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San Cipriano Vacation Rentals

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Our top choices for San Cipriano vacation rentals

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 $160
CA $230 total
includes taxes & fees
Oct 1 - Oct 2
AlbergoDiffusoVolterra

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 CA $194
CA $202 total
includes taxes & fees
Oct 5 - Oct 6
Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi

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 CA $206
CA $232 total
includes taxes & fees
Sep 27 - Sep 28
Tenuta Quadrifoglio

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 CA $195
CA $223 total
includes taxes & fees
Oct 11 - Oct 12
Antico Borgo il Cardino

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 CA $191
CA $215 total
includes taxes & fees
Oct 11 - Oct 12
Tenuta Sant'Ilario

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 CA $85
CA $100 total
includes taxes & fees
Oct 11 - Oct 12
Antica Dimora Leones

7. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is CA $102
CA $113 total
includes taxes & fees
Sep 27 - Sep 28
Room Rent Morrona

8. Medieval tranquillity in lush, Tuscan nature

Medieval tranquillity in lush, Tuscan nature
Montecatini Val di Cecina
The price is CA $241
CA $278 total
includes taxes & fees
Oct 3 - Oct 4
Medieval tranquillity in lush, Tuscan nature

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 CA $181
CA $207 total
includes taxes & fees
Sep 20 - Sep 21
Casa Vacanze Le Case

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 traveller
The price is CA $64
CA $75 total
includes taxes & fees
Sep 16 - Sep 17
Camping Boschetto Di Piemma

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 CA $91
CA $100 total
includes taxes & fees
Oct 2 - Oct 3
Affittacamere e Ristorante Ariete

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 CA $105
CA $115 total
includes taxes & fees
Sep 20 - Sep 21
Residence Il Paradiso

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 CA $192
CA $219 total
includes taxes & fees
Oct 15 - Oct 16
B&B Palazzo Tortoli

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 CA $113
CA $124 total
includes taxes & fees
Oct 11 - Oct 12
Beatabb

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 CA $138
CA $200 total
includes taxes & fees
Sep 27 - Sep 28
Palazzo al Torrione 2

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 CA $113
CA $169 total
includes taxes & fees
Sep 15 - Sep 16
La Casina of Via Cresci, 14

17. 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 CA $214
CA $239 total
includes taxes & fees
Oct 15 - Oct 16
Palazzo Pacini

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 CA $225
CA $264 total
includes taxes & fees
Oct 8 - Oct 9
La Ripadoro

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 CA $92
CA $146 total
includes taxes & fees
Sep 27 - Sep 28
Borgo Antico Residence

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 CA $121
CA $142 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

Find out more about San Cipriano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.