San Cipriano Vacation Rentals

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Check prices for these dates

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

Vacation Rentals in San Cipriano

Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun 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
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 ￥14,532
￥21,405 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo al Torrione 2
Comfort Room | Premium bedding, free WiFi
Room Rent Morrona

Room Rent Morrona

Terricciola
9.0 out of 10, Wonderful, (6)
"Ottima struttura "
Italy
Marzia
Room Rent Morrona
Property grounds
2bed, 1bath Garden apt in Chianti!

2bed, 1bath Garden apt in Chianti!

Frazione Mura, Montaione
10.0 out of 10, Exceptional, (3)
"We had a wonderful time staying at the house. The location is beautiful and peaceful, surrounded by nature and the house itself is charming and well cared for. The swimming pool and the tennis court were fantastic and made our stay even more enjoyable. It was the perfect place to relax and enjoy the Tuscan atmosphere. We truly enjoyed our stay and would love to return one day"
Germany
Cayit A.
The price is ￥12,645
￥32,153 total
includes taxes & fees
Dec 7 - Dec 8
2bed, 1bath Garden apt in Chianti!
Fridge, oven, stovetop, dishwasher
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveler
The price is ￥14,276
￥20,507 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
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
Down comforters, Select Comfort beds, in-room safe
Donna Nobile

Donna Nobile

San Gimignano City Centre
8.2 out of 10, Very Good, (157)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is ￥12,316
￥14,451 total
includes taxes & fees
Dec 9 - Dec 10
Donna Nobile
Netflix, streaming services
Two Bedroom Apartment

Two Bedroom Apartment

San Gimignano City Centre
9.8 out of 10, Exceptional, (11)
"Very well set up apartment and location was perfect. Parking is a bit of a challenge but if you don’t mind walking you will be ok. "
Canada
Bev P.
The price is ￥17,702
￥30,347 total
includes taxes & fees
Dec 16 - Dec 17
Two Bedroom Apartment
Exterior
Sportland

Sportland

Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Pool
2-BR 1 bath abode in the Chianti hills!

2-BR 1 bath abode in the Chianti hills!

Mura, Montaione
8.0 out of 10, Very Good, (1)
"Check in Vorgang schwierig, da Gastgeber vergessen hat, dass wir kommen. Dann aber hat alles gut geklappt.Die Wohnung ist sehr renovierungsbedürftig, mein Mann hat erstmal die Klospülung repariert. Sonst hat sie ihren Charme und ist gut ausgestattet Gewürzen und anderen LebensmittelnToll gelegen mit Pool und Tennisplatz"
Germany
Anke G.
The price is ￥10,838
￥30,166 total
includes taxes & fees
Dec 8 - Dec 9
2-BR 1 bath abode in the Chianti hills!
Daily self-serve breakfast (EUR 6 per person)
Beatabb

Beatabb

Guardistallo
9.0 out of 10, Wonderful, (7)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
Beatabb
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 ￥18,565
￥21,324 total
includes taxes & fees
Dec 8 - Dec 9
B&B Palazzo Tortoli
1 bedroom, in-room safe, travel crib, WiFi
Colle di Val D'elsa - Siena - Apt Green - E

Colle di Val D'elsa - Siena - Apt Green - E

Colle di Val d'Elsa
10.0 out of 10, Exceptional, (1)
"Tutto bellissimo. Dal check in on line semplice e funzionale, l'apertura con il codice permette di arrivare quando si vuole. Alloggio esattamente come nelle foto, pulitissimo e dotato di tutto quello che serve anche per la preparazione dei cibi. Bagno particolare trasparente, pulitissimo e con doccia doppi. Vasca idromassaggio davanti al letto ... la chicca"
Italy
Stefano S.
The price is ￥14,270
￥26,914 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Colle di Val D'elsa - Siena - Apt Green - E
Exterior
2-bedroom apartment in classical Tuscan style

2-bedroom apartment in classical Tuscan style

Pomarance
The price is ￥16,095
￥22,959 total
includes taxes & fees
Dec 7 - Dec 8
2-bedroom apartment in classical Tuscan style
Interior
Le Torri San Gimignano Apartments

