Castel San Gimignano Vacation Rentals from CA $91: Short-Term Rentals for 2025

Q: What are some of the best vacation rentals in Castel San Gimignano?

Beautiful stone house with garden and private pool. : This vacation home rental outside of Castel San Gimignano is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

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Vacation Rentals in Castel San Gimignano

Enjoy a selection of beverages and sweet treats in our bar area, featuring a variety of bottles, glasses, and a display case of pastries.

"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."

CA $105 total

includes taxes & fees

Aug 21 - Aug 22

Relax in the stylish lobby with comfortable sofas, a glass coffee table, and a beautiful view of the surrounding area.

"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."

CA $135 total

includes taxes & fees

Aug 19 - Aug 20

Step into Il Battistero, a charming coffee shop with a welcoming atmosphere and a variety of beverages.

"Excellent staffing, nice facility and great location"

CA $231 total

includes taxes & fees

Jul 31 - Aug 1

Relax by the serene pool surrounded by lush greenery and well-maintained hedges.

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

Relax by the pool surrounded by a white picket fence.

"Nothing wrong here! Fantastic, professional staff that took care of all our needs and always went the extra mile. Fantastic chef with great food and lovely “can help” attitude. Prestine pool! Would book again"

CA $203 total

includes taxes & fees

Jul 31 - Aug 1

Enjoy a compact kitchen with microwave, oven, and dishwasher, plus a dining area and cozy living space.

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

CA $181 total

includes taxes & fees

Aug 5 - Aug 6

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"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."

CA $171 total

includes taxes & fees

Jul 31 - Aug 1

Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"

Enjoy dining al fresco on this scenic outdoor terrace with a table set amidst a serene natural backdrop.

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

CA $126 total

includes taxes & fees

Aug 5 - Aug 6

Experience the grandeur of this beautifully decorated room, featuring intricate frescoes, plush seating, and classical artwork.

"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. "

Enjoy a serene city view from the comfort of your room, where a beautifully set table invites you to a soothing tea experience.

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

CA $266 total

includes taxes & fees

Aug 27 - Aug 28

Traditional stone building with a charming entrance, surrounded by potted plants and a wooden door.

"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."

Relax by the serene pool surrounded by lush greenery and rolling hills.

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

Escape to a serene garden setting with a charming stone building, surrounded by lush flowering plants and a meandering stone pathway.

"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"

Relax by the pool with a clear view of the surrounding landscape, surrounded by six lounge chairs and umbrellas.

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

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

Classic hotel room with a large bed, sitting area, and dining space.

"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!"

CA $195 total

includes taxes & fees

Aug 5 - Aug 6

CA $163 total

includes taxes & fees

Jul 31 - Aug 1

Relax by the serene pool surrounded by lush green hills and steps leading into the water.

"Wow! The property is just amazing! Located on a vineyard, it is in close proximity to everything. (Sienna, San Gimignano, Castelina di Chianti) The appartment was roomy and great for a family of 4. The view is spectacular and the restaurant has great service and food. I recommend without hesitation."

CA $358 total

includes taxes & fees

Aug 3 - Aug 4

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Top Castel San Gimignano Hotel Reviews

Hotel Athena

10/10 Excellent

"Staff was incredible - 10 minute walk to everything. Highly recommend! Especially loved front desk crew and Robert in the restaurant. "

Hotel Borgo di Cortefreda Relais

10/10 Excellent

"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."

Hotel Certosa Di Maggiano

10/10 Excellent

"A perfect place to stay. Nothing was too much trouble. Stunning views. Great facilities including a swimming pool and tennis court and a fabulous place to relax. Food & refreshments excellent. Easy distance from Florence and neighbouring villages. A wonderful place as a base to see much of Tuscany. "

La Certosa di Pontignano

10/10 Excellent

"Our stay at La Certosa di Pontignano was a truly memorable experience. The historic charm of the property combined with the serene Tuscan landscape creates a magical and peaceful atmosphere that’s hard to match. The rooms were comfortable, the grounds beautifully maintained, and the staff welcoming and attentive. While we did encounter a small issue during our stay, it was addressed promptly and resolved to our complete satisfaction, which we greatly appreciated. The overall experience far outweighed this minor hiccup. The historical significance of the location adds a special depth to the visit—walking through centuries-old cloisters and gardens while enjoying the beauty of Tuscany is something we won’t forget. We would gladly return and highly recommend it to anyone looking for a unique and tranquil retreat."

Poderi Arcangelo

10/10 Excellent

"Exceptional views from this property. The room was for 4. It had a rustic farm house vibe. Unfortunately there was mold in the bathroom and a nest of spiders in the beams above the bed (which my husband was happy to sleep under - so we ignored). There is no noise insulation between floors and you can hear other guests above you, but everyone was respectful and noise minimal. The spare blankets in the cupboard needed a wash and were unusable. Otherwise room was clean and comfortable. The infinity pool was great and generally quiet creating a relaxing atmosphere. You need a car if you stay in one of the annexes otherwise you would have to walk up a hill. We had access to a balcony and a common area. The kitchen was accessible but you are not allowed to use unless you book an apartment.) Breakfast was very good and the terrace is amazing. We only had interaction with two staff members. One was lovely, friendly and helpful. The other was the complete opposite, which ruined some of the shine. Overall lovely place to stay, fantastic grounds and we will definitely try and visit again!"

Find out more about Castel San Gimignano

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

Castel San Gimignano vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castel San Gimignano vacation rentals we have selected for you start as low as CA $91 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 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 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 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 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.

Frequently asked questions

Can I find a vacation rental in Castel San Gimignano?

Yes, we have vacation rentals close to top local attractions 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 coffeehouses 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 vacation rentals in Castel San Gimignano?

Beautiful stone house with garden and private pool.: This vacation home rental outside of Castel San Gimignano is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Castel San Gimignano?

With 5 Expedia vacation rentals, you're sure 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 larger area, you’ll find Sovestro in Poggio Winery and Piazza della Cisterna.

What are vacation rentals like in Castel San Gimignano?

Vacation rentals are privately owned accommodations you can book for several days or more in Castel San Gimignano. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.

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Castel San Gimignano Vacation Rentals

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Vacation Rentals in Castel San Gimignano

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

ApartHotel Anghel

ApartHotel Anghel

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Camping Siena Colleverde

Camping Siena Colleverde

Chianti Village Morrocco

Chianti Village Morrocco

Regis Condo

Regis Condo

Villa San Filippo

Villa San Filippo

villa con vista panoramica

villa con vista panoramica

Tuscasì Aparthotel

Tuscasì Aparthotel

Castello di Montegufoni

Castello di Montegufoni

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

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

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

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

La Casa di Ines

La Casa di Ines

Riserva di Fizzano Residence

Riserva di Fizzano Residence

Relais Badia a Passignano

Relais Badia a Passignano

Top Castel San Gimignano Hotel Reviews

Hotel Athena

Find out more about Castel San Gimignano

Find out more about Castel San Gimignano

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