Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Chianti Region vacation rentals

Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
$229 nightly
The price is $257
Jun 30 - Jul 1
Total with taxes and fees
Villa il Fedino
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (246 reviews)
$139 nightly
The price is $156
Jul 12 - Jul 13
Total with taxes and fees
Relais Villa Olmo
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
$160 nightly
The price is $175
Jul 5 - Jul 6
Total with taxes and fees
Villa di Sotto
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
$313 nightly
The price is $348
Jun 24 - Jun 25
Total with taxes and fees
Terre di Baccio
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$231 nightly
The price is $256
Jun 29 - Jun 30
Total with taxes and fees
Riserva di Fizzano Residence
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
$305 nightly
The price is $345
Jun 23 - Jun 24
Total with taxes and fees
Borgo Argenina
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
$146 nightly
The price is $163
Jul 10 - Jul 11
Total with taxes and fees
Palazzo Pacini
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (68 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
$159 nightly
The price is $185
Jun 23 - Jun 24
Total with taxes and fees
Villa Curina Resort
Garden view

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
$74 nightly
The price is $88
Jun 26 - Jun 27
Total with taxes and fees
Villa San Filippo
Exterior

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
$103 nightly
The price is $118
Jun 28 - Jun 29
Total with taxes and fees
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$73 nightly
The price is $82
Jun 29 - Jun 30
Total with taxes and fees
Chianti Village Morrocco
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
$126 nightly
The price is $143
Jul 6 - Jul 7
Total with taxes and fees
B&B La Fonte del Machiavelli
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$136 nightly
The price is $149
Jun 22 - Jun 23
Total with taxes and fees
Villa Cassia di Baccano
Front of property

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
$176 nightly
The price is $194
Jun 28 - Jun 29
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
Panoramic Apartment | 2 bedrooms, Frette Italian sheets, hypo-allergenic bedding

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (33 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
$92 nightly
The price is $104
Jul 5 - Jul 6
Total with taxes and fees
Residence Il Connubio
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
$85 nightly
The price is $98
Jun 25 - Jun 26
Total with taxes and fees
Mariani Bed & Breakfast
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
$58 nightly
The price is $67
Jun 22 - Jun 23
Total with taxes and fees
Hu Norcenni Girasole Village
Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.6 out of 10, Exceptional, (5 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
$142 nightly
The price is $159
Jun 22 - Jun 23
Total with taxes and fees
Casa Vacanze Le Fornaci
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (83 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$145 nightly
The price is $165
Jun 30 - Jul 1
Total with taxes and fees
Antico Borgo il Cardino
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (63 reviews)
"Very friendly staff. Great breakfast! In alla very nice!"
Sweden
martin
$71 nightly
The price is $83
Jun 24 - Jun 25
Total with taxes and fees
Villa Il Palagio
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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Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"My husband and I recently stayed at this beautiful resort and spa to celebrate our 46th wedding anniversary, and it was truly a memorable experience from beginning to end. The staff was exceptionally kind, welcoming, and helpful, making us feel valued throughout our stay. The food was absolutely delicious, with every meal exceeding our expectations. One of the highlights of our visit was the relaxing couple's massage, which left us feeling refreshed and rejuvenated. The resort amenities were wonderful and thoughtfully maintained, providing everything needed for a peaceful and enjoyable getaway. The views were simply magnificent, and each evening we were captivated by the mesmerizing sunsets that painted the sky with stunning colors. We also enjoyed exploring the nearby town, which was charming and beautiful. Between the breathtaking scenery, outstanding service, luxurious amenities, and tranquil atmosphere, our anniversary celebration was everything we had hoped for and more. We highly recommend this resort and spa to anyone looking for a relaxing and unforgettable escape. We look forward to returning again someday."
Maria 5-night trip
Posted 21 hours ago
Villa I Barronci Resort & Spa

Find out more about Chianti Region

Everything you need to know about Chianti Region vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chianti Region vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chianti Region vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chianti Region in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $57 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chianti Region rentals

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