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San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 P7,496
P10,637 total
includes taxes & fees
Oct 16 - Oct 17
AlbergoDiffusoVolterra
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

2. 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 P6,620
P7,493 total
includes taxes & fees
Nov 1 - Nov 2
Tenuta Sant'Ilario
A garden with a stone pathway, wooden benches, and various potted plants.

3. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (87 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is P9,485
P10,785 total
includes taxes & fees
Oct 21 - Oct 22
Antico Borgo il Cardino
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

4. 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 P8,049
P9,064 total
includes taxes & fees
Oct 19 - Oct 20
Tenuta Quadrifoglio
A garden with a round table and wicker chairs under a tree.

5. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (20 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 P3,486
P4,116 total
includes taxes & fees
Oct 22 - Oct 23
Antica Dimora Leones
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

6. 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 P5,764
P6,692 total
includes taxes & fees
Nov 9 - Nov 10
Casa Vacanze Le Case
A building with a stucco exterior, multiple windows, and a tiled roof.

7. 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 P5,652
P6,568 total
includes taxes & fees
Nov 14 - Nov 15
Residence Il Paradiso
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

8. 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 P5,087
P5,595 total
includes taxes & fees
Oct 16 - Oct 17
Beatabb
A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

9. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is P4,656
P5,122 total
includes taxes & fees
Oct 16 - Oct 17
Room Rent Morrona
A kitchen with wooden cabinets, a dining table with chairs, and a hanging light fixture.

10. Toscana Vacanze

Toscana Vacanze
MONTAIONE
The price is P9,292
P16,762 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

11. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is P3,334
P3,879 total
includes taxes & fees
Oct 16 - Oct 17
Camping Boschetto Di Piemma
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

12. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is P9,368
P10,446 total
includes taxes & fees
Oct 28 - Oct 29
Palazzo Pacini
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

13. 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 P4,001
P6,368 total
includes taxes & fees
Oct 16 - Oct 17
Borgo Antico Residence
An open dining area with a table set for two, a red sofa, and a painting on the wall.

14. 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 P11,383
P13,223 total
includes taxes & fees
Oct 16 - Oct 17
La Ripadoro
A view from a window overlooking a rural landscape with fields and a distant mountain range.

15. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 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 P8,556
P9,763 total
includes taxes & fees
Oct 18 - Oct 19
B&B Palazzo Tortoli
A wooden double door with an arch above it, a bench to the left, and a sign with a list of items on the wall.

16. Da Vinci Heart of Tuscany

Da Vinci Heart of Tuscany
Peccioli
Da Vinci Heart of Tuscany
A building with a wooden door, windows with shutters, and flower boxes.

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 P4,791
P5,621 total
includes taxes & fees
Nov 11 - Nov 12
Donna Nobile
A narrow street with stone buildings, a tower, and an archway.

18. 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 P6,611
P7,624 total
includes taxes & fees
Nov 8 - Nov 9
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

19. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 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 P5,738
P8,421 total
includes taxes & fees
Nov 7 - Nov 8
Palazzo al Torrione 2
A poolside area with a lounge chair, a sun hat, and a book.

20. Il Frutteto

Il Frutteto
Casciana Terme Lari
8.6 out of 10, Excellent, (10 reviews)
"-"
Germany
Dr. Björn
The price is P6,053
P7,642 total
includes taxes & fees
Oct 22 - Oct 23
Il Frutteto
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

Mormoraia

Mormoraia

8/10 Good
"Great location close to San Gimignano for day trips Siena, volterra, etc. Beautiful views and very peaceful. Very clean and comfortable hotel, with gorgeous 360 views from rooms. Unfortunately it’s very expensive to use the amenities, so we didn’t use them. The staff are very nice and helpful. The restaurant was OK. The breakfast was good but not great (coffee was great though). We enjoyed their wine."
Breta 4-night trip
Posted 23 hours ago
Mormoraia

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:

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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.