San Cipriano Holiday Rentals from AU$72: Search Short-Term Rentals

Q: What are some of the best holiday rentals that San Cipriano has to offer?

San Francesco Country Resort : This holiday home rental outside of San Cipriano offers a private beach, a furnished patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Amenities such as 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 garden.

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Our top choices for San Cipriano holiday rentals

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

1. Tenuta Sant'Ilario

Gambassi Terme

Sergio

includes taxes & fees

5 Nov - 6 Nov

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

2. AlbergoDiffusoVolterra

Volterra

Mia

includes taxes & fees

6 Nov - 7 Nov

A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

3. Tenuta Quadrifoglio

Gambassi Terme

Geraldine

includes taxes & fees

2 Nov - 3 Nov

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

4. Casa Vacanze Le Case

San Gimignano

Andrew

includes taxes & fees

10 Nov - 11 Nov

A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

5. Room Rent Morrona

Terricciola

Marzia

includes taxes & fees

2 Nov - 3 Nov

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

6. Borgo Antico Residence

Certaldo Alto

jane

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with a stone wall, wooden staircase, and a breakfast bar with fruit and beverages.

7. Beatabb

Guardistallo

Joanne

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a large bed, a wooden wardrobe, a desk with a lamp, and a chair.

8. Volaterrae Deluxe Loft with Garden

Volterra

Eleni O.

includes taxes & fees

2 Nov - 3 Nov

A building with a stucco exterior, multiple windows, and a tiled roof.

9. Residence Il Paradiso

Guardistallo

Jason

includes taxes & fees

21 Nov - 22 Nov

A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

10. Sportland

Colle di Val d'Elsa

Giorgio

includes taxes & fees

2 Nov - 3 Nov

A building with a wooden door, windows with shutters, and flower boxes.

11. Donna Nobile

San Gimignano City Centre

Treena

includes taxes & fees

2 Nov - 3 Nov

A courtyard with stone buildings, a grassy area, and a brick wall.

12. Toscana Vacanze

MONTAIONE

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with lounge chairs, surrounded by a low wall, under a sunset sky.

13. Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi

Volterra

Michael B.

includes taxes & fees

15 Nov - 16 Nov

An open wooden door leading to an outdoor patio with a table and chairs.

14. Palazzo al Torrione 2

San Gimignano City Centre

Angel

includes taxes & fees

2 Nov - 3 Nov

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

15. Palazzo Pacini

Colle di Val d'Elsa

John

includes taxes & fees

2 Dec - 3 Dec

A courtyard with outdoor seating, a brick building, and a tree.

16. Affittacamere e Ristorante Ariete

Ponsacco

"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."

Martina

includes taxes & fees

8 Nov - 9 Nov

A room with exposed wooden beams, a wooden door, and a framed picture on the wall.

17. 2bed, 1bath Garden apt in Chianti!

Frazione Mura, Montaione

Cayit A.

includes taxes & fees

3 Nov - 4 Nov

A terrace with a view of the landscape, outdoor seating, and decorative lighting.

18. Medieval tranquillity in lush, Tuscan nature

Montecatini Val di Cecina

includes taxes & fees

5 Nov - 6 Nov

A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

19. Villa Le Polle di Meletro

Rivalto

includes taxes & fees

2 Nov - 3 Nov

A historic stone building with a prominent tower, arched windows, and a tiled roof.

20. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

includes taxes & fees

3 Nov - 4 Nov

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Top San Cipriano Hotel Reviews

San Francesco Country Resort

8/10 Good

"Breakfast was excellent, friendly staff, clean facilities. bed was uncomfortable as it was a murphy bed and no night stands to put anything. nice little kitchen but layout was awkward with the tv to the side of the bed."

Castelfalfi

10/10 Excellent

"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay was ultra responsive, during our stay they were always present. You want attention to detail, Castelfalfi has it covered. Drinks are carefully made and delivered. Turn down service straightened the room, put little clothes under anything we had on the bathroom sink or room table, a new bookmark was left next to my book on the nightstand, cords were always wrapped and made to look tidy, I could go on and on. The food in the various restaurants was amazing. The little meat and cheese shop made a tremendous& fresh sandwich sliced up right in front of us on fresh baked bread. The view of sunset from the back deck had many guests out watching for good reason. The spa pool was great and the gym was pretty big. The breakfast buffet had everything you could want. Want fresh honey? There was a station with a honeycomb taken from their property…it drips fresh honey into a tray that empties into a bowl for you. The wine tasting was fun and delicious and worth it. Everything is on site and you will not want to leave the property during your stay or at the end of your trip. Castelfalfi- I hope and pray I return some day, thank you!!"

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Absolutely lovely hotel. Best one we stayed at in Italy - in retrospect, we wish we booked to stay here a second night. The location is quiet and isolated so stars are visible at night, plenty of parking, and breakfast is worth the 20 EURS, best breakfast options we had during our stay. Highly recommend, 10/10."

Relais Santa Chiara Hotel by Double Hospitality

10/10 Excellent

"The biggest mistake we made... was leaving. What a wonderful place to stay and enjoy the Tuscan countryside. The proximity to Sam Gimignano was perfect. Short stroll of 7 minutes and you are there. Room was clean and comfortable. Great water pressure in the shower with plenty of hot water. Loved the charm of this hotel. Met by Gaia... so hospitable and helpful. She walked us out to show us where parking had been set aside for us as asked (I received welcome emails ahead of my stay and inquired about parking. All was neatly arranged.) We enjoyed dinner in the bar area twice. All meals were wonderful. But the breakfast spread was just delightful. So many choices of fresh food. Delicious!! Thank you for a wonderful stay. Molto bene!!! Gratzie mille, Gaia!!"

Find out more about San Cipriano

Everything you need to know about San Cipriano holiday rentals

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

San Cipriano holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Cipriano holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Cipriano holiday rentals we have selected for you start as low as AU$72 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Cipriano rentals

At Expedia, we put the best San Cipriano holiday 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 holiday.

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 holiday rental in San Cipriano?

Yes, there are holiday rentals close to the most popular sights in San Cipriano, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Cipriano has to offer?

San Francesco Country Resort: This holiday home rental outside of San Cipriano offers a private beach, a furnished patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Amenities such as 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 garden.

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 wider area.

What are holiday rentals like in San Cipriano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Cipriano. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family getaway.

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Check prices for these dates

Our top choices for San Cipriano holiday rentals

1. Tenuta Sant'Ilario

2. AlbergoDiffusoVolterra

3. Tenuta Quadrifoglio

4. Casa Vacanze Le Case

5. Room Rent Morrona

6. Borgo Antico Residence

7. Beatabb

8. Volaterrae Deluxe Loft with Garden

9. Residence Il Paradiso

10. Sportland

11. Donna Nobile

12. Toscana Vacanze

13. Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi

14. Palazzo al Torrione 2

15. Palazzo Pacini

16. Affittacamere e Ristorante Ariete

17. 2bed, 1bath Garden apt in Chianti!

18. Medieval tranquillity in lush, Tuscan nature

19. Villa Le Polle di Meletro

20. Materia Rooms San Gimignano

Find holiday rentals that suit your style

Top San Cipriano Hotel Reviews

San Francesco Country Resort

La Cisterna

Castelfalfi

Tenuta Sovestro - Agriturismo e Winery

Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo San Luigi

Hotel Casolare Le Terre Rosse

Relais Santa Chiara Hotel by Double Hospitality

Villa Sabolini

Find out more about San Cipriano

Frequently asked questions

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