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Holiday houses in San Francesco

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Top-rated holiday rentals in San Francesco

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Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 180 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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 seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Top Guest favourite
Home in Pontassieve
5 out of 5 average rating, 61 reviews

La Quercia House in the countryside

In a panoramic position 15 km from Florence, it is the only apartment in an ancient restored barn. Suitable for those who want to enjoy the peace of the countryside but also comfortably visit places of art. 3 km away are the towns of Pontassieve and Sieci with all services including railway stations from which, in 20 minutes, you can reach the center of Florence. The wonderful countryside and the proximity to the historic buildings including the church of San Martino make the place enchanting.

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Guest favourite
A salt-water swimming pool is set within a stone patio, featuring gentle steps leading into the water. Surrounded by greenery, the area offers views of a rustic house and landscaped gardens, contributing to a serene atmosphere.
Farm stay in Rignano sull'Arno
4.95 out of 5 average rating, 63 reviews

Agriturismo in Chianti Hills, 12 km from Florence

230+ EXCELLENT REVIEWS on TRIPADVISOR. 29 YEARS in BUSINESS. YOU CAN TRUST US!!!! HOUSE "CASA GIOTTO" in VILLA CAFAGGIOLO is an Authentic Tuscan Agiturismo located in the CHIANTI HILLS. Swimming pool with SALT WATER. 7 hectares of land (Vineyards, Olive Trees...) 2 Elegant GAZEBOS surrounded by OLIVE GROVE. We produce 5 EXCELLENT WINES and a BIOLOGIC EXTRA VIRGIN OLIVE OIL Lots of Activities and Services for you. COOKING CLASSES, PRIVATE DINNER with PRIVATE CHEF, OLIVE OIL TASTING...

Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 222 reviews

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.

Guest favourite
A serene bedroom is illuminated by two pendant lights, creating a soft ambiance. A spacious bed is dressed in neutral linens, accompanied by a blanket draped over the side. Large windows with light, flowing curtains offer a view of the lush green surroundings.
Apartment in Pelago
4.91 out of 5 average rating, 35 reviews

Elegant riverside retreat near Florence

Welcome to our elegant suite on the banks of the River Sieve, just 20 km from Florence – perfect for guests traveling by car. Enjoy peaceful river views, lush green surroundings, and a newly renovated interior with a cozy living room and spacious terrace. We’re 2 km from Pontassieve (about a 20-minute walk), where frequent trains reach Florence in just 20 minutes. “The Mall” luxury outlet is only a 15-minute drive, making this the ideal base for a relaxing Tuscan getaway.

Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 222 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 427 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Top Guest favourite
A wooden cabin is surrounded by lush greenery, featuring a covered patio with lounge chairs. An outdoor wooden tub is situated nearby, with landscaped gravel and stones creating a natural setting. Large windows offer views of the tranquil forest, enhancing the serene atmosphere.
Cabin in Leccio
5 out of 5 average rating, 45 reviews

Cabin in the woods in Tuscany with exclusive bathtub

You'll stay in a fantastic and exclusive wooden cabin nestled in a forest in a fabulous natural park in the Florentine hills. Twenty minutes from Florence and at the gates of Chianti, you can fully connect with nature while enjoying every comfort: the cabin is equipped with a large exclusive outdoor tub (unheated), air conditioning, kitchen, bathroom with hydromassage shower, large covered outdoor patio to dine or enjoy an aperitif from our farm.

Top Guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 134 reviews

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.

Top Guest favourite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home in Fiesole
4.99 out of 5 average rating, 310 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

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, 214 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.

Popular amenities for San Francesco holiday rentals

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