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Check prices for these dates

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

Our top choices for Penna holiday rentals

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

1. 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 4.197.282 ₫
4.617.011 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Relais Villa Belpoggio - Residenza d'Epoca
A cozy living room with a stone wall, a wine rack, and two sofas.

2. 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 2.984.200 ₫
3.282.620 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Villa Cassia di Baccano
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

3. 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 3.112.174 ₫
3.510.560 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Casa Vacanze Le Fornaci
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

4. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is 2.713.022 ₫
3.027.960 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Relais Villa Belvedere
A stone building with a yellow sign reading "b&b erioico".

5. 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 3.344.812 ₫
3.911.588 ₫ total
includes taxes & fees
9 Nov - 10 Nov
L' Eroico
An arched stone bridge with a white building on the right, featuring a balcony with plants.

6. 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 2.982.880 ₫
3.281.168 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Locanda Antico Borgo
A stone building with arched windows and a gravel driveway.

7. Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
The price is 2.850.894 ₫
3.223.094 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Villa La Ginestra
A villa with a swimming pool, outdoor seating, and a tennis court.

8. 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 4.262.034 ₫
4.804.444 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Villa Curina Resort
A hotel room with a bed, a bedside table, a mirror, and a ceiling with wooden beams.

9. 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 1.930.466 ₫
2.632.602 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Limehome Arezzo Duomo
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 6.269.328 ₫
7.012.409 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Castello di Gargonza
Pool

11. 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 1.924.448 ₫
2.291.114 ₫ total
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

12. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is 4.186.538 ₫
4.750.376 ₫ total
includes taxes & fees
21 Oct - 22 Oct
LE BOTTI FIORENTINE
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

13. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is 4.342.387 ₫
4.776.626 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A modern living room with a television, a sliding glass door leading to a patio with outdoor furniture.

14. The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (180 reviews)
"Enjoyed our stay and breakfast was great. "
Canada
Linda
The price is 1.722.176 ₫
2.010.757 ₫ total
includes taxes & fees
4 Nov - 5 Nov
The Florence Hills Resort & Wellness
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 Penna Hotel Reviews

Hotel Villa Cesi

Hotel Villa Cesi

10/10 Excellent
"Rooms are very clean and staff are very friendly and super helpful and above all they are caring and very accommodating especially with our elderly less abled parents for which we are very grateful. Property is in a beautiful setting. Restaurant staff also very helpful. Thank you very much to all who hosted us at Villa Cesi."
Anshi 2-night trip
Posted 2 days ago
Hotel Villa Cesi

Frequently asked questions

Are there holiday rentals in Penna?

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

How many holiday rentals are there in Penna?

Choose from 3 Expedia holiday rentals in Penna for a memorable holiday.

What can I see and do in Penna?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Piazza Guido Monaco. San Pietro a Gropina and Croce del Pratomagno are a couple of places you'll find in the wider area.

What are holiday rentals like in Penna?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Penna. Holiday rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.