Make a holiday rental home or villa in Gaiole in Chianti, Italy your home away from home

Gaiole in Chianti is a municipality in the Province of Siena, in the beautiful Italian region of Tuscany. Located just 40kms southeast of Florence and 15kms from Siena, Gaiole in Chianti is easily accessible, and has remained a popular choice with tourists for the last few decades.

The Chianti region is regarded as the ‘Heart of Tuscany’, and is identified by its thousand year-old history of winemaking, and strong gastonomical culture. More than half the area is woodland, making it ideal for a range of outdoor activities.

There is a wide range of accommodation available in Gaiole in Chianti, including luxury villas and rural farmhouses, making a self-catering holiday the best choice of vacation.

Things to do in Gaiole in Chianti, Italy

The Chianti region is one of the most famous wine producing regions in the world, meaning wine tasting forms a huge part of any holiday here. Many wineries offer tasting sessions, and you can turn up by yourself or join an organized tour. Some wineries offer food, and the best thing to do is take your time, and slow your pace to that of the locals.

Gaiole in Chianti has many sites which date back to the 11th and 12th Centuries, including the Castle of Broilo, the Abbey of Coltibuono, and the Pieve of San Marcellino. The Romanesque parish church of Santa Maria e Spaltenna dates back to the 12th Century, and you can enjoy a high-class meal in the surroundings of the old cloister. The picturesque old town warrants a good deal of exploring.

It is also recommended that you get out into the beautiful surrounding countryside, hike in the hills and take in the scenery. The great weather, spectacular scenery and high quality of living have made Gaiole in Chianti ‘Europe’s Most Idyllic Place to Live’, as voted by an expert panel on forbes.com.

Places to visit on holiday in Gaiole in Chianti, Italy

Gaiole in Chianti is part of the Chianti Storico, a historical area which is also home to the other Chianti Classico towns of Castelinna in Chianti and Radda in Chianti, both of which warrant a day visit.

Due to its close proximity to the famous Italian cities of Florence and Siena, it is possible to pay a visit to these cities whilst staying in the Chianti region, but still return to your holiday rental accommodation in the evenings, giving you the best of both worlds.

Weather in Gaiole in Chianti, Italy

Gaiole in Chianti experiences hot summers, which regularly reach over 35C. Due to the fact that you are likely to be spending a lot of time outdoor during your stay here, it may be more comfortable to visit in the spring or autumn, as the temperatures are cooler and more pleasant for outdoor activities.

Flights to Gaiole in Chianti, Italy

Florence Airport (FLR) is just 40km away, but there is a lack of direct flights from UK airports. A cheaper and more viable option is Pisa Airport (PSA), which is around two hour’s drive from the Chianti region, and receives an abundance of flights from budget airlines.

Self-catering holiday homes in Gaiole in Chianti

Refine Your Search Start a New Search
Find by availability dates:
and/or by weekly rental rate
(in £ GBP):
Current Criteria:
(remove all criteria)

Compare Selected
compare

BEL SORRISO: DREAM LOCATION IN CHIANTI - SPACIOUS HOME, POOL & GARDEN

— Property 76939
Gaiole in Chianti apartment rental - Toward sunset
2 Bedrooms, Sleeps 4,
Apartment, 2 Bathrooms, rural, village, pool
Rates - per property (GBP)
£766 - £946/week
Calendar Updated 10 Nov 2009

Property Review

'The isolation of this gem amidst the stunning Tuscan scenery has made this a most relaxing and peaceful holiday. Essential visits to some of Italy's most historic centres of architecture and...
compare

Luxury villa, garden whit private pool, all comfort, relax Bike,

— Property 432154
Gaiole in Chianti villa rental - Villa
5 Bedrooms, Sleeps 1,
Villa, 3 Bathrooms, rural, pool
Rates - per property (GBP)
£270 - £450/night
£541 - £1,261/week
compare

Stunning location, pool and one apartment in lovingly restored house

— Property 17455
Gaiole in Chianti apartment rental - Nestling in the hills, surrounded by great views
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, rural, garden
Rates - per property (GBP)
£613 - £946/week
Calendar Updated 10 Nov 2009

Property Review

We spent our first week in this lovely peaceful part of Tuscany, well off the beaten track in the most delightful setting. The spacious apartment is tastefully and artistically presented which...
compare

Beautiful Villa in Chianti, great views, A/C,luxury pool, Gaiole in Chianti area

— Property 69515
Gaiole in Chianti villa rental - Luxury Villa in Chianti fantastic infinity pool
12 Bedrooms, Sleeps 22,
Villa, 9 Bathrooms, rural, village, pool
Rates - per property (GBP)
£3,829 - £7,018/week
Calendar Updated 8 Nov 2009

Property Review

Sabrina, Staying at the beautiful Villa Tere in northern Tuscany gives visitors easy day trips to Siena, Florence (1-hour train), Arezzo, San Gimignano, and the 'Chianti' towns. housekeepers show...
compare

