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Vacation rentals in San Gemignano

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in San Gemignano

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

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Top guest favorite
Townhouse in Scandicci
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 favorite
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 in Bagni di Lucca
4.95 out of 5 average rating, 63 reviews

Infinity pool Pisa-Lucca-Florence Uitzicht rondom

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 favorite
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 in Monzuno
4.97 out of 5 average rating, 116 reviews

Casa con vista immersa nella natura_ 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 favorite
Home in Montefegatesi
5.0 out of 5 average rating, 39 reviews

Casa Bellavista

Rilassati con tutta la famiglia in questa casa di montagna, immersa nel verde. La casa è situata all' interno del piccolo borgo di Montefegatesi a 850 metri sopra il livello del mare. Comprende un ingresso, una cucina con tutte le comodità, un salotto - sala da pranzo con vista panoramica dal terrazzo (TV e Wi-Fi). Un bagno con doccia, una camera matrimoniale con terrazzo e una camerina con due letti (culla e fasciatoio a disposizione). Un aia esterna, con tavolo, ombrellone e barbecue.

Top guest favorite
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
5.0 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.

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 in Bagni di Lucca
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 favorite
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.
Condo in San Gimignano
5.0 out of 5 average rating, 59 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.”

Top guest favorite
Villa in Pistoia
5.0 out of 5 average rating, 84 reviews

Chiesino Dei Vaioni

Antica chiesa sconsacrata risalente ai primi del 900, originariamente costruita come cappella privata di Villa Philipson. Chiesino Dei Vaioni ha una struttura a loft con due camere matrimoniali su due soppalchi distinti. All’esterno cucina con forno a legna, giardini privato con viale alberato ed oliveto. I cancelli e le scale interne furono costruiti dalla Antica Fonderia Michelucci. Chiesino Dei Vaioni è immerso nella campagna toscana a pochi minuti dalla città.

Guest favorite
Castle in Tignano
5.0 out of 5 average rating, 24 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top guest favorite
Home in Barberino Tavarnelle
5.0 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.

Luxe
An infinity pool is set against a backdrop of lush greenery, with comfortable seating options placed nearby. Soft lighting creates a serene atmosphere as the landscape gently slopes away, revealing hills in the distance under a twilight sky.
Villa in Lucca
4.94 out of 5 average rating, 32 reviews

Villa Lina, Luxury Farmhouse with Pool and Amazing

Lush vegetation invites you to surround to huge stretches of verdant woods. Extensive views towards the city of Lucca and the Tuscan rolling hills on the back are ready to embrace you during lazy summer days. Time can be stopped at Villa Lina, and you will easy forget your busy life left behind. If Stendhal syndrome is known to develop when encountering something overwhelmingly beautiful, then be careful, as you could be subject to it at this magic place.

Guest favorite
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, 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.

Popular amenities for San Gemignano vacation rentals