Name: Monastero di Cortona Hotel & Spa
Price range: $453 total
Rating: 10

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino

Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ...

9.8/10 Exceptional! (39 reviews)

"Pros: From the first night it felt like home away from home. The kitchen was very well equipped. Plenty of cookware, glasses, and dishware. The pool was wonderful, though too cold to get into because it was too early in the season. The view from the pool was indescribable! We had two dinners prepared ..."

Reviewed on May 11, 2026

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Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$647 nightly

$721 total

Jun 19 - Jun 20

Total with taxes and fees

Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...

9.8/10 Exceptional! (235 reviews)

"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, ..."

Reviewed on May 14, 2026

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

$403 nightly

$453 total

Jun 8 - Jun 9

Total with taxes and fees

Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

10/10 Exceptional! (282 reviews)

"We had an amazing stay at the monastero di Cortona. The property is absolutely beautiful and impeccably maintained. The pool area is lovely and the views are unbelievable. The staff was super helpful and attentive- gave us recommendations for restaurants (and made reservations for us) and helped ..."

Reviewed on May 26, 2026

See all 6,499 properties in Castiglion Fiorentino

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino

Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ...

9.8/10 Exceptional! (39 reviews)

"Pros: From the first night it felt like home away from home. The kitchen was very well equipped. Plenty of cookware, glasses, and dishware. The pool was wonderful, though too cold to get into because it was too early in the season. The view from the pool was indescribable! We had two dinners prepared ..."

Reviewed on May 11, 2026

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia Tuscany

Book a stay at this family-friendly vacation home in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tennis ...

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ...

9.4/10 Exceptional! (144 reviews)

"Nice hotel - clean, good breakfast, perfect location. Would stay again!"

Reviewed on May 5, 2026

See all properties in Castiglion Fiorentino

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Agricola Buccelletti Winery

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

Municipal Art Gallery

You can study the exhibits at Municipal Art Gallery, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Archaeological Museum

You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.