Penna Vacation Rentals

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Check prices for these dates

Tonight
Dec 11 - Dec 12
Tomorrow
Dec 12 - Dec 13
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Penna vacation rentals

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is ￥15,897
￥17,761 total
includes taxes & fees
Dec 15 - Dec 16
Relais Villa Belvedere
Exterior
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (148)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire
View from room
The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (175)
"Great stay would recommend "
United Kingdom
Luan
The Florence Hills Resort & Wellness
Property grounds
Typical Tuscan Country House

Typical Tuscan Country House

Typical Tuscan Country House
Pelago
10.0 out of 10, Exceptional, (128)
"Beautiful home and gracious host!"
United States
Levi M.
Typical Tuscan Country House
TV, DVD player, table tennis, books
Typical Tuscan Countryside Cottage near Florence

Typical Tuscan Countryside Cottage near Florence

Typical Tuscan Countryside Cottage near Florence
Bagno a Ripoli, San Bartolomeo A Quarate
10.0 out of 10, Exceptional, (36)
"Magdalena was super helpful letting us know what places there were in the area! The cottage was a great place to stay, and looks better than the pictures! Absolutely an amazing place to stay!"
United States
Dylan K.
Typical Tuscan Countryside Cottage near Florence
1 bedroom, desk, iron/ironing board, travel crib
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Ruffoli
9.8 out of 10, Exceptional, (59)
"This is the most special place I’ve ever been. It’s breathtakingly beautiful. The house itself it’s stunning but the outside terrace and pool area is a dream. I will absolutely come back here again if I get the chance. The host was very helpful, communicative and kind."
United States
Alexandra E.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Exterior
17th century farmhouse with private pool and Wi-Fi and air conditioning

17th century farmhouse with private pool and Wi-Fi and air conditioning

17th century farmhouse with private pool and Wi-Fi and air conditioning
Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveler
17th century farmhouse with private pool and Wi-Fi and air conditioning
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Outdoor pool, a heated pool
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view
Pelago
9.8 out of 10, Exceptional, (106)
"Beautiful, tucked away, yet 20 minutes to train. Really a gem. "
United States
Michael R.
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view
Outdoor pool
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Greve in Chianti
9.0 out of 10, Wonderful, (24)
"Wonderful house with all the facilities you need for self-catering. Although we used it as a base to visit all around the area, we also spent a few days just relaxing in the garden and going to the pool.Well equipped kitchen including a dishwasher and washing machine.Very peacefu, would love to come back one day."
United States
Robert H.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk
Borgo Argiano

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano
Pool
Stunning villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed

Stunning villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed

Stunning villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed
Cavriglia
10.0 out of 10, Exceptional, (13)
"Really great stay here.The villa is absolutely beautiful on the outside and inside.Parking was easy (right in front of property).Location was beautiful and hosts were great."
United States
Mohammed S.
Stunning villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers
Villa Il Palagio

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (60)
"The best place in the region"
United Kingdom
Kamen
Villa Il Palagio
Property grounds
Holiday Villa With Swimming Pool In Arezzo.

Holiday Villa With Swimming Pool In Arezzo.

Holiday Villa With Swimming Pool In Arezzo.
Castel Focognano
10.0 out of 10, Exceptional, (37)
"We had a superb stay which exceeded our expectations. Andrea the host was very kind and welcoming, the house very complete with all requirements and the views fantastic. "
Netherlands
Henk Jan G.
Holiday Villa With Swimming Pool In Arezzo.
Outdoor pool
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.

Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.

Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
Reggello
10.0 out of 10, Exceptional, (48)
"Eduardo’s property was perfect for our family of 5’s stay for 4 days in the Tuscany region. We had access to the entire compound, including olive tree grove, grape vines, and countless other vegetation. The pool was cleanly and a great amenity for our use during our stay. For our stay, it was the ideal setup for space, amenities, and cost.The town is located approximately 45 minutes to Florence, hour to Siena and surrounding vineyards, and 5-10 minutes from the local town. We would recommend...
United States
Drew M.
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
Front of property
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is ￥25,556
￥28,111 total
includes taxes & fees
Dec 11 - Dec 12
Relais Villa Belpoggio - Residenza d'Epoca
Exterior
Borgo Argenina

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
Property grounds
A Panoramic Tuscan Luxury - Villa Maria in Fronzano

A Panoramic Tuscan Luxury - Villa Maria in Fronzano

A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Reggello
10.0 out of 10, Exceptional, (75)
"Walk 5 minutes to a village with grocery store or simply sit by the pool to enjoy the view. This villa has it all! Our family of 10 (adults and kids) spent 2 weeks at Villa Maria and would recommend it for its amenities and location. The host, Tomasso, and chef, Donato, were the ultimate guides and helpers. Take the train into Florence to avoid parking a car. Experience Borroncino Restaurant in Reggello for a gastronomic treat. We would certainly return to this heavenly spot for touring...
United States
Maralin G.
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Front of property
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Spa
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Arezzo Centro Storico
10.0 out of 10, Exceptional, (133)
"Quaint/Historic/Location/Fabulous Weekend of CelebrationBetween Stefano’s hospitality, terrific meals, market in the park and winning the Jousting tournament we could not choose our best memory! Thank you for sharing your chef talent, comfy car and lovely cottage with us. Enjoy your American treats:)"
United States
Katie J.
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 2 days ago
Castello di Fonterutoli Wine Resort

Find out more about Penna

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

  • View our selection of featured holiday rentals in Penna
  • Use the map to find apartments and other holiday homes in the Penna neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Penna while they last

Look no further and take a look at our great range of rental properties in Penna!

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: You might want to consider this vacation home rental near Penna, which 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 a coffee maker. 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. Mulino Ad Acqua 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.