Showing

$76

Book

Private Hayloft with Garden near Montespertoli

Montespertoli house
2 BR / 1 BA / Sleeps 6 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Farmhouse, 2 Bedrooms + Convertible bed(s), 1 Bath (Sleeps 3-6) You’ll find us in the heart of Tuscany, in the area known as the “Chianti towns”. We're located in Montespertoli, a typical Tuscan town easily reached from all over the region. This is a land of gentle hills dotted with vineyards that denote …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(4)

piccolo paradiso

Left on Apr 17, 2012 for a stay in March 2012

sono stata con la mia famiglia a fine marzo per un piccolo soggiorno in questo angolo di paradiso...il clima, il paesaggio, l' imtimita', la pace...tutti elementi che avvolgono questo incantevole posto, in cui spero di poter tornare...

$43

Book

Casa Vacanze Il Tramonto Sul Chianti: Apt. Bacco

Montespertoli condo
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

You’ll find us in the heart of Tuscany, in the area known as the “Chianti towns”. We're located in Montespertoli, a typical Tuscan town easily reached from all over the region. This is a land of gentle hills dotted with vineyards that denote authentic Tuscan scenery. It is a fertile land, whose soil produces …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Bellissimo...

Left on Mar 23, 2014 for a stay in March 2014

Sono stata qui a passare un week-end con mio marito, lontano dalla confusione della città.
Nonostante non fosse ancora primavera siamo rimasti colpiti dal paesaggio e dal giardino completamente ricoperto di margherite in fiore.
Siamo rimasti colpiti dalla disponibilità del proprietario che ci a aiutato ad organizzare una gita tra le cantine della zona ed a scoprire un ristorantino veramente …

Villa Virginia - Montespertoli vacation rentals
1 / 16

$472

Inquire

Villa Virginia

Montespertoli villa
6 BR / 5 BA / Sleeps 12 | Quick view

Details

A fine and elegant villa rental situated in Montespertoli in a scenic position surrounded by olive groves and large vineyards from which one of the best Tuscany wines is produced, the famous “Chianti Classico”. Perfect for those wanting to relax in the Chianti countryside, this property is also the best starting …
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
1219 - Montespertoli vacation rentals
1 / 62

$1,843

Inquire

1219

Montespertoli castle
6 BR / 6 BA / Sleeps 12 | Quick view

Details

Castello di Renai is a wonderful historical castle in Tuscany for rent. This graceful country residence is near the ancient town of Castelfiorentino on the Francigen Route. This Tuscan castle for rent dates back to the early years of the 13th century. External description: Located in the Tuscan countryside, Castello …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for the elderly - ask

$784

Inquire

Villa Teatro Vacation Rental with Pool

Montespertoli house
6 BR / 7 BA / Sleeps 12 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Villa Teatro is an extraordinarily tastefully and impeccably designed country house. Strategically positioned in the center of the “Golden Triangle” between Florence, Siena and Pisa the property sits on top of a hill, surrounded by olive groves. The large stone farmhouse was built at the beginning of the 1800s. …
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Garden
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

perfect

Left on Jun 21, 2010 for a stay in June 2010

Perfect for business, perfect location. Really a Dream

Villa Montegufoni between Florence and Sienna - Montespertoli vacation rentals
1 / 21

$440

Book

Villa Montegufoni between Florence and Sienna

Montespertoli villa
8 BR / 6 BA / Sleeps 16 | Quick view

Details

Accommodations: Villa, 8 Bedrooms, 6 Baths (Sleeps 8-16) ' The villa with sleeps 16 stands in a panoramic position atop a hill overlooking onto the vineyards in the Florentine countryside, near the village of Montespertoli. The structure has been recently renovated (winter 2008-2009) and is composed of two twin …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask
1 / 38

