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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 560 holiday rentals in Siena

  • Nightly prices starting at

    Siena holiday rentals start at $26 SGD 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!

Top-rated family-friendly rentals in Siena

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 337 reviews

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.

Guest favourite
The living space features high ceilings with decorative beams and elegant pendant lighting. A modern kitchen is visible, complemented by a dining table and white chairs. Two plush white sofas are arranged for comfort, with a decorative plant adding a touch of greenery.
Flat in Siena
4.91 out of 5 average rating, 258 reviews

Appartamento Palazzo Casini Piccolomini

Appartamento nuovo appena ristrutturato, situato al piano 2 dello storico Palazzo Casini Piccolomini, nel cuore del centro di Siena, a 30 metri dalla celebre Piazza del Campo, dotato di ogni confort per offrire ai nostri ospiti un soggiorno indimenticabile. Renewed apartment, located on the 2nd floor in the historic Casini Piccolomini building, in the heart of Siena downtown, at 30 metres from the famous Piazza Del Campo, fully equipped for offering to our guests a great staying in our city .

Top guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 159 reviews

Casa Dolce Toscana | Panoramic Suite & View

CASA DOLCE TOSCANA 🖼️ Ciao! Sono Jolanta 😊 Benvenuti nel nostro amato alloggio toscano ,con vista panoramica,immerso nelle colline della Toscana.Un’oasi di pace perfetta per chi desidera rilassarsi e vivere un’esperienza autentica. Situato a pochi chilometri da Siena e Firenze,il nostro alloggio combina il fascino rustico con tutti i comfort moderni. si trova nel cuore del centro storico del famoso borgo di Cetona,sottostante al castello ,con vista sulla valle e il profumo della Toscana.

Top guest favourite
A bright living area features comfortable seating arranged around a glass coffee table. Light wood flooring complements the soft neutral tones of the furniture. Decorative shelves display various items, and artwork adorns the walls, enhancing the welcoming ambiance.
Flat in Siena
4.95 out of 5 average rating, 287 reviews

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

Guest favourite
A well-lit bedroom features two spacious beds arranged together, providing flexibility for different sleeping arrangements. A desk and modern chair are positioned near the window, with decorative shelves and framed art on the walls. Soft curtains gently diffuse natural light, enhancing the inviting ambiance.
Flat in Siena
4.88 out of 5 average rating, 217 reviews

Affitti Brevi Siena - [DUOMO] Nel centro di Siena

Confortevole ed elegante appartamento arredato appositamente per viaggiatori da tutto il mondo. Situato in una posizione super centrale a 500 metri a piedi dal Duomo e da Piazza del Campo, avrete a circa 3 minuti di camminata un parcheggio coperto e molteplici fermate degli autobus nell’immediate vicinanze della casa. Sono inoltre presenti svariate strutture come, negozi, ristoranti, luoghi storici, e bar. Una posizione strategica sia che siate a Siena per lavoro o per puro svago!

Superhost
Flat in Siena
4.92 out of 5 average rating, 126 reviews

[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.

Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in Simignano
4.92 out of 5 average rating, 227 reviews

Casa al Gianni - Quercia

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!

Top guest favourite
A view captures a historic building in Siena, displaying its rustic architecture and multiple arched windows. In the foreground, trees bloom with pink flowers, while green vegetation adds a touch of nature. The iconic tower of Siena is visible in the background under a clear blue sky.
Apartment in Siena
4.97 out of 5 average rating, 217 reviews

La porta Accanto 2.0

Grazioso appartamento in stile rustico. Si trova nel centro storico di Siena in una posizione perfetta per visitare a piedi tutti i siti storici, le attrazioni e la zona dello shopping di Siena. In cinque minuti è possibile raggiungere la Piazza del Duomo con il suo museo e la Cattedrale "Santa Maria Assunta". A 600 meti é possibile raggiungere l'incantevole Piazza del Campo dove il 2 luglio e il 16 agosto si svolge il "Palio", la tradizionale corsa di cavalli.

Top guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Flat in Castelnuovo Berardenga
4.94 out of 5 average rating, 177 reviews

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.

Top guest favourite
An open living area is shown with a dining table surrounded by black and white chairs. The ceiling displays decorative beams, and light enters through a window, illuminating the space. A fireplace is positioned against one wall, with artwork adorning the surrounding walls.
Flat in Siena
4.96 out of 5 average rating, 312 reviews

Renovated flat 50 meters from Piazza del Campo

Apartment in the historic center of Siena, just 50 meters from Piazza del Campo. The accommodation was completely renovated in 2019. The restoration was carried out trying to keep its main features intact, but adding all the necessary equipment to today's way of life. The apartment is an ideal place for those who want to visit and experience the city; In fact, all the monuments and attractions of the historic center can be reached on foot in a few minutes.

Top guest favourite
Villa in Monteroni d'Arbia
4.94 out of 5 average rating, 162 reviews

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 211 reviews

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.

Popular amenities for Siena family-friendly rentals

When is the best time to visit Siena?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$193 SGD$167 SGD$203 SGD$204 SGD$209 SGD$229 SGD$221 SGD$222 SGD$222 SGD$216 SGD$186 SGD$204 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Destinations to explore

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