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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In two weeks

In two months

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In four months

Holiday Rentals in Castel San Gimignano

Our top choices for Castel San Gimignano holiday rentals

"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

31 Aug - 1 Sept

"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

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

"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

24 Aug - 25 Aug

"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."

"Would 10/10 recommend this stay to a friend and would stay here again! Room was beautiful, location was perfect, and the staff is kind and helpful!"

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. "

"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

25 Aug - 26 Aug

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

Outdoor pool, pool umbrellas, pool loungers

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

"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."

"We stayed at the property for a week . From the amazing view to the beautiful Vila, we had a wonderful stay. Everything we needed to make the stay comfortable was supplied. We will be back ! "

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Top Castel San Gimignano Hotel Reviews

Hotel Athena

10/10 Excellent

"I can’t say enough good things about this hotel. The property is not quite as rustic as some of the others in Siena - it looks like it was updated inside about 10-15 years ago but it’s still in wonderful shape - just not quite rustic or very modern. Coming from a hotel the night before that was also wonderful but rustic I found the better AC and more modern interior amenities a welcome change. I was in a nice big room on the 8th floor with a stunning view from the window and a soaker tub and we loved it. The staff is what really makes this property stand out and why I’d not consider staying anywhere else in Siena next time I come. From the bellhop who parked my car and brought my luggage up - remembering our names two days later when he had to get the car. From the wonderful lady at the front desk who upgraded my room for a tiny fee when she found out we were on our honeymoon. They even got me a reservation that very same night (Saturday of Palio!) at a Osteria da Divo. "

Hotel Borgo di Cortefreda Relais

10/10 Excellent

"We had a great experience to stay at this hotel. It was clean, friendly service, amazing restaurant and a fantastic swimming pool. We were with 2 kids and the room was big and great views. Everything was stocked in the room everyday, including the pool towels. I would highly recommend it. "

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

Our top choices for Castel San Gimignano holiday rentals

ApartHotel Anghel

ApartHotel Anghel

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Camping Siena Colleverde

Camping Siena Colleverde

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

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

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

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

Regis Condo

Regis Condo

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

Villa San Filippo

Villa San Filippo

Castello di Montegufoni

Castello di Montegufoni

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

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

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

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

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

Top Castel San Gimignano Hotel Reviews

Hotel Athena

Find out more about Castel San Gimignano

Find out more about Castel San Gimignano

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions