A city with historic towers and a vineyard.

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Castel San Gimignano holiday rentals

Exterior

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 4.936.306 ₫
5.579.522 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Antico Borgo il Cardino
Terrace/patio

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 2.596.760 ₫
2.916.270 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Palazzo Pacini
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
The price is 2.808.401 ₫
3.986.751 ₫ total
includes taxes & fees
8 Aug - 9 Aug
Palazzo al Torrione 2
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

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 3.798.100 ₫
4.327.494 ₫ total
includes taxes & fees
30 Jul - 31 Jul
B&B Palazzo Tortoli
Outdoor pool

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 3.190.843 ₫
3.659.512 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Casa Vacanze Le Case
Porch

Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
The price is 2.175.864 ₫
2.542.946 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Donna Nobile
Superior Mobile Home | Terrace/patio

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 1.468.776 ₫
1.705.405 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Camping Boschetto Di Piemma
La Torre Grossa | In-room safe, desk, laptop workspace, free WiFi

Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is 2.620.219 ₫
3.031.894 ₫ total
includes taxes & fees
1 Aug - 2 Aug
Materia Rooms San Gimignano
Garden view

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 2.895.694 ₫
3.364.765 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Villa San Filippo
Villa, Air conditioning, Courtyard View | Exterior

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 4.954.256 ₫
5.539.433 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Villa Montecastello
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 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is 3.237.156 ₫
3.710.456 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Affittacamere Le Ginestre
Garden

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 4.133.932 ₫
4.637.136 ₫ total
includes taxes & fees
1 Aug - 2 Aug
Tenuta Quadrifoglio
Food court

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 4.405.959 ₫
6.970.662 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Borgo Il Poggiaccio
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

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 4.754.084 ₫
5.319.244 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Tenuta Sant'Ilario
Aerial view

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 6.731.327 ₫
7.464.294 ₫ total
includes taxes & fees
19 Aug - 20 Aug
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

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Très belle hôtel bien situé pour visiter les villages des environs si vous aimez voir les paysages toscans"
Martin 2-night trip
Posted less than an hour ago
Hotel Casolare Le Terre Rosse

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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 3 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 Alta Val d'Elsa River Park. In the wider area, you’ll find Sovestro in Poggio Winery and Casa e Torre Campatelli.

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.