Castel San Gimignano Holiday Rentals

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Check prices for these dates

Tonight
17 Dec - 18 Dec
Tomorrow
18 Dec - 19 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Castel San Gimignano holiday rentals

Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is S$101
includes taxes & fees
19 Dec - 20 Dec
ApartHotel Anghel
View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$114
includes taxes & fees
20 Dec - 21 Dec
Tuscasì Aparthotel
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Private kitchen
Regis Condo

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
View from room
Residenza d'Epoca Palazzo Borghesi

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 S$235
includes taxes & fees
6 Jan - 7 Jan, 2026
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

Camping Siena Colleverde
3.0 star property
Scacciapensieri
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Exterior detail
La Casa di Ines

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is S$130
includes taxes & fees
19 Dec - 20 Dec
La Casa di Ines
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is S$130
includes taxes & fees
19 Dec - 20 Dec
La Coroncina Lodging
Seasonal outdoor pool, pool umbrellas, pool loungers
Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo
Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveller
Castello Del Nero - Podere San Filippo
Living area
Casa Ciseri

Casa Ciseri

Casa Ciseri
Siena City Centre
9.8 out of 10, Exceptional, (9)
"Very nice stay!"
United States
Danielle
The price is S$380
includes taxes & fees
18 Dec - 19 Dec
Casa Ciseri
Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

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

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 S$336
includes taxes & fees
22 Dec - 23 Dec
Palazzo Lenzi
Outdoor pool, pool umbrellas, pool loungers
Riserva di Fizzano Residence

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (24)
"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
Riserva di Fizzano Residence
Seasonal outdoor pool, pool umbrellas, pool loungers
Villa San Filippo

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (40)
"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."
United Kingdom
Andrew
Villa San Filippo
Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.0 out of 10, Very good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is S$176
includes taxes & fees
21 Dec - 22 Dec
Casa Vacanze Squarcialupi
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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"The best in Siena."
David 1-night trip
Posted 4 days ago
Hotel Certosa Di Maggiano

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.

What are some of the best holiday rentals that Castel San Gimignano has to offer?

Agriturismo La Ferrozzola: This holiday home rental outside Castel San Gimignano offers a terrace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Val di Merse. In the wider area, you’ll find Sovestro in Poggio Winery and Historical Torture Museum.

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.