Tuscany, Chianti, luxury Villa, Pool, Park

— Property 405660
Gaiole in Chianti villa rental - Entrance
5 Bedrooms, Sleeps 11,
Villa, 5 Bathrooms, mountain, rural, pool
Rates - per property (GBP)
£631 - £1,081/night
£2,964 - £3,505/week
Calendar Updated 7 Nov 2009

Property Review

Peace, tranquility...all the beds are kingsize...the pool is just the right temperature - even in August. The owners, who live at the end of the drive, are consumate hosts - get them to cook for...
compare

Vacation Rentals on Wine Estate in Chianti, Tuscany, Italy

— Property 149269
Gaiole in Chianti property rental - The Residence at Le Miccine
3 Bedrooms, Sleeps 6,
2 Bathrooms, rural, garden
Rates - per property (GBP)
£1,037 - £1,677/week
Calendar Updated 31 Oct 2009

Property Review

Promises were made prior to our arrival so we naturally arrived with anxiety and with rather high expectations for first-time renters. All promises were kept and exceeded beyond our wildest...
compare

Delightfully restored Chianti farmhouse

— Property 416200
Gaiole in Chianti villa rental - The swimming pool above the house
5 Bedrooms, Sleeps 12,
Villa, 4 Bathrooms, mountain, rural, daily maid service
Rates - per property (GBP)
£1,892/week
compare

Restored Chianti farmhouse, large pool, hilltop, 30 private acres - Farmhouse and studio

— Property 76109
Gaiole in Chianti villa rental - Eastern aspect of main house
6 Bedrooms, Sleeps 12,
Villa, 5 Bathrooms, mountain, rural, pool
Rates - per property (GBP)
£550/night
£2,100 - £2,600/week
compare

Restored Chianti farmhouse, large pool, hilltop, 30 private acres - Studio

— Property 76109
Gaiole in Chianti house rental - Eastern aspect of main house
Studio, Sleeps 2,
House, 1 Bathroom, mountain, rural, pool
Rates - per property (GBP)
£200/night
£600 - £750/week
compare

Casa Kiwi is nestled in the Chianti hills in a peaceful location with great view

— Property 436119
Gaiole in Chianti villa rental - Casa Kiwi
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, rural, garden
Rates - per property (GBP)
£1,183 - £2,072/week
compare

Chianti Villas surrounded by olive groves and Vineyards with pool - Eolo

— Property 81793
Gaiole in Chianti villa rental - View from Eolo
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, rural, village, pool
Rates - per property (GBP)
£631 - £1,081/week
Calendar Updated 13 Oct 2009

Property Review

Absolutely excellent! The standard of build, the facilities and the location were lovely. The design layout of the units ensured total privacy so that we were never aware or disturbed by our...
compare

Chianti Villas surrounded by olive groves and Vineyards with pool - Il Sole

— Property 81793
Gaiole in Chianti villa rental - Montefiorile pool
2 Bedrooms, Sleeps 4,
Villa, 2 Bathrooms, rural, village, pool
Rates - per property (GBP)
£495 - £901/week
Calendar Updated 13 Oct 2009

Property Review

Absolutely excellent! The standard of build, the facilities and the location were lovely. The design layout of the units ensured total privacy so that we were never aware or disturbed by our...
compare

Chianti Villas surrounded by olive groves and Vineyards with pool - Taglialegna

— Property 81793
Gaiole in Chianti villa rental - Vinaio View
1 Bedroom, Sleeps 4,
Villa, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£360 - £622/week
Calendar Updated 13 Oct 2009

Property Review

Absolutely excellent! The standard of build, the facilities and the location were lovely. The design layout of the units ensured total privacy so that we were never aware or disturbed by our...
compare

Chianti Villas surrounded by olive groves and Vineyards with pool - Scorpione

— Property 81793
Gaiole in Chianti villa rental - Scorpione View
1 Bedroom, Sleeps 3,
Villa, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£360 - £676/week
Calendar Updated 13 Oct 2009

Property Review

Absolutely excellent! The standard of build, the facilities and the location were lovely. The design layout of the units ensured total privacy so that we were never aware or disturbed by our...
compare

Chianti Villas surrounded by olive groves and Vineyards with pool - Bacco

— Property 81793
Gaiole in Chianti villa rental - View from Eolo
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, rural, village, pool
Rates - per property (GBP)
£541 - £968/week
Calendar Updated 13 Oct 2009

Property Review

Absolutely excellent! The standard of build, the facilities and the location were lovely. The design layout of the units ensured total privacy so that we were never aware or disturbed by our...
compare

Magnificent villa in the heart of the Chianti region, Tuscany - Panorama

— Property 79371
Gaiole in Chianti apartment rental - swimming pool
1 Bedroom, Sleeps 3,
Apartment, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£356 - £495/week
compare

