Castelfalfi Vacation Rentals from $55: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Castelfalfi?

Holiday house with private pool and fenced garden : This vacation home rental outside of Castelfalfi is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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Our top choices for Castelfalfi vacation rentals

A garden with a round table and wicker chairs under a tree.

1. Antica Dimora Leones

Palaia

Thomas

$56 nightly

Sep 3 - Sep 4

Total with taxes and fees

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

2. Tenuta Sant'Ilario

Gambassi Terme

Sergio

$137 nightly

Sep 6 - Sep 7

Total with taxes and fees

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

3. Borgo Antico Residence

Certaldo Alto

jane

$92 nightly

Aug 31 - Sep 1

Total with taxes and fees

A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

4. Borgo San Giusto

Empoli

Paul

$99 nightly

Aug 31 - Sep 1

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

5. Casa Vacanze Le Case

San Gimignano

Jackie

$124 nightly

Sep 17 - Sep 18

Total with taxes and fees

An outdoor brick barbecue area with a wooden bench nearby.

6. 2bed, 1bath Garden apt in Chianti!

Frazione Mura, Montaione

Cayit A.

$219 nightly

Sep 22 - Sep 23

Total with taxes and fees

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

7. AlbergoDiffusoVolterra

Volterra

Mia

$153 nightly

Sep 3 - Sep 4

Total with taxes and fees

A narrow street with buildings on either side, featuring stone walls and metal gates.

8. La Casina of Via Cresci, 14

Montaione

Jo P.

$119 nightly

Aug 30 - Aug 31

Total with taxes and fees

A view from a window overlooking a rural landscape with fields and a distant mountain range.

9. B&B Palazzo Tortoli

San Gimignano City Centre

Harold

$144 nightly

Aug 31 - Sep 1

Total with taxes and fees

A garden with a stone pathway, wooden benches, and various potted plants.

10. Antico Borgo il Cardino

San Gimignano

Craig

$156 nightly

Aug 30 - Aug 31

Total with taxes and fees

An arched entrance with a lantern above, flanked by two potted plants.

11. Villa il Fedino

San Casciano in Val di Pesa

"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...

Nilesh

$254 nightly

Aug 30 - Aug 31

Total with taxes and fees

A rectangular swimming pool with clear blue water, surrounded by a tiled deck.

12. 2-BR 1 bath abode in the Chianti hills!

Mura, Montaione

Anke G.

$217 nightly

Sep 6 - Sep 7

Total with taxes and fees

An open wooden door leading to an outdoor patio with a table and chairs.

13. Palazzo al Torrione 2

San Gimignano City Centre

Angela

$135 nightly

Sep 6 - Sep 7

Total with taxes and fees

14. Coppo – Apartment with Pool and Views of the Tuscan Hills

Gambassi Terme

$475 nightly

Sep 29 - Sep 30

Total with taxes and fees

A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

15. Room Rent Morrona

Terricciola

Marzia

$73 nightly

Sep 13 - Sep 14

Total with taxes and fees

A modern entrance with glass doors and a marble floor, leading into a well-lit interior.

16. Affittacamere a 20 minuti da Firenze

Empoli

Joshua

$55 nightly

Aug 30 - Aug 31

Total with taxes and fees

A table with a tray of pastries, a teapot, cups, and water bottles by a window with a view of greenery.

17. B&B Il Moscondoro

Montopoli in Val d'Arno

Davide

$90 nightly

Sep 14 - Sep 15

Total with taxes and fees

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

18. Palazzo Pacini

Colle di Val d'Elsa

John

$154 nightly

Sep 2 - Sep 3

Total with taxes and fees

A courtyard with outdoor seating, a brick building, and a tree.

19. 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

$66 nightly

Sep 12 - Sep 13

Total with taxes and fees

An outdoor barbecue area with a stone structure, a wooden cabinet, and a grill.

20. Apartment 'Sasso 3' with Private Terrace, Wi-Fi and Air Conditioning

San Gimignano

Anonymous traveler

$207 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Castelfalfi Hotel Reviews

Villa Sabolini

10/10 Excellent

"We couldn’t rate Villa Sabolini more highly - we had such an excellent time. It is a beautiful property and the perfect place to relax and enjoy Tuscany. The staff were so helpful and friendly too."

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

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Poderi Arcangelo

8/10 Good

"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."

Find out more about Castelfalfi

Everything you need to know about Castelfalfi vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castelfalfi vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castelfalfi vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castelfalfi in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $55 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castelfalfi rentals

At Expedia, we put the best Castelfalfi vacation 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 vacation.

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 vacation rentals in Castelfalfi?

Yes, we have vacation rentals close to top attractions in Castelfalfi, or you can select a more remote option if you want a relaxing place to stay. Castelfalfi is known for its golf courses and restaurants.

What are some of the best vacation home rentals in Castelfalfi?

Holiday house with private pool and fenced garden: This vacation home rental outside of Castelfalfi is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Castelfalfi?

While exploring the area, visit family-friendly sights like Pasta Martelli, or get outside and enjoy nature at Casciana Thermal Baths. In the larger area, you’ll find Castelfalfi Golf Course and Teatro del Silenzio.

What are vacation rentals like in Castelfalfi?

Vacation rentals are private properties you can book for several days or more in Castelfalfi. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip.

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Check prices for these dates

Our top choices for Castelfalfi vacation rentals

1. Antica Dimora Leones

2. Tenuta Sant'Ilario

3. Borgo Antico Residence

4. Borgo San Giusto

5. Casa Vacanze Le Case

6. 2bed, 1bath Garden apt in Chianti!

7. AlbergoDiffusoVolterra

8. La Casina of Via Cresci, 14

9. B&B Palazzo Tortoli

10. Antico Borgo il Cardino

11. Villa il Fedino

12. 2-BR 1 bath abode in the Chianti hills!

13. Palazzo al Torrione 2

14. Coppo – Apartment with Pool and Views of the Tuscan Hills

15. Room Rent Morrona

16. Affittacamere a 20 minuti da Firenze

17. B&B Il Moscondoro

18. Palazzo Pacini

19. Affittacamere e Ristorante Ariete

20. Apartment 'Sasso 3' with Private Terrace, Wi-Fi and Air Conditioning

Find vacation rentals that suit your style

Top Castelfalfi Hotel Reviews

Villa Sabolini

Hotel Sovestro

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

Poderi Arcangelo

Villa Petriolo

Park Hotel Chianti

Tenuta di Artimino Melia Collection

Hotel Da Vinci

Hotel Toscana Ambassador

Find out more about Castelfalfi

Frequently asked questions

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