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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Cottages in Chianti Region and around

Panorama Nest - Countryside charm with private pool
Outdoor dining

Panorama Nest - Countryside charm with private pool

10.0 out of 10, Exceptional, (1)
"Hallo , Liebe Leser, nachdem wir die ca. 600m holprige, steinige Straße hinter uns hatten, sahen wir die Unterkunft. Wir hatten 10 wunderschöne Tage in der Toskana und dem schönen Panorama Nest mit unserem Hund. Ruhig gelegen und nur ca. 6 km von Einkaufsmöglichkeiten entfernt. Alles, Perfekt, Sauber, eingezäuntes Grundstück, gut, wenn man mit Hund kommt. Der Ausblick von der Terrasse ist Traumhaft. Auch das Schwimmbad erfüllt seinen Zweck auch wenn es nicht so groß ist, hatten wir viel Spaß....
Panorama Nest - Countryside charm with private pool
Apartment/ flat - Barberino val d'ElsaHouse with character
Pool

Apartment/ flat - Barberino val d'ElsaHouse with character

9.8 out of 10, Exceptional, (39)
"We had a lovely 12 day stay in this charming little villa near Tuscany. Loretta was a wonderful host and the location was perfect for us. We enjoyed exploring Sienna, Florence and nearby Poggibonsi, but days in the pool at the villa were hard to beat (especially with the 40 degree heat)."
Apartment/ flat - Barberino val d'ElsaHouse with character
Stone cottage on heritage Chianti estate-pool-tennis
Pool

Stone cottage on heritage Chianti estate-pool-tennis

Stone cottage on heritage Chianti estate-pool-tennis
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Exterior

Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.

9.0 out of 10, Wonderful, (19)
"It was wonderful "
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Casa il Cipresso, in the heart of Chianti with swimming pool
Pool

Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Charming Farmhouse with Private Pool among Vineyards
Aerial view

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"This property is fantastic if you want to enjoy the real Tuscan life. The Villa, pool is all that is advertised. Olivia is the property manager and makes your stay everything you could hope for. We spent an entire month with 6 guests per week. Morning day trips afternoons by the pool and evenings watching the sunset with the estates wines. It was a month to remember. Cheers Steve Enna"
Charming Farmhouse with Private Pool among Vineyards
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Terrace/patio

Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

10.0 out of 10, Exceptional, (1)
"This was by far the best experience I have EVER had at a VRBO property. The house is absolutely precious and my group of four loved it. Everything was so charming- we kept comparing it to Cameron Diaz in The Holiday. The back porch is perfect for a morning cup of coffee that Eva provides (every single option) or a fabulous glass of wine at the end of the day touring vineyards in Tuscany. We can’t speak more highly about the host, Eva. She was so easy to work with, gave us fabulous restaurant...
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Casa Belvedere cottage with swimming pool in the heart of Chianti
Pool

Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Typical country house with garden near Florence Siena Pisa San Gimignano
Outdoor dining

Typical country house with garden near Florence Siena Pisa San Gimignano

9.8 out of 10, Exceptional, (47)
"Distant views of olive groves and vineyards. Misty cool mornings, listening to church bells and birdsong. THIS was our home base in Tuscany that we were lucky enough to have discovered. All of the photos and descriptions do not do justice to this beautiful villa 30 minutes outside of Florence! Close to the tram, which brought us into Florence 4 times during our incredible 2 week stay we also took advantage of our rented car to drive the beautiful scenic roads to nearby medieval villages and...
Typical country house with garden near Florence Siena Pisa San Gimignano
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Pool

Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

8.4 out of 10, Very good, (10)
"The property's location is much more remote than advertised.. We booked it as we were attending a wedding close to Gaiole and the property description says "15 minutes from Gaiole". The 2.5 km forest road took at least 10 min to get to the main road and from there it's a minimum of 20 min to Gaiole ( if you drive Italian style). No taxi or transportation company will go to the property, so forget having a drink somewhere in town. Also, no wifi at the property and the cellular reception is also...
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
La Misura, cottage with garden and swimming pool on the hills of Chianti
Outdoor dining

