Castel San Gimignano Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $174
CA $199 total
includes taxes & fees
Apr 27 - Apr 28
Antico Borgo il Cardino

Giovanna apartment on two levels overlooking the swimming pool

Giovanna apartment on two levels overlooking the swimming pool
Castel San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect - the best is this wonderful Garden with the views in the toscana"
Germany
Antje F.
Giovanna apartment on two levels overlooking the swimming pool

Simona delightful studio apartment with pool view

Simona delightful studio apartment with pool view
Castel San Gimignano
9.8 out of 10, Exceptional, (7 reviews)
"Perfect stay"
Germany
Marcel H.
Simona delightful studio apartment with pool view

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is CA $163
CA $184 total
includes taxes & fees
Apr 26 - Apr 27
Casa di Campagna in Toscana

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is CA $137
CA $157 total
includes taxes & fees
May 22 - May 23
Il Pozzo di Sant'Andrea

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
The price is CA $186
CA $210 total
includes taxes & fees
Apr 27 - Apr 28
Tenuta Sant'Ilario

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is CA $225
CA $252 total
includes taxes & fees
Apr 26 - Apr 27
Villa Montecastello

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is CA $242
CA $271 total
includes taxes & fees
May 8 - May 9
Antico Borgo Poggiarello

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is CA $278
CA $309 total
includes taxes & fees
May 17 - May 18
Riserva di Fizzano Residence

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $101
CA $132 total
includes taxes & fees
Apr 28 - Apr 29
Tuscasì Aparthotel

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 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 $159
CA $289 total
includes taxes & fees
May 21 - May 22
Borgo Il Poggiaccio

Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is CA $228
CA $258 total
includes taxes & fees
May 19 - May 20
Residence Borgo San Lorenzo a Linari

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is CA $1,139
CA $1,266 total
includes taxes & fees
May 14 - May 15
Villa Marcolina

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is CA $209
CA $302 total
includes taxes & fees
Apr 28 - Apr 29
Chianti Craft House Badia a Passignano

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (200 reviews)
"Excellent B&B, very helpful host"
United States
Anushya
The price is CA $162
CA $185 total
includes taxes & fees
Apr 29 - Apr 30
B&B Il Corso

Villa Mucellena

Villa Mucellena
Casole d'Elsa
The price is CA $140
CA $157 total
includes taxes & fees
Apr 28 - Apr 29
Villa Mucellena

Antica Dimora Leones

Antica Dimora Leones
Palaia
9.0 out of 10, Wonderful, (16 reviews)
"Wonderful and unique place to stay. Staff were terrific. The church bells ring through the night so bring earplugs if you’re a light sleeper!"
Canada
Brendan
The price is CA $93
CA $109 total
includes taxes & fees
May 10 - May 11
Antica Dimora Leones

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is CA $141
CA $162 total
includes taxes & fees
Apr 26 - Apr 27
Fullino Nero

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (36 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is CA $212
CA $240 total
includes taxes & fees
Apr 29 - Apr 30
La Locanda di Pietracupa

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is CA $201
CA $227 total
includes taxes & fees
May 18 - May 19
La Coroncina Lodging
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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.