Castiglione Rentals

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3,075 Houses

Fattoria di Arsicci, holiday house weekly rented.

Badia Tedalda villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 15

“Great house and surroundings in Badia Tedalda” We had a great time in this lovely located holiday house. A great swimming pool with a magnificant view. If you like a relaxed holiday this is the place. The lady who takes care of the house daily can also like to prepare a wonderfull dinner at the house. Reservation a few days in advance. Smashing Italian dishes !!!

Match: Freezer Games room Swing set or jungle gym Lakefront

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Price per night from

$272

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Casanuova di Cignano

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$115

Villa Camelia

Farneta house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$235

Villa Del Sole

Cortona villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 13

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$448

Villa Ginestra

Teverina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$361

Villa Magnolia

Teverina villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$476

Big & Bright Studio in Tuscany near Cortona - WiFi

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$74

Apartment Spiga, 3 Bedroom apartment in the Heart of Tuscany Hills

Volterra villa

  • 5 bedrooms
  • 1 bathroom
  • sleeps 6

“Wonderful!” My family and I just returned from a very relaxing week at La fonte and would definitely go back again. My parents, my husband, and my two boys stayed in the Spiga apartment. The weather was perfect, and we spent most of our days playing in the pool and taking bike rides from the house. We were greeted with some fresh eggs, pasta, fresh tomato sauce, and some of the best olive oil I have ever tasted (or smelled!). Katia and her family were all very nice and helpful. We went to Volterra and San Gimignano a few times and had gelato just about every night :) The boys were so happy at the house that we didn't travel more than that. We also lucked out and had the entire place to ourselves for the week we were there. We would highly recommend this place!

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$87

Sealing the Lecci Gurian Roberta - The Lime Tree

Terranuova Bracciolini farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$93

Sealing the Lecci Gurian Roberta - Cornflower

Terranuova Bracciolini farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$74

Villa Borgo delle Spighe- A nice country estate sets a wonderful scenery

Cignano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$875

Vernianello - Type B

Poggibonsi farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$204

Agriturismo Incrociata Greppia

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$195

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$121

Agriturismo Incrociata Granaio

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$136

Agriturismo Incrociata Dispensa

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$136

Chianti House, Residence Farmholiday Il Palazzo

Pergine Valdarno house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$99

Colline House, in Tuscany, Residence Il Palazzo

Pergine Valdarno house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$73

Villa Teresa

Cortona villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Games room, Swing set or jungle gym, Lakefront, Freezer

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Price per night from

$292

Melograno San Gimignano Apartment Pool

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$148

Room Apartment, Residence Villa Elena

Guardistallo townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 4 minutes

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$97

IL GELSO

San Pietro a Cegliolo farmhouse

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$432

Villa La Poventa

Cortona villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$504

Villa Monarca -Tuscany-

Torrita di Siena villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$1,481

Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$1,234

Ripostena-Melissa House 1

Casole d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$1,234

Responds fast! avg. 2 hours 10 minutes

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$406

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$2,380

Casa Leana, Heated Pool, Games Room & Fabulous Views

Anghiari villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

“Amazing!! This word sums up our stay!” We stayed in Casa Leana with some friends recently. This is a beautiful old house and is furnished to a very high standard with a mixture of modern and antique furniture - we felt really at home there with the lovely big lounge and TVs and DVD players in most bedrooms plus literally Hundreds of Dvds to watch. Once we managed to get through our long relaxing breakfasts, we loved the outdoor space there - we all enjoyed the heated pool and unbelievably, I particularly liked the play area where I spent many hours in the hammock when my kids were playing on the swings. When we could tear the children away from the house we had a few days out, one of which we spent in Rome which was fabulous - we caught the early train from arezzo and had a whole day there. A fairly long and tiring day but well worth it. We also had a day at a beach side resort called Cesenatico. All in all this place was a great find and the local towns and villages are beautiful and unspoiled with wonderfully old fashioned family run shops and restaurants and, of course, ice cream parlors. We all want to revisit as we did not manage to see half the things we anticipated - we are already making plans for next year's trip to this lovely house. Thanks again Leigh and Di for helping to make Nick's birthday celebrations so memorable!

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$532

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$3,085

B & B Le Piagge

Central Pisa b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$253

Casale La Rosa dei Venti

Caprese Michelangelo house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$556

Casale del Lago

San Casciano in Val di Pesa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$247

Villa Cristina, your wonderful Tuscan dream !!

Arezzo villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$732

Villa Martina

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$1,587

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$1,703

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

3 of 4 match: Lakefront, Freezer, Games room, Swing set or jungle gym

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Price per night from

$611

Viewing 38 of 3,075
rentals in Castiglione

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