
Holiday Homes in San Gimignano
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Top-rated Holiday Homes in San Gimignano
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Podere La Castellina - No. 2 LECCETO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

San Gimignano, Montagongolfi SIX
Wonderful apartment in the country side of San Gimignano, at about 3Km and 5min from town center by car, far from noise, but close to all you may need. The apartment is suited for 4 people with 2 bedrooms each one with its en-suite bathroom. Bedrooms have an high privacy, splitted by the living room with kitchen, featured by the huge fireplace where our ancient farmer used to sleep over a FIAT 500 seat. First floor, 20 steps, no elevator. Side view on San Gimignano city and towers on the right

Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Ponte Vecchio Newly restyled flat, Walk Everywhere
Cozy and bright 55 sqm apartment, just 1 minute walk from the famed and gorgeous "Ponte Vecchio". The apartment boasts a fully equipped modern kitchen and bathroom. Located in the historic center, you can easily reach Piazza della Signoria with a 5 minute walk, and "Palazzo Pitti" and the "Uffizi" Gallery in 4 minutes. The apartment is located on the 5th floor of the building. There is a lift however there are a few steps before it. Ideal for 2 guests but can fit 4.

Casa al Gianni - Oak
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

SMN Luxury Secret Garden View
Welcome to the central part of Florentine charm! This extraordinary apartment, located just 50 meters from Piazza Santa Maria Novella, offers you an unparalleled experience in the historic heart of Florence. Imagine crossing the threshold of a Renaissance Palace, a jewel of inestimable artistic and historical value, and being welcomed by an atmosphere that speaks of history and elegance. Two bedrooms, two complete bathrooms, living room with fully equipped kitchen.

Charming farmhouse with garden, views & pool
Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
Popular amenities for San Gimignano holiday homes
Family-Friendly holiday homes

Lo Scrigno Dei Sogni San Gimignano Apartment

Apartment in historic Villa in Siena_"LE CONTRADE"

Private garden overlooking the Via Francigena

Large Apartment with Pool

★ Romantic apartment & stunning view of Tuscany ★

Fienile Santa Teresa

La Dimora del Lago - Lake views of Tuscany and Umbria

Apartment La Roccaia
Holiday home rentals with a patio

The Eagle and the Olive Tree

Third floor 1

Palazzo Della Nave - AP 06

Casa Camelia - Your authentic Tuscan getaway

Noce Holiday Home @ Poderino il Sole, Tuscany

La Selva , Country house, 130 mq, Stunning views

Sunset_ by_ Bina

Elegant farmhouse overlooking Pienza
Holiday home rentals with a washing machine and dryer

La Faggiola - Cozy Studio in The Heart of Pisa

Melarancio Residence

Tuscan Nature Views From Casa Gave

[Florence Hills] Tuscan house with parking space

Podere Docciolino Vacation Home

The Cypress Terrace, stone studio & valley view

4BR • Luxury Palazzo • Iconic Views • Pitti Palace

Entire historic villa with private pool in Tuscany
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $190 NZD | $192 NZD | $278 NZD | $249 NZD | $228 NZD | $259 NZD | $280 NZD | $304 NZD | $302 NZD | $242 NZD | $187 NZD | $304 NZD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- Pet-friendly rentals San Gimignano
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- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Spiagge Bianche
- Piazzale Michelangelo
- Parco delle Cascine
- Gulf of Baratti
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio
- Things to do San Gimignano
- Food and drink San Gimignano
- Nature and outdoors San Gimignano
- Tours San Gimignano
- Things to do Siena
- Nature and outdoors Siena
- Food and drink Siena
- Tours Siena
- Art and culture Siena
- Sports activities Siena
- Sightseeing Siena
- Things to do Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Food and drink Tuscany
- Nature and outdoors Tuscany
- Sightseeing Tuscany
- Sports activities Tuscany
- Things to do Italy
- Sports activities Italy
- Nature and outdoors Italy
- Sightseeing Italy
- Wellness Italy
- Food and drink Italy
- Tours Italy
- Entertainment Italy
- Art and culture Italy







