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

Total holiday rentals
Explore 20 holiday rentals in Montespertoli

Nightly prices starting at
Montespertoli holiday rentals start at $153 NZD per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Montespertoli holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Montespertoli rentals

4.8 Average rating
Montespertoli stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Montespertoli
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Vacation immersed in the Tuscan countryside 'Canaiolo'
"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped swimming pool 🌞💐The scents of nature, breathtaking landscapes and the swimming pool will be the setting for the relaxation you seek. 🚴🏻♂️🏃♀️Then if you feel the need to move, you can swim, walk, or run along the paths around your country home. 🏛The apartment's strategic location allows you to make excursions to Florence, Siena, and Pisa. ✨The apartments have been recently renovated in Tuscan style."

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Villa i Lecci 1
At Villa i Lecci you will have an accommodation for exclusive use, surrounded by the beautiful Chianti landscape, just 1.8 km from the town center. The two double bedrooms, cozy and spacious, are connected by a corridor to the living room with fireplace and to the dining room with kitchen. Perfect for a relaxing pool vacation or a tour of Chianti and the main Tuscan cities, Florence, Siena, Pisa, San Gimignano and Volterra. Suitable for couples, families, and groups of friends.

Sunny Beauty
Tranquility - Beauty - Relaxation. We are in Chianti, San Gimignano, Florence, Siena, Volterra and Pisa are not far away. Beauty and extraordinary things surround us, as well as good genuine food, especially great wine and great oil. Fully renovated home. Note: You can find us on Google Maps. Shops close at 8:00 p.m. I am a local tour guide, I studied art and singing. I wish you a pleasant stay in my home, furnished with love and with the aim of making you feel good.

La Chicchera, ground floor apt with panoramic view
La Chicchera is a recently renovated apartment with attention to detail in a very quiet street in the centre of Montespertoli, a village in the heart of Chianti and a short distance from Florence and all the other cities of art in Tuscany. Mini-markets, bars, pharmacies, restaurants, shops, banks are within easy walking distance; bus stops are also within walking distance. We look forward to welcoming you and being part of your stay in Tuscany with tips and tricks!

I Limoni Apartment in Tuscany
In the Chianti hills between Florence Siena rich in history and evocative natural sceneries, the cradle of civilizations that have left an artistic and cultural heritage of unparalleled value, surrounded by unspoiled nature luxuriant vineyards cultivated as gardens, centuries-old olive groves, imposing cypresses, is the "VillaBassa" farm is located. easily accessible Florence 30 min Pisa 50 min Siena 50 min S.Gimignano 30 min Monteriggioni 45 min

The little house in the garden
It is a little house with two rooms: a living room with the kitchen and a double bed sleeping couch and a double bedroom; there is the bathroom with the shower and a bidet. The kitchen has a gas stove, an oven, the dishwasher, fridge and freezer. We have a TV with satellite reception, a wi- fi, heating and air-conditioning; the huge garden surrounds the house, one can use the beach loungers and the barbeque. There is a private parking space.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Chianti Panorama | House with 3 En-Suite Bathrooms
Immerse yourself in the authentic magic of Chianti 🍷 in our exclusive country home 🏡, boasting panoramic views over Montespertoli and its rolling hills . Strategically located just 1 km from the town center and main amenities 🛍️ like cafes ☕, restaurants 🍽️, and supermarkets 🛒, it is within easy reach of Florence , San Gimignano , Volterra and Siena . All the wonders of Tuscany will be just a charming day trip away!

Costalmandorlo, a rustic home in the heart of Tuscany
Costalmandorlo is your peaceful corner in the center of Tuscany. A charming country cottage restored and furnished with care and with a style that combines ancient and modern. Here you can slow down and relax surrounded by the sounds of nature, admiring beautiful sunsets and having long breakfasts in the garden. A short distance between Florence, Siena and Pisa, it is an excellent base for touring Tuscany.

A paradise terrace in Chianti between Florence and Siena
Wake up to a view of the Chianti hills, have breakfast on the terrace, and reach Florence, San Gimignano, and Siena in less than an hour. Finally, enjoy a sunset aperitif. A quiet house designed for families and friends who want to experience authentic Tuscany and enjoy the tranquility of the countryside without being isolated.
Popular amenities for Montespertoli family-friendly rentals
Family-friendly home rentals with a hot tub

Casa al Gianni - The Simignano Barn

Nada Home

Farmhouse in Chianti with Swimming Pool

Il Vichiaccio: Florence Villa with Jacuzzi

A Big Dream in a Little Tower.

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Il Fienile, Cottage in the country with Jacuzzi

Farmhouse , pool, 13 px. Lucca 10km
Family- and pet-friendly home rentals

Casa del Sole in Chianti

Lucciano "Cipresso" Farmhouse

Countryhouse 9 kms to Florence-3+2,free park, wine

Apartment in Tuscan farm house.

Luxury Villa in the very heart of Chianti

Tuscan relax appartment with private pool

Country house with shared pool in the Chianti area

Belforti Tower
Family-friendly home rentals with a pool

Relaxation and charm in the Chianti hills

Cercis - La Palmierina

Farmhouse in Tuscany hills

Stone House with Exclusive Pool Codilungo in Chianti

FIENILE VILLACOLLE Tuscan hillside

Flat for 4 with garden & pool in agriturismo

Villa Isabella

The Castle of Ferrano - Castle in Tuscany
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Val di Luce
- Porta Elisa





