
Vacation rentals in Gaiole in Chianti
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Top-rated vacation rentals in Gaiole in Chianti
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Popular amenities for Gaiole in Chianti vacation rentals
Other great vacation rentals in Gaiole in Chianti
Guest favourite

Home in Centro Storico
4.93 out of 5 average rating, 89 reviewsCestello Villa In Town
MicahRating, 5 stars1 week ago
Our family of six had an absolutely wonderful stay at Stefano and Alex’s place! The location was great being so close to many shops and restaurants, but what really set this place apart was the hospitality from the host and owner. From the moment we arrived until we departed, Stefano was very helpful and responsive. The first day we arrived, he helped with dinner restaurants at an AMAZING place nearby. Then, when my in-laws had a late flight on the day of checkout, Stefano did everything he could to make their additional hours comfortable. Like I said, from beginning to end, he was great! The unit itself was very comfortable for the six of us, including my wife and I, our 7 year old daughter, and three parents in their 70’s. The spiral stairs down proved to be a little tricky, but that was easy to overcome. All of the other amenities and little touches were very thoughtful, and we greatly appreciated the welcome treats and drinks. Highly recommend this lovely place!
Guest favourite

Cottage in Volterra
4.9 out of 5 average rating, 179 reviewsPodere Grignano, beautiful Tuscany
MarkRating, 5 stars3 months ago
Stefano and Roberta are two of the most absolute intrepid souls you will ever encounter. Their hospitality and generosity is without equal. Smartly appointed and expertly renovated, this exquisite example of an ancient farmhouse sits atop a stunning ridge line with vast views and expansive mountain scenery inspiring and enchanting at every turn. Right in the heart of Tuscany, this spectacular piece of the Italian wonderland does not disappoint!
Top guest favourite

Apartment in Volterra
5 out of 5 average rating, 10 reviewsMAIN Rustic apartment with exclusive view
VivianaRating, 5 stars4 months ago
Wonderful estate, very kind and helpful host. Too bad we only stayed one day!

Home in Centro Storico
4.81 out of 5 average rating, 68 reviews103 - Apartment
DanielleRating, 5 stars1 week ago
The space is very comfortable, high quality bed and bath linens. Heaters working well Excellent location. Thoughtful hostess. A little noise in the evening because it is on top of a bar.
Top guest favourite

Farm stay in Camucia
5 out of 5 average rating, 8 reviewsThe Garden of Olives | Casa Ippocastano
LukaszRating, 5 stars2 weeks ago
great place and a great host!
Superhost

Villa in Radicondoli
4.94 out of 5 average rating, 18 reviewsA Romantic Villa in the heart of Tuscany
AmandaRating, 5 stars7 months ago
We are 2 couples in our early 60s. We adored the home. The surrounds and views sublime. We cooked and loved sitting in kitchen as sun set. Ahhhh. We enjoyed a drink in village at a little store. Our favourite meal was at Nazionale (book or you won’t get in). The lady there is areal character you will get to like her. The agricento restaurant also good. Coop had groceries. The village of Radicondolli is just beautiful. We drove to many places from there. Siena, san Gin, the Terma Antica ….. ( warm mineral waters with spa) nice to be spoilt. Try the other small villages around Radicondoli, we did better than larger ones, like castle d’elsa. Fabulous museum. Our hosts Francesca and Lorenzo were welcoming and met us on arrival. Each room was well separated with ensuite each room. Kitchen fully appointed. Italian coffee pot (buy you ground coffee at coop in town), some basic condiments. Roomy showers, one bath, lots of room to spread out. Herbs in garden.
Guest favourite

Villa in Asciano
4.95 out of 5 average rating, 76 reviewsPodere on the Crete Senesi
ChulaRating, 5 stars6 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.

Villa in Castiglion Fiorentino
4.74 out of 5 average rating, 31 reviewsBorgo San Pietro in Polvano (Rectory)
LorenzoRating, 5 stars20 months ago
The accommodation is spacious, with 3 double bedrooms and a sofa bed, and each bedroom has a private bathroom (very large). The kitchen is well equipped with all the necessary utensils including dishes, cutlery, glasses, wine glasses, dishwasher, moka and Krups machine with pods, which make the stay even more comfortable. Laura is a very helpful person and prepared to offer information about the points of interest around the property. I highly recommend this property and we do not exclude the possibility of returning in the future!
Quick stats about vacation rentals in Gaiole in Chianti
Total rentals
30 properties
Nightly prices starting at
$83 CAD before taxes and fees
Total number of reviews
640 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Piazza della Repubblica
- Stadio Artemio Franchi
- Pitti Palace
- Mercato Centrale
- The Boboli Gardens
- Pinocchio Park
- Cavallino Matto
- Teatro Tuscanyhall
- Teatro Verdi
- Palazzo Vecchio
- Basilica di Santa Croce
- Santa Maria della Scala