Gaiole in Chianti Villas from CA $194

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti villas

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi

Gaiole in Chianti

CA $385 total

includes taxes & fees

Jun 30 - Jul 1

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "

Ravin N.

CA $2,740 total

includes taxes & fees

Jun 29 - Jun 30

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

CA $2,484 total

includes taxes & fees

Jun 28 - Jun 29

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

Alvaro

CA $287 total

includes taxes & fees

Jul 1 - Jul 2

Luxury Villa in the Florentine hills

Florence

edward p.

CA $544 total

includes taxes & fees

Jun 29 - Jun 30

Villa Marcolina

Castelnuovo Berardenga

CA $1,249 total

includes taxes & fees

Jun 30 - Jul 1

Il Poggio dell'Eremita

Sinalunga

Paul Q.

CA $253 total

includes taxes & fees

Jul 4 - Jul 5

Exclusive Estate in Florence, Private Pool, 13 bedrooms

Oltrarno

Molly M.

CA $11,354 total

includes taxes & fees

Jul 27 - Jul 28

Rooster House, cooking classes and opera

Toscana

CA $194 total

includes taxes & fees

Jul 5 - Jul 6

Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $733 total

includes taxes & fees

Jun 28 - Jun 29

VILLA IL MATTO with salt pool, with spa and sauna

Toscana

CA $724 total

includes taxes & fees

Jun 29 - Jun 30

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Rignano sull'Arno

CA $805 total

includes taxes & fees

Jul 5 - Jul 6

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Impruneta

Maria H.

CA $646 total

includes taxes & fees

Jun 28 - Jun 29

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

CA $9,573 total

includes taxes & fees

Jun 28 - Jun 29

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Murlo

"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...

martina p.

CA $4,615 total

includes taxes & fees

Jul 14 - Jul 15

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Saltino

CA $1,387 total

includes taxes & fees

Jun 30 - Jul 1

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

CA $684 total

includes taxes & fees

Jun 28 - Jun 29

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

CA $8,423 total

includes taxes & fees

Jun 28 - Jun 29

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

Rignano sull'Arno

CA $986 total

includes taxes & fees

Jul 10 - Jul 11

Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $3,130 total

includes taxes & fees

Jul 26 - Jul 27

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Top Gaiole in Chianti Hotel Reviews

Hotel Italia

10/10 Excellent

"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."

Hu Firenze Camping In Town

10/10 Excellent

"I absolutely loved staying here and would stay here again! Very clean and vibrant facility. The glamping tent was such a fun place to stay. Some of the best sleep I've ever had while traveling. The staff was friendly, and the convenience of having a market and restaurant on-site was wonderful. Excellent food and service! The bus line runs right out front so it's super easy to get into the touristy section of Florence. The Ridemovi bike share bikes were nearby as well, which made transportation so easy. This place far exceeded my expectations. Highly recommended!"

Ultimo Mulino Wellness Country Hotel

10/10 Excellent

"Loved this boutique property. Stayed five nights in the newer section, Le Noci, and would love to go back. The staff were all excellent, friendly and helpful. The pool was stunning. The room was large, comfy, and quiet. Breakfast was delicious and eating on the outside terrace was wonderful as the view was incredible. The only downside was the restaurant over at the older section. Would not recommend as the waitress was rude/pushy (made the evening uncomfortable) and the food was just okay. Would recommend going to nearby Radda or Gaiole instead. Highly recommend Il Papavero in Barbischio, a few minutes east of Gaiole. The dinner we had there was the best and a highlight of the trip."

Palazzo Ravizza

10/10 Excellent

"This hotel needs another star!!! It is absolutely wonderful. The rooms are spacious, beautiful, and well supplied. The bathroom is luxurious. The staff is helpful and friendly. The breakfast is delicious and the garden is relaxing and fresh with turtles that come up and say hi while you dine. There is a library where you can take books and trade them with ones you have read. I will stay here again next time I come to Siena."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	239
Accommodation	1930 Villas
Lowest Price	CA $194
Highest Price	CA $11,354

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between CA $194 and CA $11,354 per night. Whatever your budget, you'll find something that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Gaiole in Chianti?

Gaiole in Chianti has 1930 villas to select from. Find your perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.

Why book your villa in Gaiole in Chianti with Expedia?

We think vacation time shouldn't be complicated, so if you're looking for villas at a nice price, Expedia can help. Save those pennies and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our convenient search filters to find an escape in Gaiole in Chianti that suits your needs.

How can I find cheap villas in Gaiole in Chianti?

An excellent way to locate cheap villas in Gaiole in Chianti is with Expedia's filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable rates in only a click or two.

What is there to do near my villa in Gaiole in Chianti?

There are plenty of fantastic things to do in Gaiole in Chianti. Make tracks to leading attractions like Cantalici Winery, Castle of Brolio and Meleto Castle. Badia a Coltibuono, Church of San Sigismondo and PoggioBrandani also appeal to many visitors.

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Search Gaiole in Chianti Villa Rentals from CA $194

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti villas

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa Montecastello

Luxury Villa in the Florentine hills

Villa Marcolina

Il Poggio dell'Eremita

Exclusive Estate in Florence, Private Pool, 13 bedrooms

Rooster House, cooking classes and opera

Villa Il Signorino

VILLA IL MATTO with salt pool, with spa and sauna

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

Villa Torre Among the Hills of Siena

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Italia

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia