Castel San Gimignano Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Castel San Gimignano vacation rentals

Exterior

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 P10,022
P11,383 total
includes taxes & fees
Jun 3 - Jun 4
Antico Borgo il Cardino
Garden

Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (17 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 P4,371
P5,095 total
includes taxes & fees
Jun 7 - Jun 8
Antica Dimora Leones
Free WiFi

Casa di Alice

Casa di Alice
Barberino Tavarnelle
8.0 out of 10, Very Good, (1 review)
"Very good "
Canada
richard
The price is P6,506
P7,442 total
includes taxes & fees
Jun 25 - Jun 26
Casa di Alice
Exterior

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 P6,900
P7,876 total
includes taxes & fees
Jun 5 - Jun 6
Il Pozzo di Sant'Andrea
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P5,404
P6,874 total
includes taxes & fees
Jun 24 - Jun 25
Tuscasì Aparthotel
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is P11,850
P13,250 total
includes taxes & fees
Jun 25 - Jun 26
Villa Montecastello
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is P7,907
P8,913 total
includes taxes & fees
Jun 14 - Jun 15
Casa di Campagna in Toscana
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is P10,601
P11,805 total
includes taxes & fees
Jun 24 - Jun 25
Palazzo Pacini
Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (42 reviews)
"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
The price is P5,419
P6,390 total
includes taxes & fees
Jun 18 - Jun 19
Villa San Filippo
Terrace/patio

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 P6,798
P7,764 total
includes taxes & fees
Jun 9 - Jun 10
Fullino Nero
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is P5,269
P5,940 total
includes taxes & fees
May 28 - May 29
Chianti Village Morrocco
Seasonal outdoor pool, sun loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is P9,579
P10,752 total
includes taxes & fees
Jun 1 - Jun 2
Residence Arianna
Interior detail

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 P10,833
P12,203 total
includes taxes & fees
Jun 14 - Jun 15
La Coroncina Lodging
Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is P8,593
P9,667 total
includes taxes & fees
Jun 18 - Jun 19
Tenuta Sant'Ilario
Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (244 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is P7,085
P8,080 total
includes taxes & fees
Jun 11 - Jun 12
La Terrazza Sul Campo Rooming House
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is P15,560
P17,259 total
includes taxes & fees
Jun 19 - Jun 20
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 Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"This is a delightful hotel with staff that are extremely friendly and helpful. Although the historic nature of the hotel precluded lifts this did not detract from the stay (one way of saying fit).Huge benefit of having on site parking."
James 3-night trip
Posted 7 hours ago
Hotel Chiusarelli

Find out more about Castel San Gimignano

Search for holiday rentals in Castel San Gimignano on Expedia! You can easily find your home rentals, villas, holiday apartments in Castel San Gimignano using one of the methods below:

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Look no further and take a look at our great range of rental properties in Castel San Gimignano!

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.

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 Castelvecchio Natural Reserve. 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.