Castel San Gimignano Holiday Rentals from €76: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Castel San Gimignano has to offer?

Holiday house with private pool and fenced garden : This holiday home rental outside of Castel San Gimignano 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 Castel San Gimignano

"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

24 Aug - 25 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

Panoramic Suite, City View | View from room

"Beautiful, unique property in central Siena. Sonia at reception was excellent! "

includes taxes & fees

30 Aug - 31 Aug

"Safe, great proximity to Siena without being too close, nice pool."

"Excellent staffing, nice facility and great location"

includes taxes & fees

25 Aug - 26 Aug

"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

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

Grand Apartment with Garden | Private kitchen

"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."

Seasonal outdoor pool, pool umbrellas, pool loungers

"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."

"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. "

includes taxes & fees

23 Aug - 24 Aug

Outdoor pool, pool umbrellas, pool loungers

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

"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 company retreat at this amazing location. Everyone was in love with the place and the facilities!"

"Perfect location for a family reunion with our adult children and their partners. We had a wonderful time."

"Quiet place to stay"

"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

6 Sept - 7 Sept

"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"

"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

"We enjoyed a relaxing week in this beautiful apartment surrounded by lush gardens with a view of the Tuscan hills. Our host was charming and welcoming. "

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Top Castel San Gimignano Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"On our last night there the gentleman in the foyer was amazing thankyou "

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"My wife and I had a wonderful time. The hotel is spacious, nice and clean, as you would expect at a 5 star hotel. The location couldn’t be better. Hotel personnel is highly professional. You won’t find a better place to have breakfast than at the hotel. "

La Certosa di Pontignano

10/10 Excellent

"This was a great place. The place is well thought through and has a great vibe to it. It's a very good mix of ancient and modern part brought together. The walk across both the courtyards is calming. The chapel is peaceful. We got to stay both in the old and the new parts. The old part is good and will be great in good weather with a good group. The staff are really amazing and understanding. With our little one , they were very accommodating - esp the restaurant staff. We will go back in cooler weather once again "

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. "

Palazzo Ravizza

10/10 Excellent

"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with me for a very long time. "

Find out more about Castel San Gimignano

Everything you need to know about Castel San Gimignano 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 Castel San Gimignano holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Castel San Gimignano holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castel San Gimignano holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castel San Gimignano. 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 Castel San Gimignano 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 Castel San Gimignano holiday rentals we have selected for you start as low as €76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castel San Gimignano rentals

At Expedia, we put the best Castel San Gimignano 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 Castel San Gimignano 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 Castel San Gimignano 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 Castel San Gimignano. 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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All accommodation types in Castel San Gimignano

Farmstay in Castel San Gimignano

Frequently asked questions

Can I find a holiday rental in Castel San Gimignano?

Yes, there are holiday rentals close to the most popular sights in Castel San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Castel San Gimignano is known for its coffee shops and local tours. Make sure you have time to check out the wineries while you're in the area.

What are some of the best holiday rentals that Castel San Gimignano has to offer?

Holiday house with private pool and fenced garden: This holiday home rental outside of Castel San Gimignano 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 Castel San Gimignano?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Castel San Gimignano stay.

What can I see and do in Castel San Gimignano?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Sentierelsa Trail. In the wider area, you’ll find Sovestro in Poggio Winery and Piazza della Cisterna.

What are holiday rentals like in Castel San Gimignano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castel San Gimignano. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for families.

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Holiday Rentals in Castel San Gimignano

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Holiday Rentals in Castel San Gimignano

ApartHotel Anghel

Camping Boschetto Di Piemma

Residenza d'Epoca Palazzo Borghesi

Camping Siena Colleverde

Il Battistero Siena - Residenza d'Epoca

Villa with large garden in the Chianti hills

Holiday house with private pool and fenced garden

Regis Condo

Villa San Filippo

Castello di Montegufoni

La Casa di Ines

Castello Del Nero - Podere San Filippo

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

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

Beautiful apartment in San Gimignano - RoccaiaCasa'70

Riserva di Fizzano Residence

Beautiful stone house with garden and private pool.

panoramica casa con piscina privata

A wonderful country house in the heart of Chianti

Top Castel San Gimignano Hotel Reviews

Hotel Chiusarelli

Hotel Athena

Grand Hotel Continental Siena – Starhotels Collezione

La Certosa di Pontignano

Hotel Borgo di Cortefreda Relais

Poderi Arcangelo

Palazzo Ravizza

Hotel Certosa Di Maggiano

Villa Scacciapensieri Boutique Hotel

Find out more about Castel San Gimignano

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Frequently asked questions