South Florence Rentals

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163 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.

Match: Private outdoor pool (unheated)

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Price per night from

$334

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 outdoor pool (unheated)

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Price per night from

$617

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$988

Stunning Country Villa at Montefili in Greve, Chianti

Greve in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Private outdoor pool (unheated)

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Price per night from

$740

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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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

Match: Private outdoor pool (unheated)

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Price per night from

$988

San Romolo

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$211

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated)

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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: Private outdoor pool (unheated)

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Price per night from

$1,457

5 bedroom villa with pool in Tuscany

Impruneta house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,219

Villa la Mandragola

San Casciano in Val di Pesa villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,234

Casale Tignano

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$390

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$556

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

Match: Private outdoor pool (unheated)

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Price per night from

$1,375

Villa Daria

Vicchio house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$226

Podere Erica

San Donato in Poggio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,040

Unique private villa near Tavarnelle. 11 bedrooms, pool, SPA, A/C in the Chianti

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated)

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Price per night from

$1,695

Podere del Chianti luxury villa between Florence and Siena. Sleeps 12, pool, A/C

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,384

Castello Lorenzo, Heart of Tuscany, Renaissance Villa with Pool

San Casciano in Val di Pesa villa

  • 11 bedrooms
  • 9 bathrooms
  • sleeps 20

Responds fast! avg. 2 hours 14 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,597

Casale del Lago

San Casciano in Val di Pesa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$247

Villa Martina

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,586

The Villa

San Casciano in Val di Pesa villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$975

Anticopozzo

Poggibonsi house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$488

Poggio Ridente

Barberino Val d'Elsa house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$699

Amaranta House

Greve in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$222

Torre del Santo

Barberino Val d'Elsa villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated)

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Price per night from

$2,803

The Angolino

Radda in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$263

House with pool surrounded of a large park near Old Florence City Center

Florence house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$617

the Casalone

Greve in Chianti house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$283

Villa Lante

Borgo San Lorenzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$562

Villa Belvedere

Poggibonsi villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,340

Villa Tizzano

Greve in Chianti villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$3,347

Vignalsole

Radda in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated)

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Price per night from

$791

BREATHTAKING 9BD-7BA VILLA IN TUSCANY W/POOL, 9 MILES FROM FLORENCE!

Bagno a Ripoli villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated)

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Price per night from

$1,851

Villa RoseDelChianti, amazing country & cooking

Figline e Incisa Valdarno villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$441

Villa Vicchio Villa Vicchio

Vicchio villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$414

Casale Classico Casale Classico plus Dependance

San Casciano in Val di Pesa apartment

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated)

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Price per night from

$1,409

Luxury villa close Florence in the Chianti area. 8 bedrooms with pool, Il Forte!

Bagno a Ripoli villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated)

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Price per night from

$986

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