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

Total vacation rentals
Explore 20 vacation rentals in Montespertoli

Nightly prices starting at
Montespertoli vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Montespertoli vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults, with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards, with incomparable sunsets.
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Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
KitchenFamilyBackyard

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."
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“Le Scalette,” Florentine Hills
The property is a portion of a 16th Century Casa Colonica (a typical Tuscan farmhouse) situated atop a hill surrounded by vineyards, olive groves and sprawling views of the surrounding hills. The village of San Vincenzo a Torri and of Ginestra Fiorentina are respectively 2km away grocery and bakery stores, pharmacy, bank, restaurant, news stands, and petrol stations are within minutes from the house. Only 16km (10miles) to Florence the toll free highway is 3km from the house. Car is a must.
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La Chicchera, ground floor apt with panoramic view
La Chicchera è un appartamento recentemente rinnovato e curato nei minimi dettagli in una via molto tranquilla del centro di Montespertoli, un paesino nel cuore del Chianti e a breve distanza da Firenze e da tutte le altre città d'arte della Toscana. Facilmente raggiungibili a piedi minimarket, bar, farmacie, ristoranti, negozi, banche; a pochi passi anche le fermate dell’autobus. Saremo felici di accogliervi e poter far parte del vostro soggiorno in Toscana con consigli e suggerimenti!
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Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.
FamilyIndoor spacesWifi

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.
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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
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Tower Penthouse in small castle near Florence
900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.
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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).
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Lucciano "Cipresso" Farmhouse
Mon logement se trouve à proximité de la magnifique vue panoramique. Situé dans la région viticole du Chianti, l’Agriturismo Lucciano est une entreprise qui produit du vin qui dispose d’un jardin, une maison avec vue sur les collines et une connexion Wi-Fi. Mon logement est adapté pour les aventuriers solitaires, les voyageurs d’affaires, familles (avec enfants), grands groupes, couples et amis à fourrure (animaux domestiques).
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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.
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Popular amenities for Montespertoli family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi
Indoor spacesKitchenGrill

Torretta Apartment
Indoor spacesFamilyGrill

SuiteLouise.pool, Hot Tub,homeGym & private Garden
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Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
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Le Rondini - where it all began
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Villa di Geggiano – Guesthouse
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Nada Home
Indoor spacesFamilyHeating

Green Dome @ The Land Before Time Retreats
Indoor spacesFamilyDecor
Family- and pet-friendly home rentals

Florence Sunset Hills • Giogoli
FamilyKitchenLocation

Beautiful medieval village!!!
Indoor spacesKitchenAir conditioning

Luxury Villa in the very heart of Chianti
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Celeste – The color of the summer sky in Tuscany
FamilyIndoor spacesCleanliness

Private villa/swimming pool in Tuscany
Indoor spacesFamilyAccess

Tuscany .Countryhouse on the Florence's hills
Indoor spacesFamilyAccess

Secret Garden Siena
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Wonderful house with garden
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Family-friendly home rentals with a pool

App.with pool and beautiful view, 5 adults
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Farmhouse in Tuscany hills
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Tenuta Chiudendone in Tuscany
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Private Chianti Cottage, Garden & Vineyard Views
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Cercis - La Palmierina
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Belforti Tower
FamilyKitchenCheck-in

Tuscan Farmhouse – Private Pool & Chianti Views
FamilyKitchenAccess

Stone House with Exclusive Pool Codilungo in Chianti
Indoor spacesKitchenComfort
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)
- Mugello Circuit
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Spiagge Bianche
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Basilica of Santa Croce
- Medici Chapel





