Castelfalfi Holiday Rentals from AU$81: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Castelfalfi has to offer?

Calanchi Apartments : This holiday home rental outside Castelfalfi offers an outdoor pool, a rooftop terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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Our top choices for Castelfalfi holiday rentals

1. Tenuta Sant'Ilario

Gambassi Terme

Sergio

includes taxes & fees

6 Sept - 7 Sept

2. Antica Dimora Leones

Palaia

Brendan

includes taxes & fees

17 Aug - 18 Aug

3. 2bed, 1bath Garden apt in Chianti!

Frazione Mura, Montaione

Cayit A.

includes taxes & fees

17 Aug - 18 Aug

4. La Casina of Via Cresci, 14

Montaione

Jo P.

includes taxes & fees

9 Aug - 10 Aug

5. Tenuta Quadrifoglio

Gambassi Terme

Geraldine

includes taxes & fees

7 Sept - 8 Sept

6. B&B Il Moscondoro

Montopoli in Val d'Arno

Davide

includes taxes & fees

8 Aug - 9 Aug

7. Casa Vacanze Le Case

San Gimignano

Jackie

includes taxes & fees

28 Aug - 29 Aug

8. Borgo San Giusto

Empoli

Paul

includes taxes & fees

3 Sept - 4 Sept

9. Affittacamere e Ristorante Ariete

Ponsacco

"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."

Martina

includes taxes & fees

14 Aug - 15 Aug

10. Borgo Antico Residence

Certaldo Alto

jane

includes taxes & fees

8 Aug - 9 Aug

11. San Lorenzo by Interhome

Gambassi Terme

Dorota

includes taxes & fees

21 Aug - 22 Aug

12. DomuS Miniato

San Miniato

Celesta

includes taxes & fees

23 Aug - 24 Aug

13. Room Rent Morrona

Terricciola

Marzia

includes taxes & fees

12 Aug - 13 Aug

14. Apartment/ flat - Palaia

Palaia

Isabelle R.

includes taxes & fees

28 Aug - 29 Aug

15. Palazzo al Torrione 2

San Gimignano City Centre

Angel

includes taxes & fees

21 Aug - 22 Aug

Romantic Double Room, 1 Bedroom, Non Smoking | View from room

16. B&B Palazzo Tortoli

San Gimignano City Centre

Harold

includes taxes & fees

12 Aug - 13 Aug

17. AlbergoDiffusoVolterra

Volterra

Charles

includes taxes & fees

8 Aug - 9 Aug

18. Il Castello di San Ruffino

Casciana Terme Lari

daniel

includes taxes & fees

26 Aug - 27 Aug

19. Antico Borgo il Cardino

San Gimignano

Craig

includes taxes & fees

6 Sept - 7 Sept

20. Casa Vacanze Etrusco – Leccio Apartment

San Gimignano

includes taxes & fees

8 Aug - 9 Aug

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Top Castelfalfi Hotel Reviews

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Hotel Casolare Le Terre Rosse

10/10 Excellent

"This hotel is located in the most beautiful place in Tuscany. My husband and I were very impressed with the tranquility and picturesque beauty we were awed by daily. The staff are very friendly, the food is fabulous and it was just the perfect environment to explore wineries and castles or just lay back having a cocktail and swimming in their pool."

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Find out more about Castelfalfi

Everything you need to know about Castelfalfi holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castelfalfi holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castelfalfi holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Castelfalfi holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castelfalfi. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castelfalfi holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castelfalfi holiday rentals we have selected for you start as low as AU$81 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Castelfalfi rentals

At Expedia, we put the best Castelfalfi holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castelfalfi rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castelfalfi holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castelfalfi. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 are some of the best holiday rentals that Castelfalfi has to offer?

Calanchi Apartments: This holiday home rental outside Castelfalfi offers an outdoor pool, a rooftop terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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 Agricola Tamburini Emanuela.

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.

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Check prices for these dates

Our top choices for Castelfalfi holiday rentals

1. Tenuta Sant'Ilario

2. Antica Dimora Leones

3. 2bed, 1bath Garden apt in Chianti!

4. La Casina of Via Cresci, 14

5. Tenuta Quadrifoglio

6. B&B Il Moscondoro

7. Casa Vacanze Le Case

8. Borgo San Giusto

9. Affittacamere e Ristorante Ariete

10. Borgo Antico Residence

11. San Lorenzo by Interhome

12. DomuS Miniato

13. Room Rent Morrona

14. Apartment/ flat - Palaia

15. Palazzo al Torrione 2

16. B&B Palazzo Tortoli

17. AlbergoDiffusoVolterra

18. Il Castello di San Ruffino

19. Antico Borgo il Cardino

20. Casa Vacanze Etrusco – Leccio Apartment

Find holiday rentals that suit your style

Top Castelfalfi Hotel Reviews

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Hotel Borgo San Luigi

Villa I Barronci Resort & Spa

Castelfalfi

Hotel Casolare Le Terre Rosse

Salvadonica - Borgo del Chianti

Villa Petriolo

Tenuta di Artimino Melia Collection

Fattoria di Vegi

Find out more about Castelfalfi

Frequently asked questions

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