Tuscany Rentals with Pools

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4,171 villas in Tuscany with pools

MAGNOLIA house in a historical monumental estate.

San Pietro a Marcigliano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$199

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$231

CASANOVA APARTMENT

Pistoia b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$100

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 4 minutes

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Price per night from

$112

Villa Rostolena

Vicchio villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$666

Fattoria di Arsicci, holiday house weekly rented.

Badia Tedalda villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 15

“A dream of a house for a large family gathering!” For our Silver Wedding celebration we gathered here with 15 family members aged from 5 to 78years old and had a wonderful time - even the teenagers! There was plenty of space in the house and around it with a pool and wonderful park. Granny sat every morning in the rose garden. There were plenty of possible games to play, LPs of Italian Opera to listen to, walks to take and excursions to make. The beds and bathrooms were wonderful and the kitchen well equipped. We would love to go back some time.

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Price per night from

$274

Gorgeous independent house, in Chianti, with pool

San Casciano in Val di Pesa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$261

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Price per night from

$640

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$174

Village Gebbia

Civitella in Val di Chiana house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$253

Contryhouse 9 kms to Florence with pool 4+2

Strada in Chianti farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$187

Farmhouse in the Chianti Classico area, App. 2+1g

Strada in Chianti farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$125

“Nice place, amazing view -, scary drive!” Large rooms, nice old farmhouse that's been recently renovated. Owners very friendly. Amazing restaurant just a couple of miles down the road. Amazing views, but there's a reason - the last 400m (ish) drive up to the property is steep - serious hairpin bends on narrow road.

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Price per night from

$187

The Poacher

San Polo in Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 29 minutes

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Price per night from

$236

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

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Price per night from

$187

Casale Scope

Molazzana house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$510

Smooth hills

Montelupo Fiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$285

Maremma 2

Marsiliana apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$133

Organic farm tucked away in the Tuscan hills-apt. Maria

Montaione house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$177

Words Villa D'oro

Guamo villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$449

Villa Cerbaie

Castelfranco di Sotto villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$568

Podere Vignola farmhouse near Florence - Loggia

Florence house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$435

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Price per night from

$187

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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Price per night from

$234

Alice 2

Castiglioncello apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$255

Restored Farmhouse w/Pool among Chianti vineyards

San Casciano in Val di Pesa house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$547

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Price per night from

$187

Villa Donatella

Borgo San Lorenzo villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

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Price per night from

$1,087

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$190

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$210

Villa Il Castagno

Monsummano Terme villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 19

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Price per night from

$728

La Volpe sleeps 4 + 1 ( on request )

San Polo in Chianti villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 29 minutes

Match: Swimming pool

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Price per night from

$249

Colline House, in Tuscany, Residence Il Palazzo

Pergine Valdarno house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$74

Siena House, Residence in Tuscany, Farm Holiday

Pergine Valdarno apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Swimming pool

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Price per night from

$112

Piettorri Rosemary

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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Price per night from

$154

Guidi

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$118

San Romolo

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$213

Villa Maura in Tuscany: pool, private garden & BBQ

Fucecchio villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic holiday at Villa Maura” This is our second visit to La Scuola in Tuscany and our group consisted of four adults. It has an ideal location for sight seeing, being close to Pisa, Florence, and Lucca, not to mention the vineyards and wine tasting, but you do need a vehicle as it is special in its remoteness from urban life. It is in a beautiful setting, within the rolling hills and picturesque scenery you expect from the area. There is a swimming pool to be shared by the few apartments but it is mainly very quiet for a relaxing day with a good book. We have stayed in both an apartment and the Villa Maura which is an exceptional property with all the facilities a family could need. Both met our needs more than adequately. Tiziana the proprietor gives exceptional customer service and this year she helped us with a series of visits with local dignitaries and local places in the area in our efforts to establish some things of unexpected but special historical interest to my family. She has, on both our visits, offered her time and service to help us out. Tizzie even arranged our first basket of shopping to ensure we had groceries for our arrival as it was late in the day and at the weekend. We enjoy a balance between touring and relaxing and this gives the opportunity to do both. If you don't wish to drive into cities there is adequate railway provision locally to get where ever you wish to go. The town of Fuccechio has an open air market each week and there are large local supermarkets close at hand. There are detailed information packs in the Villa and apartments to help you. I would highly recommend this property as a base to chill out or as a base to see the wonders of historical Tuscany or as for us, a chance to do both.

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Price per night from

$373

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