Montignoso Rentals

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1,630 Houses

Chianti Luxury Suite, Boutique Rental, Radda in Chianti - Siena

Radda in Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfortable bed, a gorgeous bathroom and a quaint sitting area with sink and fridge. Evenings we would enjoy a glass of wine on the terrace overlooking the orchard. The gardens are filled with rows and rows of lavender. Exquisite! The entire villa is like a setting from a romantic movie about Italy. To be really decadent, we had a massage poolside that Mila arranged for us. It was heaven. It really is a place to find peace and tranquility, away from the noise of life. Mila is a charming hostess and a fountain of knowledge re the neighboring villages and history. She was fascinating to listen to and not the least bit intrusive. If we needed her she was there, otherwise she respected our privacy. My one wish would be, to have the opportunity to return again to this paradise. Thank you Mila for a wonderful experience in Chianti.

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Price per night from

$333

Restored Tuscan farmhouse with pool and views

Certaldo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

“Under theTuscan Sun” There are no words to describe the beauty here. When we drove up to the house, we thought there was a mistake. Surely this beautifully restored "Under the Tuscan Sun" farmhouse with majestic views of rolling hillside towns dotted with cypress trees, olive groves and vineyards as far as the eye could see could not possibly be the right place. But it was!! So much more than we could have imagined. Expected to see Diane Lane strolling down the road arm and arm with that crazy blonde at any time. The house inside is just as beautiful. Plenty of room...simply and tastefully decorated with everything you need for a very comfortable stay. The pictures really don't do it justice. Ann and Charly are warm and caring hosts...always quick to help our stay more enjoyable. Would absolutely recommend without hesitation!

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Price per night from

$246

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

"Blue Silence" stone house near Cinque Terre Liguria

Framura house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$467

Villa Rostolena

Vicchio villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$659

LOVELY BARN UP TO 9 WITH WIFI, AC AND PRIVATE POOL

Lucca villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

“Family Memories” Our stay was everything we expected and more. The villa was beautiful and very comfortable for our family of 8 (4 adults & 4 teenagers). There was plenty of room for everyone, including 3 different tables where we could all dine together. We cooked most nights and had everything we needed. We loved having a full-size refrigerator and a washing machine. The location was very convenient to grocery shopping and the train station for our day trips. The scenery was incredible and we enjoyed relaxing by the pool. Our hosts were very attentive and helpful. They gave us very helpful information on the area and arranged a wonderful chef for an evening. It is obvious the Della Santa family takes great pride in their property and wants to make sure their guests are happy and have everything they need. We highly recommend this property for a memorable vacation.

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Price per night from

$613

Converted Barn Vacation Rental in Tuscany

Certaldo cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“We had a very relaxing stay in a beautiful setting.” The house is newly renovated and very clean. The setting is spectacular with beautiful views. It is in a great location for easy access to popular tourist attractions. However, we did have to provide some household essentials such as dish soap, sugar, and a few other kitchen basics that we couldn't take back with us, as we were traveling overseas.

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Price per night from

$234

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

Match: Private pool

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Price per night from

$614

Village Gebbia

Civitella in Val di Chiana house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$250

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$983

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Price per night from

$111

“Great” we had a great time the house and owner are great people and we loved the location xx

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Price per night from

$271

Casale Scope

Molazzana house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$505

Smooth hills

Montelupo Fiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$282

Stunning Country Villa at Montefili in Greve, Chianti

Greve in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$739

Villa Cerbaie

Castelfranco di Sotto villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$562

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$123

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

Match: Private pool

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Price per night from

$115

Villa Donatella

Borgo San Lorenzo villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Private pool

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Price per night from

$1,075

Villa Il Castagno

Monsummano Terme villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 19

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Price per night from

$721

Big garden,own pool and wheelchairfriendly, pets

Oliveto house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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Price per night from

$479

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$766

La Foresteria del Castello della Paneretta

Barberino Val d'Elsa apartment

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$983

2 Farmhouses with 5 bedrooms and Pool in Countryside near Lucca

Valdottavo house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Lovely home and amazing view!” Friendly welcome, home with everything you need so you feel immediately at home. Even better than the pictures on the website. When you return from your trip to Lucca, Pisa or Florence you can relax in the comfortable swimmingpool with amazing view on the valley.

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Price per night from

$295

San Romolo

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$210

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

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Price per night from

$553

Villa Le Terrazze in Florence, views, pool, no car needed

Florence villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“It was the perfect place for us. Clean, roomy, easy to get to F” The Villa is beautiful! Lorenzo was a great host and he helped arrange transportation from the airport. We had taken a late train from Rome and got to the villa felt in the evening feeling very tired. Lorenzo was great the villa was awesome and we felt at home immediately. There were eight of us and there was plenty of room to spread out. Pros Beautiful Villa Very Clean Incredible View Wonderful Gardens Plenty of Room Full Kitchen with utensils Easy to Get to Florence (bus stop within walking distance) Cafe and small market within walking distance Lorenzo was great Cons Cannot think of any The location of the villa was perfect for our group. It is out of the hustle and bustle of the city but close enough to get into the city quickly. It only takes about 15 minutes to get to Florence by bus (which was easy to use, clean, and never too crowded.) By our bus stop there are a small market and cafe. So we could get espresso while waiting for our bus. One night we decided to eat in and the kitchen was equipped with all the utensils to make a full dinner. The Villa just added to the magic we were having on our trip and we would highly recommend it.

Match: Private pool

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Price per night from

$1,449

Alice 1

Castiglioncello apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private pool

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Price per night from

$248

Luxury Villa at Greve in Chianti

Greve in Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$614

holiday house

Carmignano villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$677

5 bedroom villa with pool in Tuscany

Impruneta house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 40 minutes

Match: Private pool

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Price per night from

$1,214

Uliveta of Luschi

Castiglioncello house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$338

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Price per night from

$676

Villa la Mandragola

San Casciano in Val di Pesa villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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$1,228

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Price per night from

$413

223 - Family Villa with Pool and Tennis Court

Terranuova Bracciolini villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$289

Country House Nazzano in Chianti area near S.Gimignano (from 4 to 10 people)

Gambassi Terme villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location” We spent a wonderful week in this property which was located centrally in the Tuscany Region. Two families were easily accommodated and we were able to link the connecting rooms as if we were in one large family home. Miriam and her husband were helpful, kind and gracious hosts and nothing was ever too much trouble. All the comforts of home and the peace and quiet of an idyllic getaway. We will return to the incredible property...if our friends and family don't beat us to it!

Match: Private pool

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Price per night from

$369

Casale Tignano

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$388

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