South Florence Rentals with Pools

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566 Houses in South Florence with pools

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

$332

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

$258

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: Swimming pool

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Price per night from

$615

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

$185

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

$123

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

$984

Organic Wine & Olive Estate - Apartment Rose

Greve in Chianti cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$271

The Poacher

San Polo in Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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Price per night from

$271

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.

Match: Swimming pool

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Price per night from

$185

Sangiovese country house with pool in Chianti area

Tavarnelle Val di Pesa apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$185

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

$740

Podere Vignola farmhouse near Florence - Loggia

Florence house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$431

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

$541

La Volpe sleeps 4 + 1 ( on request )

San Polo in Chianti villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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Price per night from

$246

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$770

La Foresteria del Castello della Paneretta

Barberino Val d'Elsa apartment

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$984

San Romolo

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$211

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

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Price per night from

$555

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: Swimming pool

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Price per night from

$1,451

Luxury Villa at Greve in Chianti

Greve in Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$617

Villa il Castellaccio in Greve in Chianti Flat #3

Greve in Chianti house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“A lovely place!” We had a really lovely holiday. The location is excellent, being in the heart of Chianti, a peaceful place sorrounded by vineyards and olive grooves, but not far from the most beautiful town and villages. The apartment was really characteristic but also full of comfort; we had everything we need... and don't forget to ask Leonardo, the very nice owner, some information on the history of Florence or suggestion on the best Tuscany wines!!

Match: Swimming pool

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Price per night from

$160

5 bedroom villa with pool in Tuscany

Impruneta house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

Match: Swimming pool

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Price per night from

$1,220

Relax in the countryside, 9 kms to Florence 3+2

Strada in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$136

Villa la Mandragola

San Casciano in Val di Pesa villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,233

Podere Campriano WINERY HOTEL "Suite Ele"

Greve in Chianti b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 10 minutes

Match: Swimming pool

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Price per night from

$160

Junior suite in the Mannor House

San Polo in Chianti house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 49 minutes

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Price per night from

$117

Podere Campriano WINERY HOTEL "Suite Vale"

Greve in Chianti b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 10 minutes

Match: Swimming pool

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Price per night from

$160

Casale Tignano

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$390

Villa il Castellaccio in Greve in Chianti Flat #2

Greve in Chianti house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$172

House Katia A

San Donato in Poggio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Swimming pool

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Price per night from

$206

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$136

Podere Vignola farmhouse near Florence - Torretta

Florence house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$233

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$553

Vichiaccio - Il Fienile

Campoli in Chianti farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Swimming pool

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Price per night from

$172

Castle in Chianti with private swimming pool, 15 minutes drive from Florence!

San Casciano in Val di Pesa villa

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 15

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Price per night from

$1,369

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

Match: Swimming pool

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Price per night from

$295

Il Capriolo sleeps 4 + 1 (on request)

San Polo in Chianti villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

Match: Swimming pool

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Price per night from

$246

Villa Daria

Vicchio house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$225

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