A city with historic towers and a vineyard.

Castel San Gimignano Vacation Rentals

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Our top choices for Castel San Gimignano vacation rentals

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $233
CA $265 total
includes taxes & fees
Jul 26 - Jul 27
Antico Borgo il Cardino

Edera cozy house in Tuscan village

Edera cozy house in Tuscan village
Castel San Gimignano
Edera cozy house in Tuscan village

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is CA $139
CA $156 total
includes taxes & fees
Jul 31 - Aug 1
Palazzo Pacini

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $150
CA $214 total
includes taxes & fees
Aug 2 - Aug 3
Palazzo al Torrione 2

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is CA $202
CA $230 total
includes taxes & fees
Jul 26 - Jul 27
B&B Palazzo Tortoli

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $178
CA $203 total
includes taxes & fees
Aug 2 - Aug 3
Casa Vacanze Le Case

Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is CA $117
CA $136 total
includes taxes & fees
Jul 26 - Jul 27
Donna Nobile

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (86 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is CA $73
CA $85 total
includes taxes & fees
Aug 23 - Aug 24
Camping Boschetto Di Piemma

Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is CA $139
CA $161 total
includes taxes & fees
Aug 18 - Aug 19
Materia Rooms San Gimignano

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
The price is CA $131
CA $154 total
includes taxes & fees
Jul 30 - Jul 31
Villa San Filippo

san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi
San Gimignano City Centre
9.8 out of 10, Exceptional, (41 reviews)
"Beautiful location in San Gimignano! The owner was so attentive and provided great suggestions for our visit. Charming apartment that serviced all of are needs. Boboli bakery (25 yards from apartment) is amazing and a must! Enjoyable stay!"
United States
Curt G.
The price is CA $232
CA $329 total
includes taxes & fees
Jul 31 - Aug 1
san gimignano apartment in historical center, courtyard and fast free wifi

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is CA $255
CA $285 total
includes taxes & fees
Aug 6 - Aug 7
Villa Montecastello

Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is CA $167
CA $192 total
includes taxes & fees
Jul 26 - Jul 27
Affittacamere Le Ginestre

Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is CA $221
CA $248 total
includes taxes & fees
Jul 26 - Jul 27
Tenuta Quadrifoglio

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
San Gimignano City Centre
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
The price is CA $188
CA $410 total
includes taxes & fees
Jul 26 - Jul 27
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

San Gimignano full center apartment with fast wifi and courtyard.

San Gimignano full center apartment with fast wifi and courtyard.
San Gimignano City Centre
9.6 out of 10, Exceptional, (10 reviews)
"Our cosy little part of the palazzo was wonderful and our host sent us to an amazing array of restaurants. We had a wonderful time."
United States
Daniel T.
The price is CA $239
CA $373 total
includes taxes & fees
Jul 27 - Jul 28
San Gimignano full center apartment with fast wifi and courtyard.

Casa Vacanze Etrusco – Leccio Apartment

Casa Vacanze Etrusco – Leccio Apartment
San Gimignano
The price is CA $308
CA $316 total
includes taxes & fees
Jul 26 - Jul 27
Casa Vacanze Etrusco – Leccio Apartment

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is CA $236
CA $373 total
includes taxes & fees
Jul 30 - Jul 31
Borgo Il Poggiaccio

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is CA $245
CA $275 total
includes taxes & fees
Jul 26 - Jul 27
Tenuta Sant'Ilario

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is CA $346
CA $384 total
includes taxes & fees
Aug 7 - Aug 8
Riserva di Fizzano Residence
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castel San Gimignano Hotel Reviews

Find out more about Castel San Gimignano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Castel San Gimignano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Farmhouse in the heart of the real chiantishire: This vacation home rental outside of Castel San Gimignano is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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

With 3 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 Alta Val d'Elsa River Park. In the larger area, you’ll find Sovestro in Poggio Winery and Historical Torture Museum.

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.