La Misura, cottage with garden and swimming pool on the hills of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful couple days at La Misura. Niccolò was super nice and helped us get settled. The view was like a painting of Tuscany. It was everything we could have wanted. This is a beautiful location. We will go back soon. Thank you!"
La Misura, cottage with garden and swimming pool on the hills of Chianti
La Chiantinelle - La Grange
Property grounds

La Chiantinelle - La Grange

La Chiantinelle - La Grange
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Fridge, oven, stovetop, dishwasher

La Quercia, apartment with garden for 6/8 people in the heart of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Casa Antico Roseto - cottage with swimming pool
Dining

Casa Antico Roseto - cottage with swimming pool

8.0 out of 10, Very good, (1)
"The villa is lovely. The property is amazing. Check-in and out were easy and the owners are very kind. The only complaint we really had with our stay was that it is probably not the best place to stay during the summer months when it is 95+ outside. The villa has no air conditioning and even the fans they provided us did not prepare us for the heat inside even late at night. When we opened the windows we had a lot of mosquitoes and other bugs enter the house so we were forced to close up most of...
Casa Antico Roseto - cottage with swimming pool
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Pool

Exceptionally pretty cottage with pool, views, in walking distance from Panzano

10.0 out of 10, Exceptional, (43)
"Could not have asked for more the grounds, the house, the hostess, the surroundings . . . All just beautiful and wonderful. Felt like I could have spent a month there. The hostess was so nice and so helpful. On the last night we had the chef and owner from a local restaurant, Mimo come and cook for us. It was like a movie. He was such a good cook, so nice. Sat down and talked to us and had a glass of wine . . . It was wonderful, felt like we had a much better understanding of Italy."
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Outdoor dining

Cottage "Podere in Volpaia" with Garden & Wi-Fi

10.0 out of 10, Exceptional, (3)
"Nous avons séjourné 10 jours dans cette charmante maison en Août 2023. Cristina nous a bien accueillie, la maison est très fonctionnelle, Il y a une belle terrasse couverte et un petit coin de verdure privé. La maison est entourée de vignes et d'oliviers, nous avons pu déguster l'huile et le chianti produits sur place. Cristina, la propriétaire, nous a organisé un repas et nous a fait déguster les vins de sa production. Le petit village de Radda est à 10 min en voiture, on y trouve tout ce...
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
View from property

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

9.2 out of 10, Wonderful, (7)
"Country setting with beautiful views. Low key and a good place to unplug. Good restaurants and villages near by. Simon was helpful and we enjoyed our stay."
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Villa Gaia
Property grounds

Villa Gaia

Villa Gaia
Belvilla by OYO Cottage in Tavarnelle With Garden
Cottage | Pool

Belvilla by OYO Cottage in Tavarnelle With Garden

Belvilla by OYO Cottage in Tavarnelle With Garden
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Exterior

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chianti Region

Relais Villa Olmo
Aerial view

Relais Villa Olmo

9.4 out of 10, Exceptional, (201)
"My family and I stayed there for 2 nights, at the family suite. It was very clean and well decorated & furnished, with private pool and garden. The environment and view were good, staff were helpful, buffet breakfast got lot of choices. Highly recommended this lovely place "
The price is €88
includes taxes & fees
13 Mar - 14 Mar
Relais Villa Olmo
Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
Holiday home in the Florentine Chianti half an hour from Florence
Interior

Holiday home in the Florentine Chianti half an hour from Florence

9.8 out of 10, Exceptional, (53)
"My wife and I spent nine nights is this spacious and well-equipped home in the quiet village of Montespertoli in the Chianti region of Tuscany. Bruno was a wonderful host, always quick to respond to our questions. He left the home equipped well for our first night or two and directed us to the Co-Op grocery store only a 3-4 minute walk from the front door. Our rental car was securely parked in his garage every night, so no need to park on the street or worry about not finding a place close to...
Holiday home in the Florentine Chianti half an hour from Florence
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.