Search Holiday Rentals in Castel San Gimignano

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Top Holiday Rentals in Castel San Gimignano

Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
The price is 2.460.061 ₫
3.623.583 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Palazzo al Torrione 2
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is 3.300.976 ₫
3.753.542 ₫ total
includes taxes & fees
8 Dec - 9 Dec
PALAZZO DEL PAPA
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (190)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Deluxe Apartment, City View | Living area | 24-inch flat-screen TV with digital channels, TV
Palazzo Lenzi

Palazzo Lenzi

Siena City Centre
9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is 4.836.947 ₫
5.442.956 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Palazzo Lenzi
Exterior
Sportland

Sportland

Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Birthday party area
Siena Vip

Siena Vip

Siena City Centre
9.2 out of 10, Wonderful, (419)
"A great location!"
Canada
Cheryl
Siena Vip
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room
B&B Palazzo del Magnifico

B&B Palazzo del Magnifico

Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is 4.475.617 ₫
5.045.494 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Residenza d'Epoca Palazzo Borghesi
Exterior detail
B&B Palazzo Tortoli

B&B Palazzo Tortoli

San Gimignano City Centre
9.2 out of 10, Wonderful, (57)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
The price is 3.485.977 ₫
3.987.469 ₫ total
includes taxes & fees
3 Dec - 4 Dec
B&B Palazzo Tortoli
Apartment, 2 Bedrooms | Premium bedding, down duvets, in-room safe, blackout curtains
Terre di Baccio

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
Terre di Baccio
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, pool loungers
Tenuta Sant'Ilario

Tenuta Sant'Ilario

Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Deluxe Apartment | Living area | 50-inch Smart TV with cable channels
Casa Ciseri

Casa Ciseri

Siena City Centre
9.8 out of 10, Exceptional, (9)
"Beautiful property in the center of Siena! "
United States
Maura
The price is 6.866.320 ₫
7.675.267 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Casa Ciseri
Exterior
The Balcony Suite -Piazza del Campo View

The Balcony Suite -Piazza del Campo View

Siena City Centre
9.2 out of 10, Wonderful, (15)
"Beautiful Apartment in the Piazza del campo. Location is outstanding. Very spacious and comfortable."
Canada
Jatinder
The price is 3.918.973 ₫
4.524.922 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Balcony Suite -Piazza del Campo View
Gazebo
Domus il Palio B&B

Domus il Palio B&B

Ravacciano
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B
Comfort Single Room, Shared Bathroom (Casato 35) | Exterior
Rinidia Siena Centro

Rinidia Siena Centro

Siena City Centre
8.0 out of 10, Very good, (1)
"The property is in a FANTASTIC location."
United States
Donna
The price is 4.794.748 ₫
5.396.537 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Rinidia Siena Centro
Grand Apartment with Garden | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Front of property
Borgo Antico Residence

Borgo Antico Residence

Certaldo Alto
10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is 2.321.421 ₫
3.410.594 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Borgo Antico Residence
Traditional Apartment | Private kitchen
Duprè Apartment

Duprè Apartment

Siena City Centre
10.0 out of 10, Exceptional, (3)
"Love the space and felt like I was at home . "
United States
Catherine
Duprè Apartment
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio
Affittacamere Le Ginestre

Affittacamere Le Ginestre

San Gimignano City Centre
7.8 out of 10, Good, (6)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
Affittacamere Le Ginestre
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castel San Gimignano Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Beautiful walk to the city center"
Julian 1-night trip
Posted 4 days ago
Hotel Athena

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.

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

With 4 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.