San Cipriano Holiday Rentals

  • 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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for San Cipriano holiday rentals

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

1. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Lovely stay at a little gem in Volterra. Enrico the owner has created a great concept with different apartments around the city and the restaurant is serving delicious local plant based food. Don’t miss the cheesecake ❤️"
Sweden
Mia
The price is NZ$330
includes taxes & fees
22 Nov - 23 Nov
AlbergoDiffusoVolterra
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

2. 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 NZ$257
includes taxes & fees
27 Nov - 28 Nov
Tenuta Quadrifoglio
A bedroom with a large bed, a wooden wardrobe, a desk with a lamp, and a chair.

3. Volaterrae Deluxe Loft with Garden

Volaterrae Deluxe Loft with Garden
Volterra
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, spacious apartment that has been newly renovated. It’s in a perfect location that was great for our needs. We would stay there again."
United States
Eleni O.
The price is NZ$248
includes taxes & fees
15 Nov - 16 Nov
Volaterrae Deluxe Loft with Garden
A stone building with a pool and outdoor seating, surrounded by greenery and a view of distant mountains.

4. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is NZ$179
includes taxes & fees
15 Nov - 16 Nov
Casa Vacanze Le Case
A dining area with tables set for meals, a chandelier, and a view of the outdoors.

5. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NZ$234
includes taxes & fees
3 Dec - 4 Dec
Palazzo Pacini
A building entrance with a wooden door, a window with a metal grille, and a sign on the wall.

6. Babaia, Cozy Apartment in the Historic Center of Volterra

Babaia, Cozy Apartment in the Historic Center of Volterra
Volterra
10.0 out of 10, Exceptional, (1 review)
"Michele is a great host! He did not hover but responded in a timely manner if we had a question. The apartment was clean, comfortable and located within walking distance of everything Volterra has to offer. We would absolutely stay there again!"
United States
Beverly B.
The price is NZ$297
includes taxes & fees
15 Nov - 16 Nov
Babaia, Cozy Apartment in the Historic Center of Volterra
A staircase with metal railings leading to a building entrance.

7. Apartment 'Cielo' with Shared Garden, Wi-Fi and Air Conditioning

Apartment 'Cielo' with Shared Garden, Wi-Fi and Air Conditioning
Volterra
10.0 out of 10, Exceptional, (1 review)
"Pros: Die Gastgeber waren immer sehr freundlich und zuvorkommend, man konnte sich gut mit ihnen unterhalten und sie waren immer erreichbar bei Fragen und Problemen. Wir waren zu zehnt da, drei Erwachsene und sieben Kinder/ Kleinkinder und es war genug Platz für alle da. Volterra ist 25 Autominuten entfernt, die nächsten Strände und Pisa ungefähr eine Stunde. Zum zur Ruhe kommen und Abschalten ist dieser Ort ideal. Für die Benutzung des Pools sind Badekappen gewünscht. Diese am besten schon...
Germany
Anonymous traveller
The price is NZ$446
includes taxes & fees
15 Nov - 16 Nov
Apartment 'Cielo' with Shared Garden, Wi-Fi and Air Conditioning
A rural property with a paved driveway, a small building with a tiled roof, and a well-maintained garden with various plants and flowers.

8. Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (27 reviews)
"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 NZ$209
includes taxes & fees
17 Nov - 18 Nov
Residence Il Paradiso
A covered patio with a table and chairs, surrounded by potted plants and a barbecue grill.

9. Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi

Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi
Volterra
10.0 out of 10, Exceptional, (3 reviews)
"Beautifully decorated flat with everything you need (we didn't see a toaster but we didn't need one).Very tidy. Very good beds. Cristina and her family were very friendly and helped with everything.Beautiful region, beautiful garden, house, everything perfect.We got a lot of regional products as gifts and they were really tasty (and healthy)."
Germany
Michael B.
The price is NZ$229
includes taxes & fees
15 Nov - 16 Nov
Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi
A bathroom with a white sink, a large mirror, and a towel rack with pink towels.

10. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"Beautiful B&B! Clean, comfortable room & wonderful breakfast "
United States
Joanne
The price is NZ$140
includes taxes & fees
15 Dec - 16 Dec
Beatabb
A narrow alleyway with brick walls, wooden barrels, and potted plants.

11. Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.

Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.
San Gimignano City Centre
9.8 out of 10, Exceptional, (44 reviews)
"P. Buonaccorsi is a unique property that is centrally located in San Gimignano. It is well maintained and restored and a very beautiful residence. Senora and Bianca were perfect hosts. The town was perfectly located in Tuscany and within easy day-trips to Florence, Siena, and Massa Marittima."
United States
Glenn
The price is NZ$279
includes taxes & fees
15 Nov - 16 Nov
Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.
A room with exposed wooden beams, a sloped ceiling, and a brick wall.

12. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
Room Rent Morrona
A spacious living room with a sofa, two armchairs, a coffee table, and a dining area in the background.

13. Casa del Pozzo, a smart home in Lajatico with air conditioning and a garden

Casa del Pozzo, a smart home in Lajatico with air conditioning and a garden
Lajatico
The price is NZ$501
includes taxes & fees
15 Nov - 16 Nov
Casa del Pozzo, a smart home in Lajatico with air conditioning and a garden
A view from a window overlooking a rural landscape with fields and a distant mountain range.

14. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is NZ$192
includes taxes & fees
1 Dec - 2 Dec
B&B Palazzo Tortoli
An open doorway leading to a patio with a table and chairs, a potted plant, and a view of a building across the lawn.

15. La Ripadoro

La Ripadoro
Chianni
10.0 out of 10, Exceptional, (2 reviews)
"Amazing place Amazing view Amazing food Amazing people. Highly recommended."
Canada
Maya
The price is NZ$244
includes taxes & fees
15 Nov - 16 Nov
La Ripadoro
A terrace with a view of the landscape, outdoor seating, and decorative lighting.

16. Medieval tranquillity in lush, Tuscan nature

Medieval tranquillity in lush, Tuscan nature
Montecatini Val di Cecina
The price is NZ$297
includes taxes & fees
15 Nov - 16 Nov
Medieval tranquillity in lush, Tuscan nature
A view from a window overlooking a forested area with a clear sky.

17. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is NZ$160
includes taxes & fees
8 Dec - 9 Dec
Donna Nobile
An open wooden door leading to an outdoor patio with a table and chairs.

18. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Very friendly host 🙌 and great location"
Denmark
Klaus
The price is NZ$244
includes taxes & fees
17 Nov - 18 Nov
Palazzo al Torrione 2
An outdoor brick barbecue area with a wooden bench nearby.

19. Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!

Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!
Frazione Mura, Montaione
10.0 out of 10, Exceptional, (3 reviews)
"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.
Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!
A narrow street with stone buildings, wooden doors, and a brick pathway.

20. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is NZ$216
includes taxes & fees
26 Nov - 27 Nov
Materia Rooms San Gimignano
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

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Top San Cipriano Hotel Reviews

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.
Albergo Etruria

Albergo Etruria

Albergo Etruria
Volterra

10/10 Excellent

The hotel is in an excellent position so close to restaurants and museum . It has a great rooftop. The breakfast was excellent and the service was great. The owner was very accomodating and friendly. He even wheeled our heaving suitcases to the car. Would recommend this hotel and will be back
Australia
Alan
Reviewed September 4, 2025
Albergo Etruria

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 favorite 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 depends 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 NZ$98 per night. Entering your travel dates in the search wizard you might find 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?

San Francesco Country Resort: This holiday home rental outside of San Cipriano offers a private beach, a furnished patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Amenities such as an electric kettle and free parking are also available for your convenience. Kick off your shoes and enjoy yourself with a terrace and a private garden.

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.