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Penna Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Penna vacation 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, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is AED 579
AED 637 total
includes taxes & fees
18 Nov - 19 Nov
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 AED 346
AED 381 total
includes taxes & fees
15 Nov - 16 Nov
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 AED 377
AED 427 total
includes taxes & fees
22 Nov - 23 Nov
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 AED 376
AED 420 total
includes taxes & fees
3 Dec - 4 Dec
Relais Villa Belvedere
A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

5. A cozy little house

A cozy little house
Loro Ciuffenna
The price is AED 320
AED 332 total
includes taxes & fees
1 Dec - 2 Dec
A cozy little house
A stone building with a yellow sign reading "b&b erioico".

6. 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 AED 466
AED 545 total
includes taxes & fees
27 Nov - 28 Nov
L' Eroico
An arched stone bridge with a white building on the right, featuring a balcony with plants.

7. 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 AED 377
AED 414 total
includes taxes & fees
13 Dec - 14 Dec
Locanda Antico Borgo
Pool

8. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (45 reviews)
"It was wonderful!"
United States
Wade
The price is AED 277
AED 329 total
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
A modern living room with a television, a sliding glass door leading to a patio with outdoor furniture.

9. 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 AED 240
AED 280 total
includes taxes & fees
30 Nov - 1 Dec
The Florence Hills Resort & Wellness
A stone building with arched windows and a gravel driveway.

10. 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 AED 386
AED 436 total
includes taxes & fees
8 Dec - 9 Dec
Villa La Ginestra
A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

11. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is AED 573
AED 650 total
includes taxes & fees
15 Nov - 16 Nov
LE BOTTI FIORENTINE
A poolside setting with two glasses of red drink, a tray with chips and olives, and a white umbrella.

12. Apartment in the Tuscan countryside with swimming pool.

Apartment in the Tuscan countryside with swimming pool.
Reggello FI
10.0 out of 10, Exceptional, (1 review)
Apartment in the Tuscan countryside with swimming pool.
A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

13. Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi
Figline Valdarno
The price is AED 241
AED 461 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi
A rustic patio with a wooden table and chairs, a stone wall, and a view of greenery outside.

14. Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool

Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool
Pian di Scò
The price is AED 426
AED 471 total
includes taxes & fees
20 Nov - 21 Nov
Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool
A view from a window overlooking a rural landscape with a tall tree and distant hills.

15. A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi

A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
Cavriglia
A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

16. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is AED 327
AED 614 total
includes taxes & fees
24 Nov - 25 Nov
LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
A clear blue pool with lounge chairs and umbrellas, surrounded by trees and a hill in the background.

17. Relais Santa Margherita

Relais Santa Margherita
Capolona
8.0 out of 10, Very good, (6 reviews)
"Man entspannt gerne am Pool und der Bar."
Germany
Anonymous traveler
Relais Santa Margherita
A spa area with a stone-walled arch, a hot tub, and a small window.

18. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (31 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is AED 422
AED 481 total
includes taxes & fees
1 Dec - 2 Dec
DormiVeglia B&B
A narrow street with buildings on either side, stone walls, and a clear blue sky.

19. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is AED 377
AED 684 total
includes taxes & fees
25 Nov - 26 Nov
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Property entrance

20. 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 AED 589
AED 648 total
includes taxes & fees
13 Dec - 14 Dec
Palazzo Tarlati Residenza d'Epoca
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

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

10/10 Excellent
"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"
Kelly 2-night trip
Posted 6 days ago
Il Borro - Relais & Châteaux

Frequently asked questions

Are there vacation rentals in Penna?

Yes, we offer vacation rentals near the most popular local attractions in Penna, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Penna?

Borgo Argiano: Visitors like this Penna vacation home rental. It 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.

How many vacation rentals are there in Penna?

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

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 larger area.

What are vacation rentals like in Penna?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Penna. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.