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Family-friendly holiday rentals in Santa Maria a Monte

Find and book unique family-friendly homes on Airbnb

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 $65 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!

Top-rated family-friendly rentals in Santa Maria a Monte

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

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Top guest favourite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay in Simignano
4.91 out of 5 average rating, 270 reviews

Casa al Gianni - Fig

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Top guest favourite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5 out of 5 average rating, 269 reviews

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.

Top guest favourite
A terrace showcases a small table set with glasses and a bottle, complemented by two chairs. A scenic view of the Tuscan countryside can be seen in the background, revealing rolling hills and traditional rooftops under a bright sky.
Flat in San Miniato
4.99 out of 5 average rating, 166 reviews

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.

Top guest favourite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home in Vaiano
4.99 out of 5 average rating, 275 reviews

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.

Top guest favourite
An inviting kitchen space is highlighted by an arched brick entry. A large wooden dining table is set in the foreground, adorned with a decorative centerpiece. The kitchen features modern appliances, including a silver refrigerator, and warm lighting enhances the rustic ambiance.
Villa in Canneto, San Miniato
4.94 out of 5 average rating, 127 reviews

Tuscany Country House Villa Claudia

Vivi l’incanto della nostra Country House: un antico casale toscano di pregio, finemente restaurato, con vista mozzafiato sul borgo di Canneto (785 d.C.). Immersa nel verde di San Miniato e dotata di ogni lusso moderno, la villa è un rifugio esclusivo per rigenerarsi. Scegli tra il relax totale nella Jacuzzi in giardino, tour enogastronomici d'eccellenza o visite alle vicine città d’arte toscane. Un’esperienza sensoriale indimenticabile tra storia e natura. Prenota il tuo sogno in Toscana!

Superhost
The exterior of the farmhouse showcases a three-story stone structure with a rustic charm. Surrounded by a grassy area, the building features a variety of windows and a distinct roofline, with a tree providing shade nearby.
Farm stay in Capannori
4.94 out of 5 average rating, 139 reviews

"Gigi's House" (GG House)

Welcome to "La Casa di Gigi" — a charming, historic farmhouse nestled in the heart of Tuscany. Located just 9 km from the enchanting city of Lucca, 30 km from Pisa and the coast, and about 50 km from Florence, it’s the perfect base to explore the best of the region. Lovingly named after our beloved Uncle Gigi (Zio Gigi) — the last family member to call this house home full-time — "La Casa di Gigi" holds the warmth of family memories and the timeless character of rural Tuscany.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 141 reviews

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.

Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.96 out of 5 average rating, 135 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favourite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay in Palaia
4.98 out of 5 average rating, 191 reviews

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.

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.

Top guest favourite
Farm stay in Pisa
4.99 out of 5 average rating, 328 reviews

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.

Top guest favourite
A warm dining area is illuminated by natural light streaming through large windows. A wooden table, adorned with a bowl of oranges, sits at the center, while nearby upholstered chairs offer a cozy seating option. Exposed wooden beams add character to the room.
Cottage in Montespertoli
4.93 out of 5 average rating, 276 reviews

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.....

Popular amenities for Santa Maria a Monte family-friendly rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Santa Maria a Monte
  6. Family-friendly rentals