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San Cipriano Holiday Rentals

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Our top choices for San Cipriano holiday rentals

1. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Amazing property. Very beautiful "
Canada
Charles
The price is NZ$298
includes taxes & fees
22 Aug - 23 Aug
AlbergoDiffusoVolterra

2. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is NZ$331
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino

3. Villa Tosca

Villa Tosca
Peccioli
The price is NZ$2,309
includes taxes & fees
23 Aug - 24 Aug
Villa Tosca

4. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is NZ$238
includes taxes & fees
28 Aug - 29 Aug
Casa Vacanze Le Case

5. 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 NZ$132
includes taxes & fees
12 Aug - 13 Aug
Antica Dimora Leones

6. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NZ$261
includes taxes & fees
21 Aug - 22 Aug
Palazzo al Torrione 2

7. AWESHOMEITALY - VILLA SAN MARTINO

AWESHOMEITALY - VILLA SAN MARTINO
La Fornace
The price is NZ$2,472
includes taxes & fees
4 Sept - 5 Sept
AWESHOMEITALY - VILLA SAN MARTINO

8. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is NZ$273
includes taxes & fees
6 Sept - 7 Sept
Tenuta Sant'Ilario

9. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is NZ$370
includes taxes & fees
27 Aug - 28 Aug
B&B Palazzo Tortoli

10. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NZ$215
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini

11. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is NZ$167
includes taxes & fees
12 Aug - 13 Aug
Donna Nobile

12. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is NZ$127
includes taxes & fees
13 Aug - 14 Aug
Room Rent Morrona

13. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is NZ$88
includes taxes & fees
6 Sept - 7 Sept
Sportland

14. Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (26 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$218
includes taxes & fees
30 Aug - 31 Aug
Residence Il Paradiso

15. La Ripadoro

La Ripadoro
Chianni
The price is NZ$586
includes taxes & fees
19 Aug - 20 Aug
La Ripadoro

16. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (46 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is NZ$226
includes taxes & fees
1 Sept - 2 Sept
Villa San Filippo

17. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is NZ$213
includes taxes & fees
18 Aug - 19 Aug
Materia Rooms San Gimignano

18. B&B Il Moscondoro

B&B Il Moscondoro
Montopoli in Val d'Arno
8.0 out of 10, Very good, (8 reviews)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is NZ$168
includes taxes & fees
15 Aug - 16 Aug
B&B Il Moscondoro

19. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (88 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is NZ$97
includes taxes & fees
7 Sept - 8 Sept
Camping Boschetto Di Piemma

20. Beatabb

Beatabb
Guardistallo
9.2 out of 10, Wonderful, (15 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
The price is NZ$186
includes taxes & fees
3 Sept - 4 Sept
Beatabb
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

Find out more about San Cipriano

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Cipriano holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Cipriano. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Cipriano. Seeing all the best attractions is bound to make you fall in love with San Cipriano. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Cipriano short-term rentals, that won’t be hard to do.

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. Kitchen amenities include a fridge, a stovetop and a microwave. 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 Peccioli Prehistoric Park, 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.