
Family-friendly holiday rentals in Santa Maria a Monte
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Top-rated family-friendly rentals in Santa Maria a Monte
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Love in Chianti
Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

The MOONLIT & SUNNY COTTAGE near Florence
IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

San Miniato - Panoramic terrace in the historic center
Brand new apartment in the historic center of San Miniato. Recently renovated, it is ideal for those seeking tranquility in the heart of the city, with a beautiful view of the Tuscan countryside thanks to the panoramic terrace perfect for a breakfast in the sun or a special aperitif. Immersed in the historic part of the city, typical restaurants, shops and all the beauties of San Miniato can be easily reached on foot. Thanks to its central location, it is ideal for visiting all of Tuscany.

Tuscan cottages in an ancient villa with a garden
The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

House at Gianni - Olmo
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!

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Countryside Dream farm in Tuscany
Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

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.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Lovely countryhouse on Chiant hills
Lovely view on the valley, sweet relax in the smelling garden under a very old tree tasting a good wine and then to visit Firenze, Pisa, Siena only 30 km far from here and medieval castles,little churchs ,winery,across the beautiful Chianti road.....

Cottage near Pisa Lucca Florence #1
Cottage surrounded by greenery, woods and olive trees and a wonderful panoramic view. A short walk from the town center and close to the cities of Lucca, Pisa S.Gimignano, and Florence. A very large and bright bedroom and a fully equipped kitchen.
Popular amenities for Santa Maria a Monte family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

La Bruna

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Tuscan cottage: sea view and private olive garden

Il Fienile di Tigliano (former barn in Vinci-Florence)

"Gigi's House" (GG House)

House for 2/3 people in Fonteregia farmhouse

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

Open Space Piscina e Giardino

Belforti Tower

Charming apartment "Orangerie", Borgo ai Lecci

Trosce Lost-in-nature villa with breathtaking view

Secret Garden Siena

Suite in Castello di Valle

[Toscana] Between Pisa, Lucca and Florence!

Private Villa with semi-Olympic pool and Tennis
Family-friendly home rentals with a pool

GIRASOLE (sleeps 4) Farmhouse "SERACINO"

Amazing view, pool and relax, 5 adults

Tuscan Luxury Villa • Natural Pool & Privacy

Castel San Giorgio

Rural Loft with magical Tuscan Views

Villa sii felice

Le Querce, ap. "Rosmarino", relax in Tuscany!

Original Tuscan Experience in the Heart of Chianti
Quick stats about holiday rentals that are family-friendly in Santa Maria a Monte

Total holiday rentals
Explore 30 holiday rentals in Santa Maria a Monte

Nightly prices starting at
Santa Maria a Monte holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 700 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

Wifi availability
30 of Santa Maria a Monte holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Santa Maria a Monte rentals

4.8 Average rating
Santa Maria a Monte stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Flat rentals Santa Maria a Monte
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- Rentals with a washing machine and dryer Santa Maria a Monte
- House rentals Santa Maria a Monte
- Rentals with a fireplace Santa Maria a Monte
- Rentals with a patio Santa Maria a Monte
- Rentals with outdoor seating Santa Maria a Monte
- Rentals with pools Santa Maria a Monte
- Family-friendly rentals Pisa
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Fortezza da Basso
- Mugello Circuit
- Gorgona
- Piazzale Michelangelo
- Spiagge Bianche
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Parco delle Cascine
- Gulf of Baratti
- Medici Chapel
- Basilica of Santa Croce
- San Terenzo Beach





