Penna Holiday Rentals

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Check prices for these dates

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

Our top choices for Penna holiday rentals

Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is S$217
includes taxes & fees
21 Jun - 22 Jun
Villa Curina Resort
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is S$332
includes taxes & fees
6 Jun - 7 Jun
Castello di Gargonza
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is S$174
includes taxes & fees
17 Jun - 18 Jun
Villa Cassia di Baccano
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is S$273
includes taxes & fees
7 Jun - 8 Jun
Borgo Argenina
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is S$227
includes taxes & fees
18 Jun - 19 Jun
Villa di Sotto
View from room

The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (177 reviews)
"Enjoyed our stay and breakfast was great. "
Canada
Linda
The price is S$121
includes taxes & fees
9 Jun - 10 Jun
The Florence Hills Resort & Wellness
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (319 reviews)
"Beautiful place for family "
Canada
Ismail
The price is S$82
includes taxes & fees
9 Jun - 10 Jun
Hu Norcenni Girasole Village
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is S$147
includes taxes & fees
7 Jun - 8 Jun
iConic Wellness Resort
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
The price is S$219
includes taxes & fees
1 Jul - 2 Jul
L' Eroico
Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is S$159
includes taxes & fees
18 Jun - 19 Jun
DormiVeglia B&B
Front of property

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 S$146
includes taxes & fees
16 Jun - 17 Jun
Villa La Ginestra
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is S$406
includes taxes & fees
23 Jun - 24 Jun
2 Cuori e 1 Yurta Glamping in Toscana
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (74 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is S$163
includes taxes & fees
7 Jun - 8 Jun
Relais Villa Belvedere
Property entrance

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 S$179
includes taxes & fees
6 Jun - 7 Jun
Palazzo Tarlati Residenza d'Epoca
Exterior

B&B da Ronald...a Pian del Papa

B&B da Ronald...a Pian del Papa
Pratovecchio Stia
8.0 out of 10, Very good, (11 reviews)
"Venlig betjening Primitivt Ingen varmt vand Meget koldt værelse"
Denmark
Mikael
The price is S$107
includes taxes & fees
9 Jun - 10 Jun
B&B da Ronald...a Pian del Papa
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (74 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is S$446
includes taxes & fees
16 Jun - 17 Jun
Terre di Baccio
Exterior

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is S$81
includes taxes & fees
7 Jun - 8 Jun
Villa Norcenni Aparthotel
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, pool loungers

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (61 reviews)
"Very friendly staff. Great breakfast! In alla very nice!"
Sweden
martin
The price is S$141
includes taxes & fees
29 Jun - 30 Jun
Villa Il Palagio
View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.6 out of 10, Exceptional, (5 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is S$210
includes taxes & fees
17 Jun - 18 Jun
Casa Vacanze Le Fornaci
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is S$198
includes taxes & fees
16 Jun - 17 Jun
Residenzia del Sogno
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

Borgo Vescine

Borgo Vescine

10/10 Excellent
"We enjoyed our stay immensely. The staff was very accommodating, especially with our two year old. The activities we did (movie night- included; dinner in the olive grove, truffle hunting, & a cooking class- paid) were all lovely experiences. We loved the property grounds."
Christina 4-night trip
Posted 13 hours ago
Borgo Vescine

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.

What are some of the best holiday rentals that Penna has to offer?

Borgo Argiano: This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

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.