Castelfalfi Holiday Rentals from NZ$150: Search Short-Term Rentals

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

Holiday house with private pool and fenced garden : This holiday home rental outside of Castelfalfi is located on a river, and has a fireplace, a patio and a BBQ 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 that 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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Holiday Rentals in Castelfalfi

"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."

includes taxes & fees

13 Sept - 14 Sept

Seasonal outdoor pool, pool umbrellas, pool loungers

"Amazing stuff above and beyond… Perfect relaxing location we will be back for sure Thanks for everyone work there…"

"Wonderful hosts, perfect location, comfortable and beautiful villa with lovely heated swimming pool and all amenities for all ages."

includes taxes & fees

21 Aug - 22 Aug

"It was a great experience. The villa was perfect. Hosts were amazing. "

"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."

Outdoor pool, pool umbrellas, pool loungers

"Beautiful property and surrounds. Room was exactly as described, highly recommended "

"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "

includes taxes & fees

1 Sept - 2 Sept

"-"

includes taxes & fees

30 Aug - 31 Aug

"Quiet place to stay"

"We were able to easily check in early & and received friendly helpful service. "

"Beautiful location!"

"We came for the second time to Villanovia and again enjoyed a fabulous week in a unique surrounding. Special thanks to our host Marco!"

"The Toscana village is great - so relaxing. The long stay owners are very friendly and helpful, as are the staff. The onsite bar/restaurant is good, as is the pool. There is a local town in easy walking distance with many old buildings, nice bars, and places to eat. On Saturdays there is a food market, so you can stock up on salads, fruits, vegetables, meats, and cheeses, etc. We can't wait to go back."

"We had another wonderful stay in Buti. Thank you again Marco."

"The location and views were absolutely spectacular! Alessandro was EXTREMELY helpful and accommodating. He helped arrange for chef and wine tasting at the villa and they were memorable. "

"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "

"Heerlijke 2 weken gehad, prima basic appartement waar je vriendelijk onthaalt word door Roberto. Jammer dat de bedden niet zo goed zijn en dat er geen tuintje is. Wij hebben dus gezellig op de stoep gezeten, waar iedere avond de mensen uit het dorp samen komen om te kaarten. Aan de achterkant van het huis is het zwembad, mooi en met fijne ligstoelen. Het kleine dorpje ligt echt centraal en samen met het dorpscafeetje en winkeltje een superplek! Wij hebben het met onze 2 kinderen heel fijn...

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Top Castelfalfi Hotel Reviews

Hotel Leon Bianco

10/10 Excellent

"Very beautiful spot in the heart of San Gimignano. Room was clean with all comforts. Staff has been very friendly and accommodating. To get here was a challenge and a bit difficult (use Google maps - Waze wouldn’t get us here) but it’s a lovely place to stay. "

Cappuccina Country Resort

10/10 Excellent

"Our suite was BEAUTIFUL! Decorated to a very high standard. We had our own terrace which was perfect. The restaurant was super accommodating as we had two fussy eaters with us (our children) they made them something that they would eat! Super grateful and the food was delish. Would recommend this beautiful hotel to everyone! Next time we stay we will make sure to try the pool! "

Boccioleto Resort&Spa

10/10 Excellent

"This hotel was a charming little place in Tuscany. We had a 2 bedroom apartment. The kitchen was fully equipped. Rooms were big with comfortable beds and modern. In Tuscany, mosquitoes are a thing but our apartment had mosquitoes plugs in each room. There was a shared laundry we could use. The outdoor pool was great with a lovely view, parking was free, reception staff were nice and buffet breakfast was delicious every morning. An amazing place to stay!"

Borgo Pignano Tuscany

10/10 Excellent

"Staying at Borgo Pignano was not just a vacation—it was a return to a slower, more meaningful way of living. Nestled high in the rolling Tuscan hills, this estate feels like a place out of time, where elegance, history, and nature blend seamlessly. From the moment we arrived, we were captivated by the sweeping views—olive groves, vineyards, and cypress trees stretching as far as the eye could see. The main villa, with its frescoed walls and centuries-old charm, set the tone for a stay that was both luxurious and deeply soulful. Every detail is thoughtful, from the refined, rustic design of the rooms to the organic bath products made right on the estate. We especially loved the infinity pool carved into the limestone—it offers one of the most stunning views in all of Tuscany. The food was exceptional—fresh, seasonal, and sourced from the property’s own biodynamic farm. Whether enjoying a multi-course meal at Villa Pignano or a wood-fired pizza under the stars at Al Fresco, every bite told a story of the land. But what truly made our stay unforgettable was the sense of peace and authenticity. The staff were gracious, warm, and quietly attentive—always there when you needed them, but never intrusive. Whether you’re exploring nearby hill towns, enjoying a wine tasting, or simply reading under the shade of an ancient oak, Borgo Pignano offers something rare: a space to reconnect—with nature, with beauty, and with yourself. If you’re dreaming of Tuscany, dream no further. "

Poderi Arcangelo

10/10 Excellent

"Our stay at Poderi Arcangelo in the rolling hills of San Gimignano was nothing short of magical. Surrounded by vineyards and olive groves, the views were the kind that stop you in your tracks – especially at sunset when the Tuscan hills glow gold. The food was exceptional every day, with authentic local flavours that made each meal a highlight. The staff were warm, welcoming and always tried their best to help, adding to the charm of the place. The location is perfect for exploring nearby treasures such as San Gimignano itself, Certaldo, and Volterra. One thing to note – a hire car is essential. Public transport is virtually non-existent here; we couldn’t get a bus at all and taxis, while available, were scarce and very expensive – we spent €400 on just three journeys. This isn’t the hotel’s fault, though it would have been helpful to know in advance. Also, while the property is beautiful, there’s no real indoor bar area for relaxing before or after dinner. There is an outdoor bar, but it only opens on weekends and closes at 18:00, so an early evening drink isn’t always possible. Despite this, we had seven days of bliss and would return in a heartbeat – next time with a hire car, ready to explore every corner of this stunning part of Tuscany. "

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 favorite 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 depends 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 NZ$150 per night. Entering your travel dates in the search wizard you might find 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.

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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?

Holiday house with private pool and fenced garden: This holiday home rental outside of Castelfalfi is located on a river, and has a fireplace, a patio and a BBQ 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 that 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 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.

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Castelfalfi Holiday Rentals

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Holiday Rentals in Castelfalfi

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

Il Castello di San Ruffino

Il Castello di San Ruffino

Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

La Casa di Ines

La Casa di Ines

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

Villa San Filippo

Villa San Filippo

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Palazzo Pacini

Palazzo Pacini

Il Frutteto

Il Frutteto

Beautiful apartment in San Gimignano - RoccaiaCasa'70

Beautiful apartment in San Gimignano - RoccaiaCasa'70

Easy Space

Easy Space

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Toscana Holiday Village

Toscana Holiday Village

TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA

TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

Castello di Montegufoni

Castello di Montegufoni

Apartment in Ancient Borgo Le Querce

Apartment in Ancient Borgo Le Querce

Apartment in Palazzo- Residence Giuly Rosselmini -Pool

Apartment in Palazzo- Residence Giuly Rosselmini -Pool

Resort with pool in Riparbella

Resort with pool in Riparbella

Top Castelfalfi Hotel Reviews

Hotel Leon Bianco

Find out more about Castelfalfi

Find out more about Castelfalfi

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Explore a world of travel with Expedia

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