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Holiday rentals with a pool in San Gimignano

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Gimignano

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 289 reviews

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.

Top Guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 204 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Top Guest favourite
A spacious living area is furnished with a dining table and four chairs, complemented by a cozy sofa. Large windows offer views of the surrounding landscape, while subtle natural light filters through textured shades. A television is mounted on the wall, with a glimpse of an elegant bathroom in the background.
Loft in Scandicci
4.98 out of 5 average rating, 125 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top Guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 124 reviews

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.

Top Guest favourite
A set of large wooden wine barrels features a prominent yellow sign with the name 'Panzanello.' The barrels are positioned on a stone surface, surrounded by a serene landscape under a partially cloudy sky.
Condo in Panzano
4.96 out of 5 average rating, 259 reviews

Apt.Panzanello-Panzano in Chianti

L'appartamento offre tutte le comodità e la tranquillità della campagna Toscana. Godetevi il meraviglioso panorama che potrete ammirare dalla vostra terrazza privata, luogo perfetto dove trascorrere attimi di pace e serenità e accompagnati da un buon bicchiere di vino Panzanello. L'accesso all'appartamento è privato ed è disponibile il parcheggio gratuito. La cucina è attrezzata con l'occorrente per preparare deliziosi pasti.

Top Guest favourite
Farm stay in Pisa
4.99 out of 5 average rating, 311 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Top Guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 179 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Superhost
A warm and inviting fireplace is surrounded by various decorative elements, including potted plants and wall art. Baskets filled with logs are neatly arranged, enhancing the cozy ambiance. Natural light enters through nearby windows, creating a bright and comfortable space.
Home in Tavarnelle Val di Pesa
4.9 out of 5 average rating, 172 reviews

Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

Guest favourite
The entrance of the rustic stone building is framed by flowering plants in terracotta pots. A wooden door provides access, while a wall-mounted lamp illuminates the area. A small window adds to the charm, showcasing the textured surface of the building.
Home in Barberino Val d'Elsa
4.96 out of 5 average rating, 142 reviews

La Colombaia Farmhouse

The apartment has its own entrance , large living room with well equipped kitchen , 3 bedrooms and 2 bathrooms. It has a private garden with BBQ and gazebo , which offers a beautiful view of Vico d' Elsa , San Gimignano and the sunset. Swimming pool from 23/04 to 31/10.

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, 164 reviews

Podere Guidi

Apartment in a panoramic villa between Florence and Siena, in the heart of Chianti, in a charming village. Pool open from May until the end of September. From 2026, the pool will be open from 9 am to 1 pm with exclusive use for guests during this time.

Guest favourite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Condo in San Gimignano
4.95 out of 5 average rating, 139 reviews

Adalberto Apartment inside the Manor of Fulignano

Nella campagna di San Gimignano, in antica fortificazione risalente all'anno 1000 ora dimora di campagna, situata su di un colle con veduta panoramica, affittasi bellissimo appartamento di ca. 60mq con vista su San Gimignano e sui vigneti circostanti

Popular amenities for San Gimignano rentals with a pool

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Avg. price$255 AUD$264 AUD$249 AUD$255 AUD$266 AUD$293 AUD$320 AUD$326 AUD$307 AUD$233 AUD$223 AUD$257 AUD
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Quick stats about holiday rentals with a pool in San Gimignano

  • Total holiday rentals

    Explore 550 holiday rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano holiday rentals start at $15 AUD per night before taxes and fees

  • Verified guest reviews

    Over 13,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 240 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    540 of San Gimignano holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across San Gimignano rentals

  • 4.7 Average rating

    San Gimignano stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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