Family-friendly vacation rentals in Siena

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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 favorite

Villa in Monteriggioni (SI)

4.97 out of 5 average rating, 149 reviews

FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) Siena is the closest town (12 min by car) and Florence is 45 min away

Guest favorite

Rental unit in Centro Storico

4.97 out of 5 average rating, 106 reviews

CaseMaggi Florence Historic City Center Apartment

Welcome to CaseMaggi Holiday Homes. This historic apartment is in the heart of Florence near Piazza Sant'Ambrogio, the Synagogue, a 10 min walk to the Duomo, Santa Croce and museums but in a classic quiet neighborhood filled with restaurants and a famous open market. The apartment has been remodeled protecting its 15th century stone wall, cotto floors and frescoed master bedroom ceiling with full modern kitchen. Antique art and furniture adorn it. We also have apartments in Portovenere.

Guest favorite

Rental unit in Centro Storico

4.97 out of 5 average rating, 119 reviews

Complimentary wine w/ infra-red Sauna

Welcome to our luxury home, a contemporary-styled, sophisticated 4 bed flat in a Renaissance-era setting that offers guests the perfect blend of old and new. There is taste and elegance in every detail that combines contemporary design and style, alongside the structure's original Renaissance features. Nestled in the heart of Florence’s Oltrarno quarter it is located just a stone’s throw from the Ponte Vecchio and lively streets dotted with shops, bars, restaurants, and artisan workshops.

Guest favorite

Rental unit in Centro Storico

4.91 out of 5 average rating, 143 reviews

NEW: Romantic Apartment in Oltrarno, San Frediano

Bright and airy, fully air con, newly renovated to high spec 2 bed /1 bath apartment on the top floor of a 2 unit building dating back to the 1400's in the charming historical San Frediano district, an easy few minutes walk to all the main sights. According to Lonely Planet, San Frediano is the 1st world’s coolest neighbourhoods to visit. There is no lift, there are 28 steps, not many but quite challenging. Regional identification code CIR 048017LTN8197

Guest favorite

Home in Certaldo (Fi)

4.87 out of 5 average rating, 60 reviews

Paluffo Torre House

This is the antic tower of the villa and it is built on three levels and features a private garden and a marvellous view of the Chianti hills and San Gimignano. • Ground-floor: living room with a fireplace, bathroom and dining room with kitchen. • First floor: double bedroom with private bathroom and studio with sofa bed. • Second floor: 2 double bedrooms with bathroom.

Guest favorite

Villa in Orentano

4.96 out of 5 average rating, 100 reviews

Charming Villa in Stone in Tuscany, Borgo ai Lecci

The location, easily accessible, is perfect for visiting the main attractions in Tuscany: the cities of art, the old villages, beautiful landscapes and many other points of interest in this amazing region. Or relax and feel like you are at home. This charming well-maintained Villa in Stone is part of a complex of three buildings used for higher-level holiday homes.

Superhost

Rental unit in Chianni

4.77 out of 5 average rating, 210 reviews

Piccola Corte

Romantic typical Tuscan accommodation with outdoor space for soft dinners. Available for couples and small families. Central to the medieval Etruscan village village. All shops and main amenities nearby (bank, mail, gas station) . Typical products: Quality wine and oil. Close to the theater of silence of Bocelli ,Volterra 30 km, Pisa 45 km ,sea at 35 km.

Guest favorite

Rental unit in Centro Storico

4.87 out of 5 average rating, 227 reviews

Total Florence 100%

Beautiful bright and quiet apartment in the heart of residential Florence, just a few steps from the best restaurants in Florence and a 10-minute walk from the David Academy, San Lorenzo and the Central Market. Perfect for large families or large groups of friends, it offers a spacious living area to stay together and large private bedrooms.

Guest favorite

Villa in Bagno a Ripoli

4.97 out of 5 average rating, 119 reviews

Quite old farmhouse on the hills of Florence

Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 25 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more!