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Holiday rentals in San Gemignano

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Top-rated holiday rentals in San Gemignano

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Townhouse
4.88 out of 5 average rating, 336 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Guest favourite
The exterior of the house features a two-story structure with large windows and a covered terrace, surrounded by lush greenery and colorful flowers. An infinity pool stretches out in front, reflecting the mountains in the background, creating a serene outdoor space.
Home
4.95 out of 5 average rating, 63 reviews

Infinity pool Pisa-Lucca-Florence View all around

Beautiful house with spectacular views and infinity pool. Very private, no other guests or sharing anything. This is something else. Villa Vetteglia is built on a hilltop, the views are 360 degrees. 3 bed (with AC) and 3 bath (beds 7/8 are a comfortable pull out bed in the living room) The location is private and remote yet close to Lucca, Pisa, Florence. Bagni di Lucca (for shopping) is 7km. About the location, it is on a asphalted mountain road, but see the pics before you make a booking :)

Top guest favourite
A traditional stone house is set against a backdrop of gently sloping greenery. The structure features terracotta tiles and several windows that reflect the surrounding landscape, while well-maintained shrubs and trees flank the property, offering a sense of tranquility.
Bungalow
4.94 out of 5 average rating, 36 reviews

The Vineyard

'Il Vigneto' is a traditional stone house with terracotta tiles and exposed beams. A magnificent swimming pool over seven meters in length benefits from having full sun throughout the day. Adjacent to the pool is an extensive outdoor eating area along with a built-in BBQ. and Pizza oven. Inside, the house is spacious and immaculate with a modern, fully equipped kitchen/dining room, that also contains a sofa bed. There are two double bedrooms a bathroom with shower and a utility room room.

Top guest favourite
Villa
5 out of 5 average rating, 84 reviews

Church of the Vaioni

An ancient deconsecrated church dating back to the early 1900s, originally built as a private chapel of Villa Philipson. Chiesino Dei Vaioni has a loft structure with two double bedrooms on two separate mezzanines. Outside, there is a kitchen with a wood-burning oven, private gardens with a tree-lined avenue and an olive grove. The gates and internal stairs were built by the Antica Fonderia Michelucci. Chiesino Dei Vaioni is immersed in the Tuscan countryside just minutes from the city.

Top guest favourite
A charming stone chalet is surrounded by colorful autumn foliage, featuring wooden shutters and a balcony that overlooks the landscape. The vibrant leaves contrast with the earthy tones of the building, while the lush green lawn is scattered with fallen leaves.
Cabin
4.97 out of 5 average rating, 116 reviews

House with a view surrounded by nature_ 5

A cozy stone and wood chalet with amazing views of the Apennines, surrounded by nature with a large garden where you can relax and enjoy the spectacular sunsets. We will be happy to host you on the ground floor which is dedicated to the B&B. The warm and welcoming rooms have independent entrances and lead onto the garden. Fantastic location between Bologna and Florence, 10' from the motorway exit and 30' from Bologna airport. Don't miss the sunset, even better with a good glass of wine!

Top guest favourite
Home
5 out of 5 average rating, 39 reviews

Casa Bellavista

Relax with the whole family in this mountain house, surrounded by greenery. The house is located in the small village of Montefegatesi, 850 metres above sea level. It includes an entrance, a fully equipped kitchen, and a living-dining room with a panoramic view from the terrace (TV and Wi-Fi). A bathroom with a shower, a double bedroom with a terrace and a small bedroom with two beds (a cot and a changing table are available). An outdoor courtyard with a table, parasol and barbecue.

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
5 out of 5 average rating, 226 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.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment
5 out of 5 average rating, 60 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Superhost
An outdoor swimming pool is centrally located, surrounded by a stone patio and lounge chairs. Lush greenery and gently sloping hills frame the area, while distant mountains provide a scenic backdrop under a clear blue sky.
Villa
4.73 out of 5 average rating, 37 reviews

5 Star Luxury Villa Tuscany

This gated villa, with its own private road, is set in five acres of spectacular countryside; commanding breath taking views of the Serchio Valley and Apennine mountains. Villa Barsellotti offers a pocket of peace and tranquillity and is the ideal location for those seeking five-star accommodation within a rural setting. The environment permeates an aura of serenity and harmony and the area is a paradise for walkers, artists, nature enthusiasts, gourmets and adventurers.

Top guest favourite
Home
5 out of 5 average rating, 79 reviews

Experience Real Tuscany from our Country Home

An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Top guest favourite
A spacious living area is adorned with intricate frescoes and elegant decor, featuring a comfortable cream-colored sofa and a wooden coffee table. Light filters through large windows, illuminating the room’s artistic details. In the background, a cozy sleeping area with a canopy bed is visible.
Apartment
5 out of 5 average rating, 154 reviews

[SAN LORENZO-DUOMO] Prestigious Historic Residence

Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

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
4.99 out of 5 average rating, 313 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.

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