$643

Inquire

CASA EGLE

Montespertoli villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Casa Egle is an elegant Tuscan farmhouse set in a beautiful garden.  This villa features a nice pool and stunning views over the rolling hills of this wonderful region.  Olive groves, vineyards, woods and country estates are all in view.  Its location is between Florence and Siena, with the towns of Certaldo, …
  • Wireless Internet
  • Washing Machine
  • A/C or climate control
  • Fitness Room
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 28

$686

Inquire

Casa Monticello

Montespertoli house
4 BR / 5 BA / Sleeps 8 | Quick view

Details

Casa Monticello is an elegant Tuscan farmhouse with glorious views over the rolling hills of Chianti. Art lovers will be exposed to an illimited choice of interesting excurtions. The location is ideal - between Florence and Siena and close to Certaldo, Montespertoli and San Gimignano, in the very heart of Chianti. One…
  • Shared outdoor pool (unheated)
  • Balcony or terrace
  • Garden
  • Grill
  • Safe
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 50

$730

Inquire

VILLA MIMA

Montespertoli villa
6 BR / 6 BA / Sleeps 14 | Quick view

Details

Villa Mima is a splendid 18th century stone farmhouse that lies roughly equal distance between Florence, Siena, Pisa and the seaside. Gatherings of friends and family love this villa for its ideal location and dominant position with expansive views over the beautiful Chianti hills. Villa Mima rents from SATURDAY to …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 19

$220

Book

Villa Montegufoni (Barn 1)

Montespertoli villa
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Indipendent Villa on top of a hill in the Chianti with panoramic view on the vineyards Montegufoni Villa with 8 beds is situated atop a hill, with panoramic view over the vineyards of the Chianti countryside, near the small town Montespertoli location 'Montegufoni. Quiet and peaceful a place is really relaxing…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

$189

Book

Nice indipendent house among Florence Siena Lucca

Montespertoli house
3 BR / 1 BA / Sleeps 5 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

La Cipressaia is an independent house of 85 m2 with 4 rooms on 2 floors furnished in a comfortable and tasteful way. Dining room / living room with satellite TV, safe, sofa, armchairs, table and chairs. Kitchenette with 4 points fire, microwave, fridge / freezer. 1 large double bedroom, 1 single bedroom and a double …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Outdoor Dining Area
  • Patio
  • Parking
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great choice

Left on Jun 02, 2012 for a stay in May 2012

We come to Il Poggetto every year around may. We just were there last week for the 5th time! And it is always a joy to come back and spend a wonderful time with the family in this kind of paradise. The surrounding is more than just beautiful, the location near cities like Florence and Pisa and lots of small lovely villages, makes it easy to have different day trips every time. And the best part …

$118

Book

3-room apartment in the heart of Tuscany

Montespertoli condo
2 BR / 1 BA / Sleeps 4 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

La Pergola is a 3-room apartment on the ground floor furnished with care and warmly. Living / Kitchen: Living room with sofa and armchairs, free WiFi, satellite TV, safe, table and chairs. Kitchen with 4 hotplates, microwave, fridge / freezer and utensils. 1 double bedroom with fan and 1 room with 2 single beds that…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Outdoor Dining Area
  • Patio
  • Parking
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Very quiet, private surrounding

Left on Aug 11, 2013 for a stay in July 2013

Although very hot, it was one of the best experiences for us. No worries and easy to travel to Firenze.

1 / 47

$1,365

Book

Villa del Vallone

Montespertoli condo
6 BR / 1 BA / Sleeps 12 | Quick view

Details

The most unforgettable Villa experience that you could ever have. Not only for the sheer luxury, the comforts of modern amenities, combined with the grand style of this magnificent establishment, but also for the location, tranquility and a breathtaking surrounding outdoor Tuscan landscape. We can confidently state…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 20

$549

Book

Villa I Leoni Between Florence Sienna and Pisa - 1 km to village - Aircond.

