio
Family- and pet-friendly home rentals

Tuscan cottage with an heavenly view

La porta Accanto 2.0

Vintage apartment 400m PalioPiazza del Campo Siena

Podere Piazza casa con vista panoramica

•Il Chiostro• Una chicca nel cuore di Siena

Monteriggioni Castello, holiday house in Tuscany

Agriturismo Poggio Bicchieri ap. Memoria

Villa Bonelli - La Magnolia Apartment
Family-friendly home rentals with a pool

Farmhouse apartment with pool

Infinity pool in Chianti 1

Siena - appartamento in campagna vicino Siena

Podere La Castellina - N°3 GINEPRO

Stone House with Exclusive Pool Codilungo in Chianti

Explore Chianti from a Charming Stone House

Relax e charme tra le colline del chianti

House Rigomagno Siena
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £111 | £96 | £117 | £122 | £131 | £132 | £128 | £128 | £128 | £125 | £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 |
Destinations to explore
- Cottage rentals Siena
- Rentals with breakfast Siena
- Boutique hotels Siena
- Holiday home rentals Siena
- Serviced apartment rentals Siena
- Pet-friendly rentals Siena
- Rentals with pools Siena
- Bed and breakfasts Siena
- House rentals Siena
- Villa rentals Siena
- Apartment rentals Siena
- Flat rentals Siena
- Hotel rooms Siena
- Rentals with a hot tub Siena
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Stazione Santa Maria Novella
- Mugello Circuit
- Uffizi Gallery
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
- Boboli's Garden
- Mount Amiata
- Things to do Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Sightseeing Siena
- Food and drink Siena
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Food and drink Siena
- Tours Siena
- Sports activities Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy







