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Vacation rentals with a pool in San Gimignano

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Top-rated rentals with a pool in San Gimignano

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Top guest favorite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 109 reviews

Casa Luigi Suite with exclusive pool

Come to this apartment: you will be welcomed by centuries of tranquility, and appreciate nature and relaxation. Carefully modernized (and with a swimming pool), this space embodies the roots of good Tuscan living – an equipped olive grove consisting of a pergola with a table and bathroom, a garden with a hammock and in the shade of pine and cypress trees, with chairs, deck chairs and a rocking chair, you can admire the rolling Chianti hills. Courtyard equipped with table and chairs. There is a beautiful elevated swimming pool with some games and a barbecue In addition to the farmhouse, the property includes an olive grove of about 1 hectare, in which equipped spaces have been created for complete relaxation. The Suite has a private entrance that leads directly to the upper floor of the farmhouse, allowing maximum privacy for guests. The farmhouse is part of a small old village inhabited by 4 very discreet and friendly family units. The suite's surface area is 90 square meters and consists of a dining room with kitchenette, large living room, double bedroom, bathroom with shower and a large attic (the door is 1.2 meters wide) with 3 single beds. A very bright environment and immersed in the complete tranquility of the countryside, it is equipped with air conditioning, satellite TV, and free 24-hour Wi-Fi. The owners provide the laundry area. Uncovered private parking. The owners are happy to welcome their guests and are available to resolve any issues. The small village is inhabited by three other very kind and discreet families, ready to help the guest. Tavarnelle is 25 km from Florence, 15 km from San Gimignano, 35 km from Siena. - Images of the exterior, swimming pool, garden and equipped olive grove will be visible soon. We kindly ask you to wait. The accommodation is about 5 km from the center of Tavarnelle. The historic center is equipped with all the services for the citizen and tourist: post office, police, municipality, emergency room, supermarket, trattorias, pizzerias, banks, etc. In addition, in the summer there are various musical events, small craft markets, and finally, every Thursday morning, the classic municipal market takes place. Places of interest (medieval villages) around Tavarnelle: San Donato in Poggio about 12 km. Barberino Val d'Elsa 6 km. Distances from art cities: Tavarnelle - Florence about 25 km Tavarnelle - San Gimignano/Monteriggioni about 20 km Tavarnelle - Siena about 35 km. In the organized outdoor spaces there is an ABOVE GROUND pool, the dimensions are: 10 meters X 5 meters, with a depth of 1.20 meters. A bathroom with shower completes the pool area. In the courtyard, guests have a nice table with barbecue. The entire olive grove area is at their disposal with maximum privacy. The owners, at the guest's request, can book hiking tours or wine-testing tours with the help of professionals. The price of any tour booking is not included in the price of the stay. The small village was once a military fortress, then a parish church or place of worship and from the beginning of the 20th century inhabited by farmers. Today it is inhabited by four very nice and discreet families ready to help the guest. Florence is 15.5 miles away and Siena is 21.7 miles away

Top guest favorite
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, 324 reviews

Podere Vergianoni immerso nelChianti con piscina

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.

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 129 reviews

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.

Top guest favorite
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, 206 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 favorite
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

Belforti Tower

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.

Top guest favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 129 reviews

Private Chianti Cottage, Garden & Vineyard Views

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.

Top guest favorite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 215 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favorite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

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.

Top guest favorite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 420 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Superhost
A cozy living area features a fireplace with stacked logs, complemented by a comfortable armchair and decorative wall art. A spacious bed is visible in the background, framed by wooden beams that enhance the room's rustic charm.
Home in Tavarnelle Val di Pesa
4.87 out of 5 average rating, 198 reviews

Nada Home

My home is nestled in the Tuscan countryside, surrounded by olive trees and vineyards, in the heart of Chianti. All around, beautiful views and a peaceful, relaxing atmosphere. The garden is a special space, perfect for enjoying time outdoors. For those who wish, it is possible—upon request—to share moments of cooking and conviviality, such as carefully prepared dinners to be enjoyed together, even by candlelight, in an intimate and welcoming setting.

Top guest favorite
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, 131 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 favorite
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, 194 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.

Popular amenities for San Gimignano rentals with a pool

When is the best time to visit San Gimignano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$44,085 GYDG$46,384 GYDG$37,608 GYDG$34,683 GYDG$36,146 GYDG$39,907 GYDG$43,459 GYDG$44,294 GYDG$41,787 GYDG$38,444 GYDG$35,519 GYDG$44,294 GYD
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Quick stats about vacation rentals with a pool in San Gimignano

  • Total vacation rentals

    Explore 520 vacation rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano vacation rentals start at G$10,447 GYD per night before taxes and fees

  • Verified guest reviews

    Over 13,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    310 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    500 of San Gimignano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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

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