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San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for San Cipriano vacation 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 ￥18,128
￥26,027 total
includes taxes & fees
Sep 29 - Sep 30
AlbergoDiffusoVolterra
A swimming pool with lounge chairs, surrounded by a low wall, under a sunset sky.

2. 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, (2 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 ￥21,612
￥22,507 total
includes taxes & fees
Oct 5 - Oct 6
Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

3. 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 ￥22,945
￥25,777 total
includes taxes & fees
Sep 28 - Sep 29
Tenuta Quadrifoglio
A garden with a stone pathway, wooden benches, and various potted plants.

4. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ￥22,233
￥25,352 total
includes taxes & fees
Oct 13 - Oct 14
Antico Borgo il Cardino
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

5. 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 ￥17,128
￥19,379 total
includes taxes & fees
Oct 18 - Oct 19
Tenuta Sant'Ilario
A garden with a round table and wicker chairs under a tree.

6. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (18 reviews)
"What a truly special place to stay in Tuscany. Zamira was a wonderful and kind hostess, and we couldn’t have asked for more. Breathtaking views from the hotel, delicious breakfast, and some great restaurants in walking distance. Would 100% go back and would highly recommend it to fellow travellers"
United Kingdom
Thomas
The price is ￥9,038
￥10,659 total
includes taxes & fees
Oct 18 - Oct 19
Antica Dimora Leones
A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

7. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is ￥11,864
￥13,051 total
includes taxes & fees
Sep 18 - Sep 19
Room Rent Morrona
A terrace with a view of the landscape, outdoor seating, and decorative lighting.

8. Medieval tranquillity in lush, Tuscan nature

Medieval tranquillity in lush, Tuscan nature
Montecatini Val di Cecina
The price is ￥26,851
￥31,326 total
includes taxes & fees
Oct 3 - Oct 4
Medieval tranquillity in lush, Tuscan nature
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

9. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is ￥19,494
￥22,338 total
includes taxes & fees
Oct 4 - Oct 5
Casa Vacanze Le Case
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

10. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is ￥7,730
￥9,040 total
includes taxes & fees
Sep 22 - Sep 23
Camping Boschetto Di Piemma
A courtyard with outdoor seating, a brick building, and a tree.

11. Affittacamere e Ristorante Ariete

Affittacamere e Ristorante Ariete
Ponsacco
8.8 out of 10, Excellent, (3 reviews)
"This place is a bit further out from Pisa, but we still had a really nice stay and made the most of it. It’s great value for money, which was a big plus. The hotel itself is a little old-fashioned, but honestly, the staff more than made up for it—they were super friendly and welcoming the whole time. The restaurant was also a highlight, with really tasty food that we enjoyed a lot. It’s a good spot if you’ve got a car and want to explore the nearby villages and surrounding area."
United Kingdom
Martina
The price is ￥10,122
￥11,134 total
includes taxes & fees
Sep 18 - Sep 19
Affittacamere e Ristorante Ariete
A building with a stucco exterior, multiple windows, and a tiled roof.

12. 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 ￥11,675
￥12,843 total
includes taxes & fees
Sep 29 - Sep 30
Residence Il Paradiso
A view from a window overlooking a rural landscape with fields and a distant mountain range.

13. 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 ￥21,821
￥24,899 total
includes taxes & fees
Oct 18 - Oct 19
B&B Palazzo Tortoli
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

14. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 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 ￥12,323
￥13,556 total
includes taxes & fees
Oct 11 - Oct 12
Beatabb
An open wooden door leading to an outdoor patio with a table and chairs.

15. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is ￥16,805
￥23,856 total
includes taxes & fees
Sep 23 - Sep 24
Palazzo al Torrione 2
A narrow street with buildings on either side, featuring stone walls and metal gates.

16. La Casina of Via Cresci, 14

La Casina of Via Cresci, 14
Montaione
10.0 out of 10, Exceptional, (4 reviews)
"Cute villa- exactly as described. "
United States
Jo P.
The price is ￥12,531
￥18,796 total
includes taxes & fees
Oct 12 - Oct 13
La Casina of Via Cresci, 14
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

17. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (101 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ￥23,893
￥26,640 total
includes taxes & fees
Oct 1 - Oct 2
Palazzo Pacini
An open dining area with a table set for two, a red sofa, and a painting on the wall.

18. La Ripadoro

La Ripadoro
Chianni
10.0 out of 10, Exceptional, (1 review)
"Amazing place Amazing view Amazing food Amazing people. Highly recommended."
Canada
Maya
The price is ￥25,046
￥29,341 total
includes taxes & fees
Sep 29 - Sep 30
La Ripadoro
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

19. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is ￥10,193
￥16,224 total
includes taxes & fees
Oct 11 - Oct 12
Borgo Antico Residence
A building with a wooden door, windows with shutters, and flower boxes.

20. 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 ￥13,506
￥15,753 total
includes taxes & fees
Oct 4 - Oct 5
Donna Nobile
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 Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"If you are driving around in Tuscany and need a place to stay, look no further! The place is beautiful, clean, friendly staff and feels like a 5 star hotel without the price. location was central to all the wineries and Tuscany sites. Breakfast was fantastic. Awesome place!"
George 1-night trip
Posted 2 days ago
Hotel Casolare Le Terre Rosse

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
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  • 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?

San Francesco Country Resort: Visitors like this San Cipriano vacation home rental. It offers a private beach, a furnished patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Amenities like 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 yard.

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.