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San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$146 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
AlbergoDiffusoVolterra
A swimming pool with lounge chairs, surrounded by a low wall, under a sunset sky.

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.
$138 nightly
The price is $143
Oct 5 - Oct 6
Total with taxes and fees
Apartment 'Casa Vacanze Podere San Giusto' with Private Terrace, Private Garden and Wi-Fi
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

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
$130 nightly
The price is $147
Oct 19 - Oct 20
Total with taxes and fees
Tenuta Quadrifoglio
A garden with a stone pathway, wooden benches, and various potted plants.

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
$140 nightly
The price is $160
Oct 15 - Oct 16
Total with taxes and fees
Antico Borgo il Cardino
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

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
$101 nightly
The price is $114
Oct 26 - Oct 27
Total with taxes and fees
Tenuta Sant'Ilario
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)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
$123 nightly
The price is $141
Oct 4 - Oct 5
Total with taxes and fees
Casa Vacanze Le Case
A garden with a round table and wicker chairs under a tree.

7. 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
$53 nightly
The price is $63
Oct 11 - Oct 12
Total with taxes and fees
Antica Dimora Leones
A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

8. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
$68 nightly
The price is $75
Sep 27 - Sep 28
Total with taxes and fees
Room Rent Morrona
A terrace with a view of the landscape, outdoor seating, and decorative lighting.

9. Medieval tranquillity in lush, Tuscan nature

Medieval tranquillity in lush, Tuscan nature
Montecatini Val di Cecina
$179 nightly
The price is $183
Oct 3 - Oct 4
Total with taxes and fees
Medieval tranquillity in lush, Tuscan nature
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

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 traveler
$47 nightly
The price is $55
Oct 4 - Oct 5
Total with taxes and fees
Camping Boschetto Di Piemma
A building with a stucco exterior, multiple windows, and a tiled roof.

11. 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
$74 nightly
The price is $82
Oct 4 - Oct 5
Total with taxes and fees
Residence Il Paradiso
A spacious living room with a sofa, chairs, and a coffee table. There is a kitchen area visible through an archway.

12. Casa del Pozzo, a smart home in Lajatico with air conditioning and garden

Casa del Pozzo, a smart home in Lajatico with air conditioning and garden
Lajatico
$354 nightly
The price is $359
Oct 9 - Oct 10
Total with taxes and fees
Casa del Pozzo, a smart home in Lajatico with air conditioning and garden
A view from a window overlooking a rural landscape with fields and a distant mountain range.

13. 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
$130 nightly
The price is $149
Oct 18 - Oct 19
Total with taxes and fees
B&B Palazzo Tortoli
A courtyard with outdoor seating, a brick building, and a tree.

14. 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
$59 nightly
The price is $65
Oct 17 - Oct 18
Total with taxes and fees
Affittacamere e Ristorante Ariete
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

15. 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
$82 nightly
The price is $91
Oct 11 - Oct 12
Total with taxes and fees
Beatabb
An open wooden door leading to an outdoor patio with a table and chairs.

16. 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
$133 nightly
The price is $152
Oct 27 - Oct 28
Total with taxes and fees
Palazzo al Torrione 2
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
$91 nightly
The price is $103
Oct 11 - Oct 12
Total with taxes and fees
Borgo Antico Residence
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

18. Simona delightful studio apartment with pool view

Simona delightful studio apartment with pool view
Castel San Gimignano
9.8 out of 10, Exceptional, (7 reviews)
"Perfect stay"
Germany
Marcel H.
Simona delightful studio apartment with pool view
Two people seated on a wooden chair with a plaid cushion, a table with a charcuterie board between them, and a potted plant to the right.

19. ViaGiotto A welcoming and well-kept apartment in Tuscany,

ViaGiotto A welcoming and well-kept apartment in Tuscany,
Certaldo
9.4 out of 10, Exceptional, (3 reviews)
"This is truly a welcoming apartment in a small town easily accessible to other sites. Clean, up to date with many little thoughtful touches. Our hostess was very friendly and helpful. This is our fifth Vrbo in Italy and one of the best. "
United States
Teresa S.
$97 nightly
The price is $101
Oct 7 - Oct 8
Total with taxes and fees
ViaGiotto A welcoming and well-kept apartment in Tuscany,
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

20. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
$193 nightly
The price is $212
Sep 29 - Sep 30
Total with taxes and fees
Villa Le Polle di Meletro
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

Villa Sabolini

Villa Sabolini

8/10 Good
"Beautiful 14th century villa in the Tuscan hills with very pretty pool and restaurant areas, and very helpful and friendly staff. The food was hearty and enjoyable, but not the highest standard, even compared to restaurants in the area. It's in a great location for exploring Florence, Chianti region and Siena. The room we used (superior garden view) was good, very interesting features due to the age of the property, with a stunning view. However, it was not very cosy for spending time in and the A/C struggled as well. Overall we were very happy with our choice and had a great stay!"
Morgan 10-night trip
Posted 1 day ago
Villa Sabolini

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit San Cipriano in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $55 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.