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San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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 P7,323
P10,507 total
includes taxes & fees
Sep 3 - Sep 4
AlbergoDiffusoVolterra
A garden with a stone pathway, wooden benches, and various potted plants.

2. 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 P11,180
P12,659 total
includes taxes & fees
Sep 3 - Sep 4
Antico Borgo il Cardino
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
The price is P9,246
P10,387 total
includes taxes & fees
Sep 7 - Sep 8
Tenuta Quadrifoglio
A garden with a round table and wicker chairs under a tree.

4. 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 P3,791
P4,459 total
includes taxes & fees
Sep 3 - Sep 4
Antica Dimora Leones
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, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is P9,617
P10,723 total
includes taxes & fees
Sep 25 - Sep 26
Palazzo Pacini
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

6. 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 P9,282
P10,426 total
includes taxes & fees
Sep 29 - Sep 30
Tenuta Sant'Ilario
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

7. 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 P8,098
P9,269 total
includes taxes & fees
Sep 17 - Sep 18
Casa Vacanze Le Case
A view from a window overlooking a rural landscape with fields and a distant mountain range.

8. 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 P8,970
P10,228 total
includes taxes & fees
Sep 1 - Sep 2
B&B Palazzo Tortoli
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

9. 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 P4,107
P6,538 total
includes taxes & fees
Sep 26 - Sep 27
Borgo Antico Residence
An open dining area with a table set for two, a red sofa, and a painting on the wall.

10. 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 P11,803
P13,705 total
includes taxes & fees
Sep 10 - Sep 11
La Ripadoro
A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

11. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
The price is P4,780
P5,258 total
includes taxes & fees
Sep 1 - Sep 2
Room Rent Morrona
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, (18 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 P5,222
P5,744 total
includes taxes & fees
Sep 20 - Sep 21
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, (112 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 P6,771
P9,612 total
includes taxes & fees
Sep 3 - Sep 4
Palazzo al Torrione 2
A building with a stucco exterior, multiple windows, and a tiled roof.

14. 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 P5,716
P6,288 total
includes taxes & fees
Sep 6 - Sep 7
Residence Il Paradiso
A building with a wooden door, windows with shutters, and flower boxes.

15. 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 P5,180
P6,059 total
includes taxes & fees
Sep 1 - Sep 2
Donna Nobile
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

16. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is P11,990
P16,302 total
includes taxes & fees
Sep 26 - Sep 27
Villa Le Polle di Meletro
A pool area with clear water, lounge chairs, and umbrellas.

17. Hu Montescudaio Village

Hu Montescudaio Village
3.0 star property
Montescudaio
9.6 out of 10, Exceptional, (28 reviews)
"We had an amazing time and the place was very genuine, had a great pool and nice restaurant."
Sweden
Anders
The price is P6,303
P7,222 total
includes taxes & fees
Sep 1 - Sep 2
Hu Montescudaio Village
A stone building with a large tree in front, outdoor seating with tables and chairs, and a view of the surrounding landscape.

18. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is P13,540
P15,254 total
includes taxes & fees
Sep 4 - Sep 5
Borgo al Cerro
A narrow street with stone buildings, a tower, and an archway.

19. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is P6,964
P8,021 total
includes taxes & fees
Sep 1 - Sep 2
Materia Rooms San Gimignano
A courtyard with outdoor seating, a brick building, and a tree.

20. 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 P4,249
P4,674 total
includes taxes & fees
Sep 4 - Sep 5
Affittacamere e Ristorante Ariete
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

LHP Certaldo Resort

LHP Certaldo Resort

10/10 Excellent
"Hotel was excellent in every way! The staff was amazing attending to our every need. Pool was a big plus in the hot summer weather! Breakfast buffet was also amazing. The location was a little disappointing being a little farther from the old Certaldo than expected. Also disappointing was the size of the shower in our room, make sure to get a bathroom with a good sized shower. Definitely would return without hesitation!"
Hermano 4-night trip
Posted 14 hours ago
LHP Certaldo Resort

Find out more about San Cipriano

Search for holiday rentals in San Cipriano on Expedia! You can easily find your home rentals, villas, holiday apartments in San Cipriano using one of the methods below:

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Look no further and take a look at our great range of rental properties in San Cipriano!

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.