
Holiday houses in Castel San Gimignano
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Top-rated holiday rentals in Castel San Gimignano
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Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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.

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.”

"Landscape Notes" Suite
The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Authentic Tuscany Experience in Our Country House
An amazing experience between nature, flavor 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 olive groves and vineyards 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.

Casa Titta, Tuscany around you
Casa Titta is one of the 4 apartments in the "La Casina di Manu" complex. It is located in Castel San Gimignano, a small village in the heart of Tuscany, in a strategic position both to be able to visit some of the most important centers of our region (San Gimignano, Volterra, Siena and Florence) and to be able to take routes on foot or by bicycle, immersed in an enchanted landscape, dotted with olive groves, vineyards and cypresses.

Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

ECOLOGICAL FARMHOUSE "THE OLD OAKS"
A big apartment consisting of a kitchen and dining room at the entrance; from here you climb to the upper floor where there is a livingroom with sofa and two armchairs, a TV equipped with a DVD player. From the living room a corridor leads to a first double bedroom with private bathroom, followed by a small hallway serving two other double bedrooms with a common bathroom.

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.

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Girasole large apartment in a Tuscan village
Cozy and spacious apartment in a small Tuscan village in the municipality of San Gimignano. Casa Girasole is located in Castel San Gimignano, a small and ancient village which is 12 km from San Gimignano, 15 km from Volterra, 30 km from Siena and 50 km from Florence and 50 km from the Tyrrhenian Sea.
Popular amenities for Castel San Gimignano holiday rentals
Other great holiday rentals in Castel San Gimignano

Luxury Medieval Tower - Penthouse

NiKKO 119 [Loft Deluxe With Garden City Center]

Rosa: Tuscan Views & Pool, Walk to Town

Romantic Villa with private pool - "Il Pollaio"

Luxury Penthouse with a View of Piazza del Campo

Rustic Cavernous by Interhome

Fabulous 3Br Villa with 360° Views!

Luxury Apartment in the Historic Centre of Siena
Destinations to explore
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Uffizi Gallery
- Mugello Circuit
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Parco delle Cascine
- Gulf of Baratti
- Basilica of Santa Croce
- Medici Chapel





