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

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!

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.

Florentine Hills “Le Scalette”
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.

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.

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!

"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.

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.

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.

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.

Countryside Dream farm in Tuscany
Great place 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.
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

Torretta Apartment

Beautiful renovated barn in Tuscany

Tuscan cottage, sea view and private olive garden

Villa di Geggiano – Guesthouse

House for 2/3 people in Fonteregia farmhouse

Green Dome @ The Land Before Time Retreats

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

Florence Country Side: Giogoli a place to be!

Love in Chianti

Belforti Tower

Casa Al Poggio & Chianti view

Three-room apartment SUP Mandarino - Fattoria di Colleoli

Borgo Ripostena – No. 8 Casa Vecchia

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Inserted Hunting Lifestyle Building in Tuscany
Family-friendly home rentals with a pool

Villa Due Pini Marti with private pool

GIRASOLE (sleeps 4) Farmhouse "SERACINO"

Rosa: Tuscan Views & Pool, Walk to Town

Tuscan Luxury Villa • Natural Pool & Privacy

Castel San Giorgio

Rural Loft with magical Tuscan Views

BorgoMetato - Magione

"Le Querce" Glamping Tent with Jacuzzi
Destinations to explore
- House rentals Santa Maria a Monte
- Flat rentals Santa Maria a Monte
- Rentals with outdoor seating Santa Maria a Monte
- Rentals with a fireplace Santa Maria a Monte
- Rentals with a patio Santa Maria a Monte
- Rentals with pools Santa Maria a Monte
- Rentals with a washing machine and dryer Santa Maria a Monte
- Pet-friendly rentals 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
- Fortezza da Basso
- Piazza della Repubblica
- Uffizi Gallery
- Mugello Circuit
- Del Chianti
- Gorgona
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Parco delle Cascine
- Gulf of Baratti
- Basilica of Santa Croce
- Medici Chapel





