Vacation rentals in Penna

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Top-rated vacation rentals in Penna

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Top guest favorite

The entrance of Villa Piandarca is framed by lush greenery and decorative pots. A rustic wooden door stands partially open, revealing a white curtain gently flowing in the breeze. The building's warm yellow exterior adds to the inviting atmosphere of the property.

Home in Terranuova Bracciolini

Villa Piandarca - Tuscany - WIFI - private pool

The Villa Piandarca is, situated in a panoramic place, immersed among the vineyards of the Tuscan countryside, and in a strategic position between Firenze, Siena and Arezzo. It consists of two apartments with separate entrance from the garden. The villa has a total capacity for 10 people and each apartment has a kitchenette with dish washer and air-conditioning in all rooms, wifi and veranda. The villa has also large outdoor areas and a beautiful salt water swimming pool where guests can relax.

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4.98 out of 5 average rating, 57 reviews

Guest favorite

An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.

Home in Casale

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

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4.88 out of 5 average rating, 201 reviews

Top guest favorite

A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.

Farm stay in Ruscello

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

ValueFamilyNearby

4.99 out of 5 average rating, 526 reviews

Top guest favorite

A charming countryside villa displays traditional stonework, surrounded by lush green fields and trees. The main building features classic Tuscan architecture, while a smaller guest house is positioned nearby, both offering an inviting and serene environment amidst nature.

Home in Campogialli

Salceta a Tuscany Country House Private Pool & BBQ

A typical style stone villa set in the Valdarno area on a private estate. The villa is the ideal vacation solution for a group of friends or for a family reunion in a context of total privacy. In the outdoor the swimming pool, the dining area under a pergola and BBQ. A meticulous restoration, using high quality materials and attention to detail in fabrics and furniture, has conveyed a sense of beauty and elegance to the house, leaving unchanged the genuineness and warmth of Tuscan farhouses.

FamilyLocationQuiet

4.97 out of 5 average rating, 35 reviews

Top guest favorite

Home in Greve in Chianti

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

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4.99 out of 5 average rating, 113 reviews

Top guest favorite

An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.

Villa in Loro Ciuffenna

The Lazy Oak

Perched on a hillside above the Valdarno area, between the cities of Florence, Arezzo and Siena, the Lazy Oak villa is surrounded by acres of olive groves. The main house on two level has been fitted with bedrooms, bathrooms and new kitchen whilst retaining its old terracotta floors and beamed ceilings. A dining loggia for al fresco meals enjoys a breathtaking view of the countryside. The infinity pool is set just a few steps from the house on a green terrace furnished with loungers.

FamilyLocationHospitality

4.97 out of 5 average rating, 71 reviews

Guest favorite

A well-appointed sleeping area features a spacious bed adorned with a patterned duvet. Soft pillows provide comfort, and a bedside lamp offers warm illumination. Exposed wooden beams add character to the ceiling, and a framed artwork is displayed on the wall.

Farm stay in Terranuova Bracciolini

Charming B & B in Tuscany farmhouse

Exclusive Privacy You will be the only guests at the property, enjoying exclusive access to the entire suite, the private garden with a gazebo, and a charming direct access to the Ciuffenna stream. An oasis of peace and privacy designed for those seeking a relaxing stay immersed in nature. Welcome Basket The property does not serve breakfast. However, upon arrival, we will be happy to welcome you with a delightful WELCOME BASKET containing everything you need for breakfast.

FamilyLocationComfort

4.96 out of 5 average rating, 73 reviews

Top guest favorite

The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.

Farm stay in Loro Ciuffenna

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.

FamilyLocationKitchen

4.99 out of 5 average rating, 123 reviews

Top guest favorite

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

FamilyValueAccuracy

4.98 out of 5 average rating, 105 reviews

Superhost

A spacious, well-equipped kitchen features wooden cabinetry and a gas stove. Light neutral walls provide a warm backdrop, complemented by a rustic dining table and high stools. Chalkboard art adds an artistic touch, and a kettle on the stove suggests functionality.

Vacation home in Terranuova Bracciolini

Casa Canto alla Luna Piscina WiFi Orto & Giardino

In the center of a small historic village, surrounded by nature and hills. From here, right in front of our houses, the peasants once passed by singing the May song, thus welcoming the arrival of spring. Our vegetable garden is located just above the ancient village, here every season works its magic, we grow the plants and vegetables that we use to prepare the dishes for our cooking classes. Welcome, warmth and comfort are the ingredients of our hospitality.

LocationFamilyCondition

4.96 out of 5 average rating, 45 reviews

Guest favorite

Home in Pogi

Private Cottage with Plunge Pool in Tuscan Estate

A private cottage with garden and plunge pool, set within Borgo Iesolana Estate. Perfect for up to 6 guests, yet equally special for couples. Enjoy total privacy, a fully fenced garden (ideal for dogs), stunning views and an exclusive plunge pool — with breakfast included and full access to the Borgo’s pools, restaurant and bar just a short walk away. Private parking, Wi-Fi, TV, air conditioning, heating and a fully equipped kitchen complete the experience.

LocationAccuracyCondition

5.0 out of 5 average rating, 10 reviews

Top guest favorite

A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.

Farm stay in Greve in Chianti

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

ValueLocationComfort

4.99 out of 5 average rating, 431 reviews