San Cipriano Holiday 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for San Cipriano holiday rentals

7.2 out of 10, Good, (15)
"Cabins are great, everything is clean and beds where fine. Swimming pool is a little too warm and the pool surface is basicly stones that gave the kids open wounds. The restaurant didnt sell anything but chips. "
Iceland
Anonymous traveller
The price is AU$111
includes taxes & fees
29 Jan - 30 Jan 2026
Toscana Biovillage - Cottage con Vasca Idromassaggio solo su Richiesta

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is AU$137
includes taxes & fees
6 Jan - 7 Jan 2026
La Casa di Ines

Holiday Home in Rosignano Marittimo

Antico Podere San Francesco Hotel
9.6 out of 10, Exceptional, (38)
"Very nice property, lovely breakfast and friendly staff!"
United Kingdom
David
Antico Podere San Francesco Hotel

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
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

Aparthotel in Guardistallo

Beatabb
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

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Townhouse in Terricciola

Room Rent Morrona
9.0 out of 10, Wonderful, (6)
"Ottima struttura "
Italy
Marzia
Room Rent Morrona

Townhouse in Montopoli in Val d'Arno

B&B Il Moscondoro
8.0 out of 10, Very good, (8)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is AU$158
includes taxes & fees
30 Dec - 31 Dec
B&B Il Moscondoro

Holiday Home in San Gimignano

Casa Vacanze Le Case
9.0 out of 10, Wonderful, (8)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AU$183
includes taxes & fees
11 Jan - 12 Jan 2026
Casa Vacanze Le Case

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AU$208
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2

Residence in Guardistallo

Residence Il Paradiso
3.0 star property
8.4 out of 10, Very good, (25)
"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"
Germany
Jason
The price is AU$153
includes taxes & fees
30 Dec - 31 Dec
Residence Il Paradiso
10.0 out of 10, Exceptional, (1)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is AU$2,843
includes taxes & fees
6 Jan - 7 Jan 2026
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveller
The price is AU$214
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Apartment in Certaldo Alto

Borgo Antico Residence
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 AU$195
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo Antico Residence

Villa in Casciana Terme

Villa Cattleya
10.0 out of 10, Exceptional, (1)
"Tout était impeccable. "
France
Stéphane S.
The price is AU$224
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Cattleya

Aparthotel in Casciana Terme Lari

Il Frutteto
8.6 out of 10, Excellent, (9)
"-"
Germany
Dr. Björn
The price is AU$261
includes taxes & fees
4 Jan - 5 Jan 2026
Il Frutteto

Apartment in Colle di Val d'Elsa

Colle di Val d'Elsa - Siena - Apt Pink - B
10.0 out of 10, Exceptional, (2)
"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."
United States
Tamara C.
The price is AU$241
includes taxes & fees
6 Jan - 7 Jan 2026
Colle di Val d'Elsa - Siena - Apt Pink - B

Apartment in Colle di Val d'Elsa

Colle di Val D'elsa - Siena - Apt Green - E
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 AU$246
includes taxes & fees
8 Jan - 9 Jan 2026
Colle di Val D'elsa - Siena - Apt Green - E

Apartment in Colle di Val d'Elsa

Colle di Val d'Elsa - Siena - Apt Blue - C
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 AU$252
includes taxes & fees
6 Jan - 7 Jan 2026
Colle di Val d'Elsa - Siena - Apt Blue - C
10.0 out of 10, Exceptional, (1)
"Alloggio immerso nel verde nel centro della Toscana, equidistante da Firenze, Pisa e Siena, a due passi da San Gimignano, situato a 500 metri sul l.m. Bilocale completo di tutto. Siamo stati accolti da una Sig.ra gentilissima e molto professionale. Che pretendere di più? Io e mia moglie abbiamo trascorso una settimana di fine settembre fantastica"
Italy
giovanni a.
Second floor apartment approx 50 sqm 1 bedroom 1 bathroom with shower 4 beds
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Cipriano Hotel Reviews

Find out more about San Cipriano

Everything you need to know about San Cipriano holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Cipriano holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Cipriano holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

San Cipriano holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Cipriano. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Cipriano holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Cipriano holiday rentals we have selected for you start as low as AU$137 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Cipriano rentals

At Expedia, we put the best San Cipriano holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Cipriano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Cipriano holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Cipriano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in San Cipriano?

Yes, there are holiday rentals close to the most popular sights in San Cipriano, or you can select a more secluded option if you're looking for a relaxing stay.

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

Antico Podere San Francesco Hotel: This holiday home rental outside of San Cipriano offers a balcony, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of private gardens 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 wider area.

What are holiday rentals like in San Cipriano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Cipriano. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to 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 a family getaway.