San Cipriano Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for San Cipriano vacation rentals

Exterior

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 P4,534
P4,988 total
includes taxes & fees
Jun 2 - Jun 3
Residence Il Paradiso
Outdoor dining

Affittacamere e Ristorante Ariete

Affittacamere e Ristorante Ariete
Ponsacco
9.0 out of 10, Wonderful, (2 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 P4,701
P5,172 total
includes taxes & fees
Jun 7 - Jun 8
Affittacamere e Ristorante Ariete
Seasonal outdoor pool

Antico Podere San Francesco Hotel

Antico Podere San Francesco Hotel
Rosignano Marittimo
9.6 out of 10, Exceptional, (45 reviews)
"Very nice property, lovely breakfast and friendly staff!"
United Kingdom
David
The price is P8,979
P10,020 total
includes taxes & fees
Jun 12 - Jun 13
Antico Podere San Francesco Hotel
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is P9,784
P15,862 total
includes taxes & fees
Jun 14 - Jun 15
Borgo Il Poggiaccio
View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (63 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 P9,429
P10,731 total
includes taxes & fees
Jun 3 - Jun 4
B&B Palazzo Tortoli
Room service - dining

B&B Il Moscondoro

B&B Il Moscondoro
Montopoli in Val d'Arno
8.0 out of 10, Very Good, (8 reviews)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is P6,203
P6,823 total
includes taxes & fees
Jun 2 - Jun 3
B&B Il Moscondoro
Restaurant

Hotiday Relais Costa degli Etruschi

Hotiday Relais Costa degli Etruschi
Rosignano Marittimo
10.0 out of 10, Exceptional, (2 reviews)
"De passage dans la région, je pensais faire une étape sans saveur, mais l'accueil qui m'a été réservé et la qualité de l'hébergement m'ont véritablement enchanté. La rénovation de l'ancien bâtiment en petites suites et l'aménagement intelligent de l'établissement est réussi et très séduisant. Si vous êtes dans la région ne cherchez pas plus loin, vous serez, comme moi, enchanté. Je recommande fortement"
France
Bernard
The price is P6,042
P6,790 total
includes taxes & fees
Jun 4 - Jun 5
Hotiday Relais Costa degli Etruschi
Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (42 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
The price is P4,516
P5,399 total
includes taxes & fees
Jun 3 - Jun 4
Villa San Filippo
Daily self-serve breakfast for a fee

Beatabb

Beatabb
Guardistallo
9.2 out of 10, Wonderful, (9 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 P5,265
P5,792 total
includes taxes & fees
Jun 7 - Jun 8
Beatabb
Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is P8,622
P9,699 total
includes taxes & fees
Jun 18 - Jun 19
Tenuta Sant'Ilario
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is P11,312
P12,803 total
includes taxes & fees
Jun 7 - Jun 8
Antico Borgo il Cardino
Garden

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 P4,241
P4,953 total
includes taxes & fees
Jun 2 - Jun 3
Antica Dimora Leones
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is P10,640
P11,848 total
includes taxes & fees
Jun 9 - Jun 10
Palazzo Pacini
Bathroom

Room Rent Morrona

Room Rent Morrona
Terricciola
9.0 out of 10, Wonderful, (6 reviews)
"Ottima struttura "
Italy
Marzia
The price is P4,760
P5,236 total
includes taxes & fees
Jun 2 - Jun 3
Room Rent Morrona
Exterior

Il Castello di San Ruffino

Il Castello di San Ruffino
Casciana Terme Lari
9.2 out of 10, Wonderful, (30 reviews)
"Really cool experience to stay at a castle. Perfect destination for celebrations."
United States
daniel
The price is P6,231
P7,142 total
includes taxes & fees
Jun 8 - Jun 9
Il Castello di San Ruffino
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is P4,231
P4,798 total
includes taxes & fees
Jun 29 - Jun 30
Sportland
Balcony

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 P6,742
P9,571 total
includes taxes & fees
Jun 2 - Jun 3
Palazzo al Torrione 2
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is P7,133
P8,206 total
includes taxes & fees
Jun 29 - Jun 30
Casa Vacanze Le Case
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is P10,872
P12,174 total
includes taxes & fees
Jun 2 - Jun 3
Antico Borgo Poggiarello
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is P11,894
P13,299 total
includes taxes & fees
Jun 2 - Jun 3
Villa Montecastello
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

Hotel Sovestro

Hotel Sovestro

10/10 Excellent
"Breakfast was great, but dinner must be reserved in advance."
Igor 1-night trip
Posted 14 hours ago
Hotel Sovestro

Find out more about San Cipriano

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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?

Antico Podere San Francesco Hotel: Visitors like this San Cipriano vacation home rental. It offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the private yard in this rental home to help you unwind.

What can I see and do in San Cipriano?

Explore the area and family-friendly sights such as Peccioli Prehistoric Park, 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.