Vacation rentals with a patio in Gaiole in Chianti

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Top-rated patio rentals in Gaiole in Chianti

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Guest favorite

Apartment in Sinalunga

4.98 out of 5 average rating, 120 reviews

Canale Suite - panoramic view - free parking

Villa tipica Toscana con vista panoramica . Posto strategico per visitare le località famose Toscane e Umbre . A 5 minuti dal Casello Autostradale A1 , la villa ha parcheggio privato gratuito . Camere nuove con bagno privato , cucina , frigorifero , SMART TV , potente Wi-Fi , Aria Condizionata , biancheria di alto livello , acqua , tea , caffè gratuiti . Luogo accessibile ad auto e furgoni , immerso nel verde a meno di 1 km dal centro del paese , bar , ristoranti e supermercati sempre aperti.

Sep 25 – Oct 2

G$16,373 GYD per night

Guest favorite

Tower in San Quirico d'Orcia

5.0 out of 5 average rating, 43 reviews

Luxurious Medieval Tower & Private Concierge

It's rare to find a place that's not only romantic, but also historic and truly one of a kind. “La Torretta” is part of “Toscana a Due” - a medieval tower with a huge garden and olive trees and one of the two only towers left in the village. Over the last years the historic building has been refurbished in order to design a space that is both historic and luxurious. Additionally, we offer a private concierge service, in order for you to discover the authentic Tuscany and its hidden treasures!

Nov 10 – 17

G$56,512 GYD per night

Guest favorite

Condo in Monte San Savino

4.93 out of 5 average rating, 27 reviews

Rural Tuscany | Agriturismo with restaurant & pool

Agriturismo la Foresteria is situated in an ancient rural village between the Tuscan towns of Cortona and Montepulciano, in the southeast of Tuscany. The farm is owned by the Illuminati family that carries out its activity in the field of fruit and vegetable cultivation. The estate is wonderfully surrounded by an enchanting natural landscape that, with the lush surrounding countryside and the cultivation of fruit trees, gives guests staying there a feeling of serenity and unique peace.

Mar 11 – 18

G$22,028 GYD per night

Guest favorite

Home in Poggibonsi (San Martino)

5.0 out of 5 average rating, 25 reviews

Agriturismo Podere San Martino (apartment for two)

Piccolo appartamento di circa 40 mq a San Martino ai colli, situato lungo la via Cassia e circondato dalla bella campagna toscana. Perfetto per chi ha voglia di rilassarsi, assaggiare prodotti del luogo (olio, miele and zafferano) e visitare le attrazioni della zona: San Gimignano, Monteriggioni, Chianti, Siena (20 min.), Firenze (30 min.), Volterra (40 min.). A due minuti dal raccordo autostradale Firenze- Siena e vicino al centro urbano di Poggibonsi e di Barberino-Tavarnelle.

Feb 20 – 27

G$13,335 GYD per night

Guest favorite

Home in Barberino Tavarnelle

5.0 out of 5 average rating, 24 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Podere Tignano is located on the gentle green hills of Chianti between Florence and Siena, Podere Tignano enjoys stunning views of the countryside surrounding with grain fields, vineyards and olive groves. The villa has been restored preserving the original characteristics of its Tuscan stone structure harmoniously divided in two levels. The villa is 180 square meters and can accommodate 8 persons in 4 bedrooms with 3 bathrooms. Private pool for the exclusive use of the guests.

Nov 18 – 25

G$82,199 GYD per night

Guest favorite

Home in Gambassi Terme

4.99 out of 5 average rating, 113 reviews

Il Fienile, luxury apartment on Tuscan hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breath-taking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, only 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.

Dec 11 – 18

G$41,145 GYD per night

Guest favorite

Condo in Montefioralle

4.93 out of 5 average rating, 58 reviews

Peaceful hideaway in a 11th century Tuscan village

Imagine a former medieval tower, once part of a 11th century fortified castle. As you enter, like in most Tuscan country houses, there is a kitchen with a stone sink. A stairway brings to the first floor where there are two bedrooms with their original terracotta floors and wooden beams. They both offer a gorgeus, unobstructed view of Chianti vineyards and hills. And a private access to a terracotta terrace facing the valley. It's hard to imagine a more peaceful scenery.

Mar 21 – 28

G$41,240 GYD per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 13 reviews

Tuscany on the terrace, Montepulciano Centro

Welcome to Montepulciano, the hidden jewel of Tuscany, where the historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region. Immersed in the evocative labyrinth of stone-paved streets, you will be greeted by the reassuring sound of the bell towers announcing the passage of time, while the inviting scent of freshly baked bread mixes with the aromatic notes of our vineyards.

Apr 19 – 26

G$32,369 GYD per night

Guest favorite

Condo in Pienza

5.0 out of 5 average rating, 54 reviews

Mascagni Farmhouse in Val d 'Orcia Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 1500-year-old barn nestled amid olive and wheat fields. Unwind with a cup of tea, pick rosemary, and lavender in the garden with breathtaking views of Val d 'Orcia. Re-discover your true nature among the pristine fields and olive trees - there are no boundaries for walks and bike rides here! Ready to create memories that will last a lifetime?

Oct 30 – Nov 6

G$44,487 GYD per night

Guest favorite

Home in Montebenichi

5.0 out of 5 average rating, 30 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

Spacious and rustic apartment with terrace with 360-degree views of the entire Tuscan hillside in a period building. The apartment consists of 2 spacious bedrooms, 1 large bathroom, 1 fully equipped kitchen and 1 charming living room. Strategically located, a few minutes from our private swimming pool surrounded by olive groves and in the middle between Val D'Orcia and Chianti. The apartment is renovated and located in the beautiful historic village.

Sep 17 – 24

G$92,959 GYD per night

Guest favorite

Vacation home in Rosennano

5.0 out of 5 average rating, 32 reviews

HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL

The apartment Il Nido is located on the second floor of a stone building, beautifully renovated a few years ago, which is located in the charming village of Rosennano. It is the ideal solution for a couple with children (up to four) or for friends who love nature and tranquillity. From the rooms and the beautiful Loggia you can enjoy a magnificent view of the Tuscan countryside, the shared garden and the swimming pool to which guests have easy access.

Mar 11 – 18

G$37,238 GYD per night

Guest favorite

Vacation home in Gaiole in Chianti

4.92 out of 5 average rating, 13 reviews

The Piccola Villa of Borgo Argenina

Piccola Villa is a cozy small house, excellent choice for 2\3 person, decorated in traditional Tuscan style with hand-made quilts and antique furniture. The villa has private garden where you can admire beautiful old roses and breathtaking views of the historical vineyards and olive groves. Well-equipped with garden furniture for comfortable meals outside, guests can enjoy the fresh Chianti breeze and the breathtaking views of the vineyards.

Aug 10 – 17

G$75,664 GYD per night