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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Castelfalfi holiday rentals

Outdoor dining

Affittacamere e Ristorante Ariete

Affittacamere e Ristorante Ariete
Ponsacco
9.0 out of 10, Wonderful, (2 reviews)
"This place is a bit further out from Pisa, but we still had a really nice stay and made the most of it. It’s great value for money, which was a big plus. The hotel itself is a little old-fashioned, but honestly, the staff more than made up for it—they were super friendly and welcoming the whole time. The restaurant was also a highlight, with really tasty food that we enjoyed a lot. It’s a good spot if you’ve got a car and want to explore the nearby villages and surrounding area."
United Kingdom
Martina
The price is 2.255.367 ₫
2.480.904 ₫ total
includes taxes & fees
15 May - 16 May
Affittacamere e Ristorante Ariete
Deluxe Apartment, 1 Bedroom | Minibar, in-room safe, laptop workspace, soundproofing

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (41 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is 3.721.216 ₫
4.186.368 ₫ total
includes taxes & fees
15 May - 16 May
Borgo San Giusto
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is 6.159.797 ₫
6.899.817 ₫ total
includes taxes & fees
12 May - 13 May
Villa il Fedino
Triple Room | Room service – dining

B&B Il Moscondoro

B&B Il Moscondoro
Montopoli in Val d'Arno
8.0 out of 10, Very good, (8 reviews)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is 2.678.035 ₫
2.945.963 ₫ total
includes taxes & fees
12 May - 13 May
B&B Il Moscondoro
View from property

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is 3.523.992 ₫
4.620.511 ₫ total
includes taxes & fees
15 May - 16 May
Antica Pieve B&B
Property entrance

Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very good, (21 reviews)
"Very basic lodgings - simple but good location between Florence & Pisa. Breakfast place right underneath the rooms made breakfast convenient. Parking was super simple & across the street, which is rare in Italy. "
United States
Scott
The price is 2.033.567 ₫
2.329.953 ₫ total
includes taxes & fees
15 May - 16 May
Affittacamere a 20 minuti da Firenze
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is 2.311.028 ₫
2.604.150 ₫ total
includes taxes & fees
17 May - 18 May
Chianti Village Morrocco
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (61 reviews)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
The price is 3.669.063 ₫
4.191.020 ₫ total
includes taxes & fees
12 May - 13 May
B&B Palazzo Tortoli
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.031.318 ₫
4.589.501 ₫ total
includes taxes & fees
13 May - 14 May
Antico Borgo il Cardino
Seasonal outdoor pool, pool umbrellas, pool loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (41 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
The price is 1.844.540 ₫
2.215.055 ₫ total
includes taxes & fees
13 May - 14 May
Villa San Filippo
Garden

Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (17 reviews)
"Wonderful and unique place to stay. Staff were terrific. The church bells ring through the night so bring earplugs if you’re a light sleeper!"
Canada
Brendan
The price is 1.736.424 ₫
2.034.107 ₫ total
includes taxes & fees
17 May - 18 May
Antica Dimora Leones
Breakfast, lunch, dinner served; Regional cuisine

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (36 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is 4.418.944 ₫
4.984.879 ₫ total
includes taxes & fees
14 May - 15 May
La Locanda di Pietracupa
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is 3.722.457 ₫
4.187.609 ₫ total
includes taxes & fees
18 May - 19 May
Tenuta Sant'Ilario
Comfort Room | Premium bedding, free WiFi

Room Rent Morrona

Room Rent Morrona
Terricciola
9.0 out of 10, Wonderful, (6 reviews)
"Ottima struttura "
Italy
Marzia
The price is 1.712.606 ₫
1.883.867 ₫ total
includes taxes & fees
12 May - 13 May
Room Rent Morrona
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is 2.911.017 ₫
4.132.423 ₫ total
includes taxes & fees
12 May - 13 May
Palazzo al Torrione 2
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is 3.344.753 ₫
3.741.372 ₫ total
includes taxes & fees
12 May - 13 May
Palazzo Pacini
Exterior

Il Castello di San Ruffino

Il Castello di San Ruffino
Casciana Terme Lari
9.2 out of 10, Wonderful, (30 reviews)
"Really cool experience to stay at a castle. Perfect destination for celebrations."
United States
daniel
The price is 2.867.104 ₫
3.277.855 ₫ total
includes taxes & fees
18 May - 19 May
Il Castello di San Ruffino
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is 4.564.692 ₫
5.114.191 ₫ total
includes taxes & fees
14 May - 15 May
Villa Montecastello
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is 1.370.084 ₫
1.569.112 ₫ total
includes taxes & fees
17 May - 18 May
Sportland
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is 3.347.685 ₫
3.837.504 ₫ total
includes taxes & fees
29 May - 30 May
Casa Vacanze Le Case
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.
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Top Castelfalfi Hotel Reviews

Villa Sabolini

Villa Sabolini

10/10 Excellent
"Beautiful hotel and amazing staff. I specifically want to call out Bruno (I believe that's his name) He was so helpful during our stay and went above and beyond to make us feel comfortable and gave us good tips to explore nearby. He even stayed late to help my husband with my birthday suprise. What a perfect stay in Tuscany and good in-house restaurant and beautiful location. "
Maria 2-night trip
Posted 3 hours ago
Villa Sabolini

Frequently asked questions

Are there holiday rentals in Castelfalfi?

Yes, there are holiday rentals close to the most popular sights in Castelfalfi, or you can select a more secluded option if you're looking for a relaxing stay. Castelfalfi is known for its golf courses and restaurants.

What can I see and do in Castelfalfi?

While exploring the area, visit family-friendly sights like Peccioli Prehistoric Park, or get outside and enjoy nature at Casciana Thermal Baths. In the wider area, you’ll find Castelfalfi Golf Course and Monastery of San Vivaldo.

What are holiday rentals like in Castelfalfi?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castelfalfi. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for small groups.