Montecastelli Holiday Rentals from NZ$117: Search Short-Term Rentals

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

Holiday house with private pool and fenced garden : This holiday home rental outside of Montecastelli 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 Montecastelli

Our top choices for Montecastelli holiday rentals

"We all had a wonderful holiday. The villa was lovely and so well equipped. The garden, hot tub and especially the pool were amazing!! Gina and Franco were so kind to bring us wonderful treats during the stay and left a very generous welcome basket. Absolutely fantastic place for a holiday. We hope to return one day!"

"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."

includes taxes & fees

26 Aug - 27 Aug

"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

"Cute rustic cottage with a beautiful restful view of farm land and forrested hills and a covered outdoor eating area."

"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."

includes taxes & fees

15 Sept - 16 Sept

"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. "

"Very clean and comfortable accommodations. Beautiful view of the countryside!"

includes taxes & fees

16 Sept - 17 Sept

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

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

includes taxes & fees

25 Aug - 26 Aug

includes taxes & fees

31 Aug - 1 Sept

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

"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."

Outdoor pool, pool umbrellas, pool loungers

"We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here."

includes taxes & fees

26 Aug - 27 Aug

"Great place to stay with family/friends. The grounds are beautiful and immaculately maintained. The house is spotless. The owners organized a meal and a cooking class at the villa for us. They were willing and able to help in any way possible and were very organized with the check in and check out process. Will definitely return. "

"Quiet place to stay"

"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"

"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"

includes taxes & fees

16 Sept - 17 Sept

"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....

includes taxes & fees

1 Sept - 2 Sept

"Appartamento ben arredato con grande terrazza e vista magnifica sulle colline. Ho apprezzato molto cenare fuori alla luce della luna piena e approfittare sin dal mattino della bella atmosfera. La piscina è molto vicina e Gina è stata fantastica ad accoglierci e darci consigli dall'inizio alla fine del nostro soggiorno. Grazie e a presto! "

"Musty room, lots of bugs, damp, uncomfortable bed"

includes taxes & fees

18 Sept - 19 Sept

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Top Montecastelli Hotel Reviews

Borgo Pignano Tuscany

10/10 Excellent

"La estadia en Borgo P. fue una total experiencia. Definitivamente es uno de los hoteles mas exclusivos de la Toscana. La propiedad es deslumbrante, las areas comunes , terrazas y habitaciones están impecables. El hotel esta apartado y solo podrás llegar en auto pero vale la pena 200%. A nuestra llegada nos recibieron con bebidas y toallas refrescantes (fuimos en Agosto)(pero la temperatura agradable pues esta en lo alto de una montana) Vittorio nos recibió y nos dio un Tour por todo el hotel fue super amable y para el Check in, no tuvimos que estar parado frente al front desk. En la habitación teníamos una nota personalizada de bienvenida escrita a mano, uvas y vino. Room espacioso al igual que el baño, con body wash, shampoo y conditioner del mismo brand del hotel donde todo es elaborado artesanalmente por ellos mismos, simplemente un WAO. Te hacen sentir muy a gusto y como en familia. J. Luigi en el bar super amable y atento a nuestra familia. Sr. Gigi se tomo el tiempo de darnos un tour privado en un Golf Car por toda la propiedad y pudimos visitar sus huertos de vegetales. La miel es producida por ellos mismos y también crian cerdos, gallinas, y conejos para su autoabastecimiento. Hay Agua y Cafe es gratis en el hotel 24 hrs. Cenamos en La Terraza al atardecer y la comida deliciosa. Recomendamos este hotel 100%. Los atardeceres son increíbles. Gracias a Borgo por la experiencia. Pronto regresaremos. Sus 2 piscinas son espectaculares con unas vistas que nunca olvidaras."

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! "

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 Montecastelli

Everything you need to know about Montecastelli 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 Montecastelli 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 Montecastelli holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecastelli holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecastelli. 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 Montecastelli 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 Montecastelli holiday rentals we have selected for you start as low as NZ$117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli 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 Montecastelli 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 Montecastelli 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 Montecastelli. 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 Montecastelli?

Yes, there are holiday rentals close to the most popular sights in Montecastelli, or you can select a more secluded option if you're looking for a relaxing stay.

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

Holiday house with private pool and fenced garden: This holiday home rental outside of Montecastelli 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.

How many holiday rentals will I find in Montecastelli?

Expedia has 14 holiday rentals for your stay in Montecastelli.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Terre di Vini, or get out into nature at a spot like Alta Val d'Elsa River Park. In the wider area, you’ll find Medici Fortress and Etruscan Museum.

What are holiday rentals like in Montecastelli?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montecastelli. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family getaway.

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Montecastelli Holiday Rentals

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Holiday Rentals in Montecastelli

Our top choices for Montecastelli holiday rentals

Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday

Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday

ApartHotel Anghel

ApartHotel Anghel

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

agriturismo la roggiola

agriturismo la roggiola

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

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

Tuscasì Aparthotel

Tuscasì Aparthotel

Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

Palazzo Pacini

Palazzo Pacini

La Casa di Ines

La Casa di Ines

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

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

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Riserva di Fizzano Residence

Riserva di Fizzano Residence

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

Beautiful apartment in San Gimignano - RoccaiaCasa'70

Beautiful apartment in San Gimignano - RoccaiaCasa'70

Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Residence Il Paradiso

Residence Il Paradiso

panoramica casa con piscina privata

panoramica casa con piscina privata

Watching The Horizon in residence with swimming pool for a fee

Watching The Horizon in residence with swimming pool for a fee

Borgo Il Poggiaccio

Borgo Il Poggiaccio

Top Montecastelli Hotel Reviews

Borgo Pignano Tuscany

Find out more about Montecastelli

Find out more about Montecastelli

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