Le Torri San Gimignano Apartments

San Gimignano City Centre
8.4 out of 10, Very Good, (5)
"Loved this apartment. Felt like we were locals. Walked to everything. Outstanding communication with property manager. She was very helpful and accommodating. She was able to help us navigate how to return to our train station as transportation from here can be tricky if not planned in advance."
United States
Antonio M.
The price is ￥18,064
￥32,515 total
includes taxes & fees
Dec 7 - Dec 8
Le Torri San Gimignano Apartments
Interior
Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa
10.0 out of 10, Exceptional, (2)
"Super clean and a comfortable bed. Everything essential for making meals at home was provided. The host was very attentive and available by text. Housekeeping did an excellent job!"
United States
ALLAN
The price is ￥13,006
￥25,650 total
includes taxes & fees
Dec 8 - Dec 9
Colle di Val d'Elsa - Siena - Apt Blue - C
Microwave, stovetop, dishwasher
Le Torri2 SanGimignanoApartments

Le Torri2 SanGimignanoApartments

San Gimignano City Centre
10.0 out of 10, Exceptional, (1)
"Muy bonito y acogedor "
Mexico
ROCIO
The price is ￥22,399
￥34,140 total
includes taxes & fees
Dec 8 - Dec 9
Le Torri2 SanGimignanoApartments
Fridge, microwave, oven, stovetop
Two-room apartament in heart of tuscany

Two-room apartament in heart of tuscany

Montopoli
10.0 out of 10, Exceptional, (1)
"Very friendly host, nice apartment. All the kitchen tools to make meals there. The neighborhood was friendly but it was noisy a bit at night due to the dogs. "
Canada
Annie-Ève
The price is ￥9,639
￥13,794 total
includes taxes & fees
Dec 7 - Dec 8
Two-room apartament in heart of tuscany
1 bedroom, WiFi, bed sheets
THE BEST VIEW San Gimignano

THE BEST VIEW San Gimignano

SAN GIMIGNANO
8.8 out of 10, Excellent, (3)
"It was a lovely apartment and the host is absolutely fabulous and easy to talk/chat with and responsive and they went above and beyound when I left my wallet behind on the day I flew out. When I stayed it was extremely hot(big European heat wave) and it was difficult to get cooled down at night but I think this was unusual time but be careful if you are sensitive to the heat at night."
United States
Eileen B.
The price is ￥12,103
￥22,038 total
includes taxes & fees
Dec 12 - Dec 13
THE BEST VIEW San Gimignano
Property grounds
VACATION HOME IN THE TUSCAN COUNTRYSIDE - PODERE SAN GIUSTO - VOLTERRA

VACATION HOME IN THE TUSCAN COUNTRYSIDE - PODERE SAN GIUSTO - VOLTERRA

Volterra
The price is ￥18,064
￥21,315 total
includes taxes & fees
Dec 7 - Dec 8
VACATION HOME IN THE TUSCAN COUNTRYSIDE - PODERE SAN GIUSTO - VOLTERRA
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 San Cipriano Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 5 days ago
Hotel Borgo di Cortefreda Relais

Find out more about San Cipriano

Search for holiday rentals in San Cipriano on Expedia! You can easily find your home rentals, villas, holiday apartments in San Cipriano 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 San Cipriano!

Frequently asked questions

Can I find a vacation rental in San Cipriano?

Yes, we have vacation rentals near the most popular attractions in San Cipriano, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in San Cipriano?

Antico Podere San Francesco Hotel: Visitors like this San Cipriano vacation home rental. It offers a balcony, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the private yard in this rental home to help you unwind.

What can I see and do in San Cipriano?

Explore the area and family-friendly sights such as Pasta Martelli, or get out into nature at a spot like Casciana Thermal Baths. Roman Theatre and Cathedral of Volterra are a couple of places you'll find in the larger area.

What are vacation rentals like in San Cipriano?

Vacation rentals are privately owned accommodations you can book for a couple days or more in San Cipriano. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family gatherings.