Default HTG hotel image

San Cipriano Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for San Cipriano vacation rentals

1. Volaterrae Deluxe Loft with Garden

Volaterrae Deluxe Loft with Garden
Volterra
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, spacious apartment that has been newly renovated. It’s in a perfect location that was great for our needs. We would stay there again."
United States
Eleni O.
The price is CA $176
CA $281 total
includes taxes & fees
Aug 6 - Aug 7
Volaterrae Deluxe Loft with Garden

2. Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is CA $233
CA $266 total
includes taxes & fees
Aug 21 - Aug 22
Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

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 $223
CA $251 total
includes taxes & fees
Aug 8 - Aug 9
Tenuta Quadrifoglio

4. 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 CA $102
CA $119 total
includes taxes & fees
Aug 8 - Aug 9
Antica Dimora Leones

5. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is CA $93
CA $103 total
includes taxes & fees
Aug 4 - Aug 5
Room Rent Morrona

6. San Lorenzo by Interhome

San Lorenzo by Interhome
Gambassi Terme
9.4 out of 10, Exceptional, (10 reviews)
"Piękne widoki, prawdziwa toskańska wieś. Cisza, spokój i cudowne otoczenie. Komfortowy domek. Bardzo miły i pomocny gospodarz. Te wakacje na długo zostaną w mej pamięci jako wyjątkowo udane."
United States
Dorota
The price is CA $236
CA $241 total
includes taxes & fees
Aug 21 - Aug 22
San Lorenzo by Interhome

7. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is CA $141
CA $164 total
includes taxes & fees
Aug 6 - Aug 7
Materia Rooms San Gimignano

8. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (86 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is CA $76
CA $89 total
includes taxes & fees
Aug 23 - Aug 24
Camping Boschetto Di Piemma

9. 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 CA $322
CA $363 total
includes taxes & fees
Aug 4 - Aug 5
Antico Borgo il Cardino

10. 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 CA $179
CA $205 total
includes taxes & fees
Aug 16 - Aug 17
Casa Vacanze Le Case

11. 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 $257
CA $287 total
includes taxes & fees
Aug 4 - Aug 5
Tenuta Sant'Ilario

12. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $151
CA $215 total
includes taxes & fees
Aug 8 - Aug 9
Palazzo al Torrione 2

13. 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 $95
CA $105 total
includes taxes & fees
Aug 14 - Aug 15
Affittacamere e Ristorante Ariete

14. 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 $122
CA $142 total
includes taxes & fees
Aug 3 - Aug 4
Donna Nobile

15. 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 $160
CA $179 total
includes taxes & fees
Sep 2 - Sep 3
Palazzo Pacini

16. Da Vinci Heart of Tuscany

Da Vinci Heart of Tuscany
Peccioli
The price is CA $142
CA $237 total
includes taxes & fees
Aug 3 - Aug 4
Da Vinci Heart of Tuscany

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 $110
CA $166 total
includes taxes & fees
Aug 8 - Aug 9
Borgo Antico Residence

18. 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 $184
CA $202 total
includes taxes & fees
Aug 31 - Sep 1
Residence Il Paradiso

19. Il Castello di San Ruffino

Il Castello di San Ruffino
Casciana Terme Lari
9.2 out of 10, Wonderful, (33 reviews)
"Really cool experience to stay at a castle. Perfect destination for celebrations."
United States
daniel
The price is CA $149
CA $171 total
includes taxes & fees
Aug 26 - Aug 27
Il Castello di San Ruffino

20. Casa Magnolia Enjoy unrivaled view and breathtaking sunsets - CIELO

Casa Magnolia Enjoy unrivaled view and breathtaking sunsets - CIELO
Terricciola
9.2 out of 10, Wonderful, (9 reviews)
"It really was a wonderful stay in Stefania and Maurizio's accommodation. The pictures reflected the accommodation very well and the sunset was fantastic every evening! The village of Terricciola is a great starting point for excursions and also offers a nice selection of restaurants and wineries. If we go to Tuscany again, we will definitely consider the flat again!"
Germany
Jan Z.
Casa Magnolia Enjoy unrivaled view and breathtaking sunsets - CIELO
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.
Save an average of 15% on thousands of hotels when you're signed in

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. Kitchen amenities include a fridge, a stovetop, and a microwave. 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.