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San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 CA $170
CA $242 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $140
CA $159 total
includes taxes & fees
Nov 2 - Nov 3
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, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $192
CA $219 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $183
CA $206 total
includes taxes & fees
Oct 25 - Oct 26
Tenuta Quadrifoglio
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

5. 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 CA $173
CA $194 total
includes taxes & fees
Nov 3 - Nov 4
Palazzo Pacini
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
9.4 out of 10, Exceptional, (13 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 CA $132
CA $153 total
includes taxes & fees
Nov 2 - Nov 3
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, (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 CA $104
CA $115 total
includes taxes & fees
Oct 15 - Oct 16
Residence Il Paradiso
A garden with a round table and wicker chairs under a tree.

8. 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 CA $85
CA $100 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.

9. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is CA $106
CA $117 total
includes taxes & fees
Oct 7 - Oct 8
Room Rent Morrona
A view from a window overlooking a rural landscape with fields and a distant mountain range.

10. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 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 CA $176
CA $201 total
includes taxes & fees
Oct 21 - Oct 22
B&B Palazzo Tortoli
A narrow street with stone buildings, a tower, and an archway.

11. 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 CA $151
CA $174 total
includes taxes & fees
Nov 3 - Nov 4
Materia Rooms San Gimignano
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

12. 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 CA $116
CA $128 total
includes taxes & fees
Oct 11 - Oct 12
Beatabb
An open wooden door leading to an outdoor patio with a table and chairs.

13. 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 CA $150
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
Palazzo al Torrione 2
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 CA $212
CA $249 total
includes taxes & fees
Oct 4 - Oct 5
La Ripadoro
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

15. 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 traveller
The price is CA $69
CA $80 total
includes taxes & fees
Oct 5 - Oct 6
Camping Boschetto Di Piemma
A kitchen with wooden cabinets, a dining table with chairs, and a hanging light fixture.

16. Toscana Vacanze

Toscana Vacanze
MONTAIONE
The price is CA $226
CA $398 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

17. 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 CA $91
CA $145 total
includes taxes & fees
Oct 16 - Oct 17
Borgo Antico Residence
A building with a wooden door, windows with shutters, and flower boxes.

18. 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 CA $105
CA $124 total
includes taxes & fees
Nov 1 - Nov 2
Donna Nobile
A reception desk with the word "SPORTLAND" prominently displayed.

19. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is CA $64
CA $73 total
includes taxes & fees
Oct 4 - Oct 5
Sportland
An arched stone corridor with a hanging lantern, leading to an open area with trees and a gate.

20. Il Castello di San Ruffino

Il Castello di San Ruffino
Casciana Terme Lari
9.2 out of 10, Wonderful, (36 reviews)
"Really cool experience to stay at a castle. Perfect destination for celebrations."
United States
daniel
The price is CA $137
CA $157 total
includes taxes & fees
Oct 24 - Oct 25
Il Castello di San Ruffino
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

Cappuccina Country Resort

Cappuccina Country Resort

8/10 Good
"The hotel is in a beautiful location with stunning views. It’s a 30 minute walk into San Gimignano. A taxi, IF you can get one costs €30 during the day and €60 after 8. It would be great if the hotel offered a shuttle service but it doesn’t. The hotel is part way through a refurbishment, some rooms are still to be upgraded. Our room had a stunning view of the Tuscan countryside. The Spa is only one in the afternoon. Front desk staff were very good, restaurant staff less so. The restaurant is very plain and we were disappointed with breakfast Overall it’s a decent hotel in a wonderful location."
John 3-night trip
Posted 22 hours ago
Cappuccina Country Resort

Find out more about San Cipriano

Everything you need to know about San Cipriano vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the San Cipriano vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Cipriano vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Cipriano vacation rentals we have selected for you start as low as CA $75 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 vacation 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 vacation.

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 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.