Castel San Gimignano Vacation Rentals

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Our top choices for Castel San Gimignano vacation rentals

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 $110
CA $126 total
includes taxes & fees
Mar 9 - Mar 10
Tuscasì Aparthotel

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 $132
CA $152 total
includes taxes & fees
Mar 11 - Mar 12
Il Pozzo di Sant'Andrea

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is CA $129
CA $149 total
includes taxes & fees
Mar 4 - Mar 5
La Coroncina Lodging

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is CA $131
CA $182 total
includes taxes & fees
Mar 10 - Mar 11
Antica Pieve B&B

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (8 reviews)
"Love this town. Location is great "
United States
William
The price is CA $113
CA $133 total
includes taxes & fees
Apr 1 - Apr 2
La Casa di Ines

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is CA $104
CA $117 total
includes taxes & fees
Mar 8 - Mar 9
Chianti Village Morrocco

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
Casa di Campagna in Toscana

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239 reviews)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is CA $186
CA $212 total
includes taxes & fees
Mar 8 - Mar 9
Fullino Nero

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (98 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is CA $160
CA $180 total
includes taxes & fees
Mar 4 - Mar 5
Palazzo Pacini

B&B Le Dimore Mezza Costa

B&B Le Dimore Mezza Costa
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (25 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is CA $108
CA $125 total
includes taxes & fees
Mar 10 - Mar 11
B&B Le Dimore Mezza Costa

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

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 $240
CA $269 total
includes taxes & fees
Mar 24 - Mar 25
Antico Borgo Poggiarello

Blueyes House Tuscany

Blueyes House Tuscany
Montespertoli
The price is CA $141
CA $185 total
includes taxes & fees
Mar 17 - Mar 18
Blueyes House Tuscany

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
Tenuta Quadrifoglio

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (9 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 $237
CA $333 total
includes taxes & fees
Mar 4 - Mar 5
Chianti Craft House Badia a Passignano

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $149
CA $172 total
includes taxes & fees
Mar 6 - Mar 7
Casa Vacanze Le Case

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is CA $183
CA $208 total
includes taxes & fees
Mar 8 - Mar 9
Agriturismo La Ferrozzola

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (193 reviews)
"Great location"
United Kingdom
Mina
B&B Il Corso
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?

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms : This vacation home rental outside of Castel San Gimignano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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 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 Val di Merse. 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.