San Cipriano Vacation Rentals

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
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

Balcony
Palazzo al Torrione 2

Townhouse in 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 NT$2,940
NT$4,330 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo al Torrione 2
Exterior detail
B&B Palazzo Tortoli

Townhouse in 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 NT$3,847
NT$4,414 total
includes taxes & fees
Jan 4 - 2026/1/5
B&B Palazzo Tortoli
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers
Tenuta Sant'Ilario

Townhouse in 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
Exterior
Sportland

Townhouse in Colle di Val d'Elsa

7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio
Affittacamere Le Ginestre

Townhouse in 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

Townhouse in 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 NT$2,491
NT$2,923 total
includes taxes & fees
Dec 5 - Dec 6
Donna Nobile
Property entrance
Palazzo Pacini

Residence in Colle di Val d'Elsa

9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
Palazzo Pacini
Daily self-serve breakfast (EUR 6 per person)
Beatabb

Aparthotel in 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
Comfort Room | Premium bedding, free WiFi
Room Rent Morrona

Townhouse in Terricciola

9.0 out of 10, Wonderful, (6)
"Ottima struttura "
Italy
Marzia
Room Rent Morrona
Front of property
Borgo Antico Residence

Apartment in 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 NT$2,771
NT$4,071 total
includes taxes & fees
Jan 2 - 2026/1/3
Borgo Antico 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.
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 San Cipriano Hotel Reviews

Hotel Toscana Ambassador

Hotel Toscana Ambassador

10/10 Excellent
"We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. "
Cevat A 9-night trip
Posted 8 days ago
Hotel Toscana Ambassador

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:

  • View our selection of featured holiday rentals in San Cipriano
  • Use the map to find apartments and other holiday homes in the San Cipriano neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in San Cipriano while they last

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.