Holiday houses in Penna

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Top-rated holiday rentals in Penna

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Guest favourite

Home in Poggio San Marco

4.97 out of 5 average rating, 276 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Top Guest favourite

Farm stay in Ruscello

4.99 out of 5 average rating, 422 reviews

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €10 per person (€6 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

Top Guest favourite

Home in Panzano

4.98 out of 5 average rating, 442 reviews

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Top Guest favourite

Guesthouse in Macciano

4.96 out of 5 average rating, 165 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Superhost

Condo in Castelfranco di Sopra

4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

Top Guest favourite

Holiday home in Terranuova Bracciolini

5 out of 5 average rating, 29 reviews

"Podere Carpognane" Tuscany Holiday House

Villetta con 3 camere matrimoniali (6 posti letto), 2 bagni con box doccia, cucina accessoriata, sala da pranzo, veranda esterna. Circondata da un ampio giardino con olivi e vigneto. Piscina privata in muratura, 10x5mt, con lettini ed ombrelloni. Due posti auto coperti. Gode di una posizione soleggiata con vista sulle montagne del Pratomagno. Ideale come base di partenza per visitare in poche ore di auto Firenze, Arezzo, Cortona, Siena e le colline del Chianti. Animali non ammessi.

Superhost

Loft in Loro Ciuffenna

4.76 out of 5 average rating, 174 reviews

La Badia: the unconventional green Tuscany

La Badia loft is an authentic tuscan house surrounded by olive trees and vineyards. It takes the name from the adjacent old church "Badia di Sant'Andrea" which dates back to the 10th century and has been in my family for two generations. Each details and piece of forniture has been choosen by my wife Barbara and me to create a warm comfortable and unique place to stay. Nestled at the foot of the Pratomagno mountain you can choose among lots of activities to do or simply relax.

Top Guest favourite

Farm stay in Loro Ciuffenna

4.99 out of 5 average rating, 106 reviews

Il Roseto: your Villa in Tuscan Countryside

In the heart of Tuscany between Arezzo, Florence and Siena but far away from the bustle of the cities, you will find a pristine landscape where to enjoy nature and relaxing, amazing views and much more for a perfect getaway with your friends or family. A villa of 190 mq with 600 mq garden,where you can enjoy lunch outdoors, have fun making pizza and baking it in the wood- oven, or savour a wonderful barbeque. A comfortable Villa for guests who love being together.

Top Guest favourite

Castle in Ferrano

4.99 out of 5 average rating, 196 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Guest favourite

Condo in San Gimignano

4.93 out of 5 average rating, 119 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Top Guest favourite

Guesthouse in Perugia

4.99 out of 5 average rating, 123 reviews

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Guest favourite

Home in San Giovanni Valdarno

4.98 out of 5 average rating, 101 reviews

FREM House between Chianti Arezzo and Florence

Bright ground floor apartment with garden and separate entrance is located in a quiet and quiet area of the city. It is a few minutes walk from the old town, train station and all amenities. The apartment is very spacious and well furnished internally, it also has a nice outdoor space with exclusive loggia and equipped to spend pleasant breakfasts and lunches outdoors in front of the private garden.

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Other great holiday rentals in Penna

Top Guest favourite

Apartment in Pelago

5 out of 5 average rating, 24 reviews

Barn

KatherineRating, 5 stars3 weeks ago

We loved our stay here!! The view is absolutely beautiful. The apartment had everything we needed and it was super clean. There is also a train station right down the road for an easy train ride into Florence if that is something you are wanting to do. Would definitely recommend staying here!

Apartment in Loro Ciuffenna

5 out of 5 average rating, 3 reviews

Apartment via Dante ,Centro Storico

AntonellaRating, 5 stars1 week ago

Excellent solution for our stay in Loro Ciuffenna... Convenient to reach in a few minutes from the public parking lot. Very kind host and always available for any request. If I return to the area, I will definitely consider this accommodation again.

Home in Castelfranco Piandiscò

5 out of 5 average rating, 3 reviews

Casa Nora Charm

Romina AttiliaRating, 5 stars1 week ago

A corner of paradise immersed in olive trees on the ancient Setteponti. The beautiful house is tastefully furnished and cared for in every single detail. 5 stars 🤩

Guest favourite

Apartment in Loro Ciuffenna

5 out of 5 average rating, 37 reviews

Cozy apartment on the Tuscan vineyard

RobertoRating, 5 stars1 month ago

Giulia and her family have these magnificent apartments surrounded by nature, where everything is made with soul. Photos don’t do justice to the beauty you’ll find here. From the moment you arrive, you feel the love of the villa’s owners: neat vineyards, thoughtful landscaping, flowers, cleanliness—it’s like a fairytale. If you’re looking for a place to relax and enjoy scenic views and birdsong, this is it. The hilltop location offers stunning views, and the grounds include a small church, vineyards, panoramic pool, playground, ping pong table, and a lovely resident donkey named Pedro. We appreciated the coffee machine with capsules for the whole stay, and the welcoming gift of wine and olive oil. Special thanks to Giulia for the amazing winery tour and tasting—we’ll definitely be back!

Guest favourite

Home in Terranuova Bracciolini

5 out of 5 average rating, 16 reviews

Melograno by Interhome

LéoRating, 5 stars2 weeks ago

The place felt like a corner of paradise on Earth, and we immensely enjoyed it. The weather (1st week of June) was perfect, and the house itself never too hot or too cold. The swimming pool area was a haven of peace, all the exterior spaces allowed us to stay in the sun or in the shade whenever we felt like it. It also has the advantage of being located is a beautiful area - in relatively close proximity to Firenze, Sienna, Arrezzo, the Chianti... And beautiful walks around the house if one doesn't feel like driving. Finally, our host, Fioretta, was lovely, welcomed us with some Tuscan specialties and delicacies and Italian coffee, some great advice - all this while not speaking a language in common. Luckily, our favorite translating app saved us. The only downside that I think people should be aware of is that the top bedroom is open to the stairs, and therefore does not benefit from the same privacy as the other two - ideal for children, not so much for a couple.

Top Guest favourite

Farm stay in San Quirico d'Orcia

4.98 out of 5 average rating, 44 reviews

Wine Loft in the vineyards

HilaryRating, 5 stars2 weeks ago

The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.

Guest favourite