Montespertoli villa
10 BR / 8 BA / Sleeps 21 | Quick view

Details

Surrounded by olive groves and vineyards, the villa (21 sleeps) stands in panoramic position atop a hill offering a magnificent view of the Tuscan countryside stretching as far as the eye can see. It lies at the centre of the triangle Florence, Pisa and Sienna, Central place in Tuscany to visit almost all its major …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible
1 / 12

$141

Book

Restored hay barn in Chianti with swimming pool

Montespertoli farmhouse barn
1 BR / 1 BA / Sleeps 4 | Quick view

Details

La Loggia is a 3-room apartment furnished with great care and antique furniture. ? Living / Dining room: Large living room with sofa bed, satellite TV, safe, fan, table and chairs. ?Kitchen with 4 points fire, oven, fridge / freezer and utensils. ? 1 large double bedroom with fan. Bathroom with shower. ?Separate …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Outdoor Dining Area
  • Patio
  • Parking
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

$283

Inquire

Tuscany Farmhouse Close to a Castle - Casa Berto

Montespertoli house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

If you have ever had a hankering to stay in a historic Castle in Tuscany amidst vineyards and Chianti towns, this fits the bill. Owned by a Florentine family, this castle estate is well located for day trips throughout the region. There is a restaurant onsite open six days a week and a lovely garden and pool area. The…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Central heating
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Lyssa's review of Casa Berto

Left on Aug 31, 2006 for a stay in August 2006

We had a great time! We rented several units in the castle and this house to accommodate our family group of about 20. It was just perfect. It was exactly what we wanted and expected.

It was awesome beautiful. Location was great.

For the older people in our group, the walk into town was too far and too steep to be comfortable.

$220

Book

Casale Il Poggiarello

Montespertoli house
6 BR / 3 BA / Sleeps 13 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

CASALE IL POGGIARELLO - Country Holiday House Enclosed in a 5000 sqm area in the heart of the Chianti, it is an oasis where you can enjoy an absolute relax and privacy. Situated in a predominant position on the Virginio Valley, our property will be for your own private use, offering you total independence. You will …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Very old house in an excellent location and nice area.

Left on May 09, 2014 for a stay in April 2014

The house is an old house sitting in an excellent location. The house is beutiful and view is amqzing. It has its large back yard you can stay at, just looking at the winery and the fields around.

Tye house has a fine kitchen with large refrigirator and equiped to cook your meals.

The place is not very spoiling, some equipment is just very old (tv, closets, blankets). We could enjoy a big …

$551

Inquire

Large Tuscany Villa in the Chianti Region - Villa San Paolo

Montespertoli house
5 BR / 4 BA / Sleeps 10 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

With its location in the hills of the Chianti wine zone, this Tuscany villa is a great destination for the wine lover! Just three kilometers away from this Tuscany vacation rental is the renowned Wine Culture Center in Montespertoli, along with plenty of opportunities to go wine tasting. This lovely and classy villa …
  • Internet Access
  • Washing Machine
  • Central heating
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Phyllis's review of Villa San Paolo

Left on Jul 31, 2008 for a stay in July 2008

It was a wonderful experience. We had rental cars and took a day trip each day all about 1 hour villa-to-location. Did not get lost due to GPS systems in the cars and were able to enjoy the magnificent countryside.

I thought the outside area was beautifully maintained, comfortable and relaxing. The pool area was a treat after returning late afternoons from various surrounding towns. The grounds …

$299

Inquire

Tuscany Apartment with Pool near Restaurant - Poggio Sant Andrea

Montespertoli house
7 BR / 6 BA / Sleeps 18 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Located in the hills of Chianti within a hamlet of houses, these apartments in Tuscany are just right for a large family or group of friends. This villa rental with a pool is ideal for those looking for a quiet vacation in Tuscany with a picturesque setting. A trattoria and restaurant are within walking distance while…
  • Shared outdoor pool (unheated)
  • Washing Machine
  • Grill
  • Dishwasher
  • Stove or Oven
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Donna's review of Poggio Sant'Andrea

Left on Jun 30, 2009 for a stay in June 2009

Very clean and well presented properties, the outside areas were lovely too.