Magnificent villa in the heart of the Chianti region, Tuscany - La Contessina

— Property 79371
Gaiole in Chianti villa rental - La Contessina
1 Bedroom, Sleeps 4,
Villa, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£360 - £716/week
compare

Magnificent villa in the heart of the Chianti region, Tuscany - La Scala

— Property 79371
Gaiole in Chianti villa rental - La Scala
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, rural, village, pool
Rates - per property (GBP)
£721 - £1,257/week
compare

Magnificent villa in the heart of the Chianti region, Tuscany - La Vigna

— Property 79371
Gaiole in Chianti villa rental - La Vigna garden
2 Bedrooms, Sleeps 4,
Villa, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£450 - £1,036/week
Calendar Updated 13 Oct 2009

Property Review

Client - Barb Simasko Nationality - US We loved Montebuoni and the area. Everything about our two weeks was perfect and our time there was the best part of our month long trip. THANK YOU,...
compare

Magnificent villa in the heart of the Chianti region, Tuscany - L'Oliveta

— Property 79371
Gaiole in Chianti villa rental - L'Oliveta Villa in Tuscany
2 Bedrooms, Sleeps 4,
Villa, 1 Bathroom, rural, village, pool
Rates - per property (GBP)
£450 - £1,126/week
Calendar Updated 13 Oct 2009

Property Review

Client - Barb Simasko Nationality - US We loved Montebuoni and the area. Everything about our two weeks was perfect and our time there was the best part of our month long trip. THANK YOU,...
compare

Podere Lucignano Secondo - Charming Villa in Chianti - Tuscany - “Le Logge”

— Property 64960
Gaiole in Chianti villa rental - The property
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, rural, garden
Rates - per property (GBP)
£173 - £225/night
£1,216 - £1,577/week
Calendar Updated 15 Sep 2009

Property Review

In a trip filled with great sights and experiences, the one thing my family & I keep coming back to as THE highlight was this superb property. Although it's a bit out of the way (@ 15k from...
compare

Podere Lucignano Secondo - Charming Villa in Chianti - Tuscany - “La Mangiatoia”

— Property 64960
Gaiole in Chianti villa rental - Terrace
2 Bedrooms, Sleeps 4,
Villa, 1 Bathroom, rural, garden
Rates - per property (GBP)
£154 - £193/night
£1,081 - £1,351/week
Calendar Updated 11 Sep 2009

Property Review

Absolutely stunning in every regard. From the personal warm welcome, to the final farewell, we couldn't have asked for more. Comfortable, clean, secluded and well equipped. We were able to...
compare

Old restored mill in indipendent position, large garden, pool, small lake

— Property 506227
Gaiole in Chianti mill rental - main building with court and fontaine
5 Bedrooms, Sleeps 14,
Mill, 4 Bathrooms, rural, pool
Rates - per property (GBP)
£1,622 - £2,883/week
compare

Restored Chianti farmhouse, large pool, hilltop, 30 private acres - Farmhouse

— Property 76109
Gaiole in Chianti villa rental - Eastern aspect of main house
5 Bedrooms, Sleeps 11,
Villa, 4 Bathrooms, mountain, rural, pool
Rates - per property (GBP)
£400/night
£1,800 - £2,300/week
Calendar Updated 4 Aug 2009

Property Review

This is a very nice house indeed with amazing views. The location is so quiet and peaceful with not another house or building in sight. It has the best equipped kitchen we have experienced in...
compare

Chianti typical Casa Colonica with pool - Fico

— Property 88264
Gaiole in Chianti barn rental
1 Bedroom, Sleeps 6,
Barn, 1 Bathroom, rural, village, garden
compare

Chianti typical Casa Colonica with pool - Cipresso

— Property 88264
Gaiole in Chianti farmhouse rental
4 Bedrooms, Sleeps 9,
Farmhouse, 3 Bathrooms, 1 Separate Toilet, rural, village, pool
Rates - per property (GBP)
£1,712/week
compare

Easyreserve - Adine

— Property 69090h
2 Bedrooms/2 Bathrooms House (Sleeps 5 tv, starting at £471/week
compare

Easyreserve - Villa Vistarenni - Villa

— Property 62539h
4 Bedrooms/4 Bathrooms House (Sleeps 7 dish washer, fireplace, grill, telephone, tennis, tv, dialup access, private pool, starting at £495/night £2,304/week
compare

Easyreserve - Villa Vistarenni - Togna Cottage

— Property 62544h
2 Bedrooms/1 Bathroom House (Sleeps 4 fireplace, grill, telephone, tennis, tv, dialup access, private pool, starting at £149/night £790/week
compare

Easyreserve - Villa Vistarenni - Chiara Cottage

— Property 62543h
3 Bedrooms/1 Bathroom House (Sleeps 6 dish washer, fireplace, grill, telephone, tennis, tv, dialup access, private pool, starting at £178/night £813/week