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Villa vacation rentals in San Gimignano

Find and book unique villas on Airbnb

Top-rated villa rentals in San Gimignano

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

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Guest favourite
A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 107 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

Top guest favourite
The exterior view showcases a charming country house complemented by lush greenery. A well-maintained garden features a winding gravel path leading to a hot tub area surrounded by elegant shades and comfortable sun loungers.
Villa in Canneto, San Miniato
4.94 out of 5 average rating, 121 reviews

Tuscany Country House Villa Claudia

La Nostra Country House è incastonata in un bellissimo Casale antico, finemente ristrutturato, panoramicissimo, costruito a margine dell'antico Borgo di Canneto, insediamento rurale nel territorio di San Miniato, risalente al 785 d.c. Il Casale, immerso nella Natura ma dotato di ogni comfort moderno, vi regalerà momenti indimenticabili, potendo scegliere tra vacanze in assoluto Relax, attività culturali (vicinissime le città d'Arte della Toscana), gustosi tour enogastronomici e tanto altro!

Guest favourite
The pool area is surrounded by meticulously maintained grass and features comfortable lounge chairs placed along the edge. A rustic wooden structure with open sides provides shade, and lush greenery is visible in the background, enhancing the serene setting.
Villa in Castiglione d'Orcia
4.97 out of 5 average rating, 123 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Superhost
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 254 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
A modern villa with a stone exterior features strategically placed windows and a prominent porch area. The surrounding greenery includes an olive tree, while steps lead to a well-maintained garden. An ornamental planter sits at the forefront, adding a decorative touch to the entrance.
Villa in Siena
4.98 out of 5 average rating, 197 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Guest favourite
An inviting indoor hot tub is highlighted, featuring sleek white surfaces and wooden accents. Two glasses of white wine and a tray of fresh raspberries are placed nearby, enhancing the relaxing ambiance of the space.
Villa in Monteroni d'Arbia
4.95 out of 5 average rating, 146 reviews

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

Top guest favourite
A charming entrance is framed by lush greenery, leading to a secluded patio area adorned with wrought iron furniture. Stone steps rise gently, with rustic arches visible overhead, creating a serene transition into the garden space.
Villa in Capannori
4.92 out of 5 average rating, 207 reviews

La Dimora Dei Conti: Indulge in a Country Farmhous

Only a Four minute drive away or 20 mins walk from the city and the Lucca train station stands La Dimora Dei Conti a superb luxury apartment located in a farmhouse villa that dates back to the 15th century and now completely and painstakingly renovated to transport you to the an era of modern beauty and traditional Tuscan feeling.<br><br>As soon as you enter the foyer you will feel the special atmosphere that permeates the villa.

Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano
4.96 out of 5 average rating, 189 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Top guest favourite
A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.
Villa in Montespertoli
4.94 out of 5 average rating, 194 reviews

Colonica nel Chianti

Splendida porzione di casa colonica immersa nel Chianti con bellissima piscina, circondata da vigne e olivi, perfettamente arredata con vasto giardino e posti macchina. Si trova a 20 minuti da Firenze, 40 da Siena e 50 da Pisa, in pochi minuti si raggiunge Certaldo (città natale di Boccaccio) e Vinci (città natale di Leonardo Da Vinci). la casa è a metà strada tra Montespertoli e San Casciano (7km).

Superhost
A private pool area is surrounded by landscaped gardens and tall trees, with several lounge chairs positioned nearby. The pool is set on a wooden platform, offering scenic views of the rolling hills in the background under a clear blue sky.
Villa in Gambassi Terme
4.84 out of 5 average rating, 155 reviews

Il Leccio - Tuscany home near San Gimignano

Tuscan farmhouse with beamed ceilings and large living area with fireplace. 3 bedrooms, 2 bathrooms and an outdoor area for lunches and dinners in the company. Hilly and windy landscape with panoramic views of the Tuscan countryside. 12 km from San Gimignano, 30 from Volterra, 30 from Siena and 2 km from the medieval village of Certaldo Alto.

Top guest favourite
A serene pool area is featured, surrounded by well-maintained greenery. Several lounge chairs are positioned along the pool's edge, inviting relaxation. The sky is clear and blue, complementing the tranquil setting of the property.
Villa in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 163 reviews

Podere Guidi

Appartamento in Villa panoramica tra Firenze e Siena, nel cuore del Chianti, in un borgo incantevole. Piscina aperta da maggio a fine settembre. Dal 2026 la piscina sarà aperta dalle ore 9 alle 13 con utilizzo esclusivo per gli ospiti in questo orario.

Popular amenities for San Gimignano villa rentals

Quick stats about villa rentals in San Gimignano

  • Total vacation rentals

    Explore 70 vacation rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano vacation rentals start at $98 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,360 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 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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  3. Tuscany
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  5. San Gimignano
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