The pool area and outside BBQ area

Nothin

Found the property very remote.

1 / 19

$60

Book

BRIGITTE'S COTTAGE

Montespertoli condo
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Apartment located in a former country house recently renovated, with a total of 15 units. Located close to Empoli and Florence, you can easily reach important places of interest such as Florence, Certaldo, San Gimignano, Siena, Pisa and the Tuscan coast. The apartment is located on the ground floor, with private …
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 16

$55

Book

Villa bifamiliare con giardino, Chianti Fiorentino

Montespertoli villa
4 BR / 2 BA / Sleeps 10 | Quick view

Details

The new building, has two cozy, bright apartments with independent entrance and garden. The entire property is enclosed and delimited by a single access. To the holidayers' disposition, barbecue and swimming pool CASAMARTA is the first floor apartment, about 70 sqm. E 'consists of a large living / dining room, 3 …
  • Internet Access
  • Fireplace
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Smoking allowed - ask
  • Suitable for the elderly - ask
1 / 37

$212

Inquire

Paolo

Montespertoli house
5 BR / 3 BA / Sleeps 12 | Quick view

Details

This private villa with pool near Florence is perfect for 10 people with 5 bedrooms, barbecue and many other amenities. Additional amenities include: heating.
  • Garden
  • Dishwasher
  • Refrigerator
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 27

$1,178

Inquire

Chianti

Montespertoli house
6 BR / 6 BA / Sleeps 14 | Quick view

Details

Villa Chianti is a wonderful villa for rent in the famouse chianti region in northern Tuscany close to florence, this Tuscan Villa can host up to 12+2 people, swimmingpool. Additional amenities include: pets considered, heating.
  • Garden
  • Dishwasher
  • Refrigerator
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 39

$138

Book

Cottage finely renovated with swimming pool overlooking the Tuscan hills

Montespertoli cottage
2 BR / 1 BA / Sleeps 4 | Quick view

Details

This beautiful country property is immersed in the verdant hills around Florence, an ideal retreat for country lovers seeking beautiful countryside and tranquillity. We let the beautifully converted and restored barn near the house of about 100 square metres. The cottage is located on the same property as the main …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
1 / 42

$4,047

Inquire

Castle Rental in Tuscany, Montespertoli (Chianti Area) - Il Castello

Montespertoli house
43 BR / 35 BA / Sleeps 120 | Quick view

Details

If you have ever had a hankering to stay in a historic Castle in Tuscany amidst vineyards and Chianti towns, this fits the bill. Owned by a Florentine family, this castle estate is well located for day trips throughout the region. There is a restaurant onsite open six days a week and a lovely garden and pool area. The…
  • Washing Machine
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

$438

Inquire

CastleApartment Rental in Tuscany, Montespertoli (Chianti Area) - Il Castello Freschi

Montespertoli condo
4 BR / 3 BA / Sleeps 9 | Quick view
Average1 Reviews

Details

Reviews

(1)

If you have ever had a hankering to stay in a historic Castle in Tuscany amidst vineyards and Chianti towns, this fits the bill. Owned by a Florentine family, this castle estate is well located for day trips throughout the region. There is a restaurant onsite open six days a week and a lovely garden and pool area. The…
  • Shared outdoor pool (unheated)
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Amy's review of Il Castello - I Freschi

Left on Sep 30, 2006 for a stay in September 2006

We had a very pleasant stay and would recommend the property.

The location and the castle itself.

Two things: (1) Our bedroom window did not have a screen. We requested one the second day we were there and the staff told us a repair man would be coming the next day. However, we never received a screen. As a result, our sleeping conditions were uncomfortable and our baby received over 15 …


Looking for more rentals?


We're showing only results that match your dates and preferences.


See all 100 Montespertoli rentals, all 0 Tuscany rentals, or start a new search.


There are no more results in Montespertoli. Top of page