
House vacation rentals in San Gimignano
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Top-rated house rentals in San Gimignano
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Casa al Gianni - The Simignano Barn
Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Garden House
"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

House for the Coast
In the center, a completely renovated, cozy and quiet historic house from the 1300s, equipped with every comfort. Independent entrance, kitchen, living room and bathroom and upstairs double bedroom and bathroom. Located 100 meters from Piazza Arnolfo and 200 meters from the historic center, for those traveling by bus the stop is just 200 meters away. Convenient location for visiting Siena, Florence, San Gimignano, Volterra, Chianti and for walking the Via Francigena or taking the Elsa Trail.

House with a breathless view in Tuscany
Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

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.

StageROOM03 - Idyllic Chianti cottage near Siena
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Casa Maurino
"Casa Maurino", in the historic center of San Gimignano, is a delightful apartment nestled in the ancient city walls. Ideal place to spend short stays, immersing yourself in the evocative atmosphere of the medieval village. Located in a quiet and peaceful position with a panoramic terrace overlooking the Tuscan hills to indulge in romantic moments of relaxation. Independent entrance from a characteristic stone staircase, panoramic terrace. Suitable for couples.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

"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 Gimignano house rentals
House rentals with a pool

dependance in villa Toscana

Casa Bada - Barn

Casetta Melograno – Cozy farmhouse in Chianti

Collina Power

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool

Lovely house in a scenic and paiceful location
Weekly house rentals

Love in Chianti

The Roses of Montagnana

Fabulous farmhouse in the Chianti area with panoramic garden

Casa La Selva

Historic house in heart of Tuscany

A Tuscan Countryside Hideaway with Panoramic Views

House in Tuscany: San Gimignano view

"The Winery"
Private house rentals

Historical Palace 13° century San Gimignano

House "Il Campanile"

Entire home in San Gimignano

Villa in the Hills - San Martino *Chianti*

ViaVecchia San Gimignano:pool, garden, parking

Casa Bonelli

Agriturismo Podere San Martino (apartment for two)

"Zafferano" of Podere la Fonte
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $229 CAD | $202 CAD | $163 CAD | $212 CAD | $206 CAD | $233 CAD | $249 CAD | $238 CAD | $234 CAD | $201 CAD | $165 CAD | $235 CAD |
| 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 |
Quick stats about house rentals in San Gimignano

Total vacation rentals
Explore 150 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at $14 CAD per night before taxes and fees

Verified guest reviews
Over 3,950 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
140 of San Gimignano vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across San Gimignano rentals

4.8 Average rating
San Gimignano stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- House rentals Siena
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- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Spiagge bianche
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Spiaggia Libera
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
- Things to do San Gimignano
- Nature and outdoors San Gimignano
- Food and drink San Gimignano
- Things to do Siena
- Sightseeing Siena
- Tours Siena
- Nature and outdoors Siena
- Food and drink Siena
- Art and culture Siena
- Sports activities Siena
- Things to do Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Things to do Italy
- Food and drink Italy
- Tours Italy
- Wellness Italy
- Sightseeing Italy
- Sports activities Italy
- Art and culture Italy
- Nature and outdoors Italy
- Entertainment Italy






