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Cennina Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Cennina vacation rentals

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

1. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is P10,585
P11,643 total
includes taxes & fees
Oct 21 - Oct 22
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

2. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is P10,389
P11,711 total
includes taxes & fees
Oct 29 - Oct 30
Villa Curina Resort
An arched stone bridge with a white building on the right, featuring a balcony with plants.

3. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is P7,271
P7,998 total
includes taxes & fees
Oct 20 - Oct 21
Locanda Antico Borgo
A stone building with a yellow sign reading "b&b erioico".

4. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is P8,153
P9,535 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A cozy living room with a stone wall, a wine rack, and two sofas.

5. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is P7,274
P8,356 total
includes taxes & fees
Oct 20 - Oct 21
Villa Cassia di Baccano
A neatly made bed with a tray of breakfast items, a window with curtains, and a mirror on the wall.

6. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is P6,969
P7,949 total
includes taxes & fees
Nov 8 - Nov 9
DormiVeglia B&B
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

7. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is P5,849
P6,717 total
includes taxes & fees
Oct 20 - Oct 21
Villa Fontis Rapolano
A stone building with a garden in front.

8. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is P11,183
P12,867 total
includes taxes & fees
Oct 26 - Oct 27
Borgo Argenina
A stone building with a sloped roof, a small porch, and a gravel driveway.

9. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.2 out of 10, Wonderful, (33 reviews)
"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...
United Kingdom
Kevin
The price is P6,597
P7,540 total
includes taxes & fees
Oct 20 - Oct 21
Podere La Chiusella
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

10. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is P15,282
P17,093 total
includes taxes & fees
Oct 20 - Oct 21
Castello di Gargonza
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

11. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"Very nice hotel with friendly stad"
Denmark
Lisette
The price is P7,586
P8,557 total
includes taxes & fees
Oct 20 - Oct 21
Casa Vacanze Le Fornaci
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

12. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is P10,231
P11,254 total
includes taxes & fees
Oct 20 - Oct 21
Relais Villa Belpoggio - Residenza d'Epoca
Property entrance

13. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
The price is P10,295
P11,325 total
includes taxes & fees
Oct 20 - Oct 21
Palazzo Tarlati Residenza d'Epoca
A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

14. La Murata

La Murata
Rapolano Terme
9.2 out of 10, Wonderful, (13 reviews)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is P8,699
P9,853 total
includes taxes & fees
Oct 20 - Oct 21
La Murata
Pool

15. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is P4,691
P5,585 total
includes taxes & fees
Nov 16 - Nov 17
iConic Wellness Resort
An arched stone gateway leading to a pathway lined with potted plants and lights.

16. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is P6,312
P9,350 total
includes taxes & fees
Oct 22 - Oct 23
Castello di Modanella
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

17. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is P5,212
P6,087 total
includes taxes & fees
Oct 20 - Oct 21
RESIDENCE LECCIO
A rustic kitchen with wooden cabinets, a hanging pot rack, and a built-in air conditioner.

18. 2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is P15,011
P16,936 total
includes taxes & fees
Oct 22 - Oct 23
2 Cuori e 1 Yurta Glamping in Toscana
A hotel room with a bed, a bedside table, a mirror, and a ceiling with wooden beams.

19. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is P4,182
P5,839 total
includes taxes & fees
Oct 20 - Oct 21
Limehome Arezzo Duomo
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 Cennina Hotel Reviews

Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"Great location and very helpful staff"
Edward 2-night trip
Posted 10 hours ago
Il Chiostro del Carmine

Find out more about Cennina

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

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Frequently asked questions

Can I find a vacation rental in Cennina?

Yes, you can find vacation rentals close to the most popular sights in Cennina, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Cennina has to offer?

Borgo Argiano: This vacation home rental near Cennina is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library.

What’s there to see and do in Cennina?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Terme Antica Querciolaia. In the larger area, you’ll find Villa a Sesta Polo Club and Castle of Brolio.

What’s a vacation rental in Cennina like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Cennina. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for small groups.