Vacation rentals in Quercegrossa

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Top-rated vacation rentals in Quercegrossa

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Guest favorite

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

Villa in Castellina in Chianti

4.93 out of 5 average rating, 214 reviews

The Farmhouse Cottage

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Top guest favorite

The view from the window highlights a lush garden with a swimming pool surrounded by tall cypress trees. A grassy area features shaded seating, inviting relaxation in a serene landscape. The sky is bright with scattered clouds, enhancing the peaceful atmosphere.

Apartment in Asciano

4.97 out of 5 average rating, 150 reviews

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

Top guest favorite

The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.

Apartment in Siena

4.99 out of 5 average rating, 158 reviews

Villa di Geggiano – Alfieri Suite

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Superhost

The image depicts a serene pool area surrounded by lush greenery and trees. Comfortable lounge chairs are positioned around the pool, and several umbrellas provide shade. A stone pathway leads down to the pool from an elevated area, enhancing the natural setting.

Farm stay in Monteriggioni

4.82 out of 5 average rating, 148 reviews

Podere Casalino - La Pergola

Nestled near the enchanting Monteriggioni Castle, "Il Casalino" embodies our passion and dedication to restoring a historic farmhouse. My husband and I have poured our hearts into crafting two apartments for rent: Il Gatto and La Pergola. If you have any questions, please reach out to me. Your inquiries are of the utmost importance, and I am committed to promptly responding to your messages. We eagerly anticipate the opportunity to welcome you to "Il Casalino" soon! Best regards, Laura

Top guest favorite

Villa in Siena

4.98 out of 5 average rating, 185 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Top guest favorite

An industrial-style kitchen and dining area are showcased, featuring a wooden table surrounded by modern chairs. Unique pendant lights illuminate the space, which includes sleek cabinets and stainless steel appliances. A staircase leads to a mezzanine, adding depth to the open layout.

Loft in Siena

4.95 out of 5 average rating, 377 reviews

Cri's Loft with a view and parking space

Here you’ll find a very nice loft, furnished in an industrial style. It has private access, a private parking space and a courtyard with hedges and a table for you to enjoy your breakfast and a book. You can enjoy a beautiful view of the countryside of Siena and the view of the Torre del Mangia. It is located only 2 minutes from Porta Pispini, the oldest door of the city, sheltered from the noise of the historic center. Walk just 10 minutes to reach the beautiful Piazza del Campo.

Guest favorite

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

4.93 out of 5 average rating, 118 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.

Guest favorite

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

Condo in Castelnuovo dell’Abate

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Top guest favorite

A serene salt-water pool is surrounded by lush greenery and colorful flowers. Sun loungers are positioned around the pool, offering seating for relaxation. Rolling hills and cypress trees create a picturesque backdrop, showcasing the tranquil beauty of the Tuscan countryside.

Condo in Panzano

4.96 out of 5 average rating, 249 reviews

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

Guest favorite

Farm stay in Simignano

4.89 out of 5 average rating, 196 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favorite

Condo in Bivio Santo Stefano

4.98 out of 5 average rating, 120 reviews

Agriturismo Osea, Sunset flat

Relax with the whole family in this peaceful accommodation, nestled in the Tuscan countryside, 10 minutes drive from Siena and the Monteriggioni castle, very close to the Francigena route and the Chianti hills. Very suitable for families with children and for those who want to immerse themselves in country life.

Top guest favorite

The exterior features a rustic stone façade, complemented by wooden shutters. A small outdoor seating area with minimal furniture is visible. The entrance showcases double doors leading into the apartment, surrounded by greenery and the bare branches of a tree against a clear sky.

Condo in Monteriggioni

4.92 out of 5 average rating, 122 reviews

Il Vecchio Noce

In the ancient rural complex of Caggio, “Il vecchio noce” offers a fully renovated apartment that can accommodate 2 to 4 people. The complex is located in the heart of the Tuscan countryside, on the Sienese Montagnola, near the medieval village of Monteriggioni and the Via Francigena route.

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Other great vacation rentals in Quercegrossa

Top guest favorite

Home in Panzano

4.98 out of 5 average rating, 439 reviews

Old Farmhouse near Panzano Castle Abbacìo

MarthaRating, 5 stars2 days ago

Our stay was exceptional in every way! This is the best spot in the best location in Tuscany! Nicoletta and Stefano are excellent hosts and are always available and responsive. The house is spacious and beautifully appointed with everything you could possibly need. The house is decorated so beautifully and the grounds are covered in flowers. The incredible view and easy access to the lovely village make this a must see. We cannot wait to come back!

Guest favorite

Villa in Quercegrossa

4.97 out of 5 average rating, 67 reviews

Le Redi holiday villa in Chianti Classico, Tuscany

AprilRating, 5 stars1 month ago

Such a beautiful location, such a beautiful home. The views from inside the house and outside on the patios and in the yard were quintessential Tuscany, gorgeous beyond belief. The kitchen was well stocked with plenty of dishes and flatware and pots and pans. The furnishings were tasteful and plentiful. We were a group of four women. One of us slept upstairs in the area just off the front door. Just a note: one of our party did not do stairs very well, and just so you know, all of the bedrooms on the lower level have doors that open onto the patio area, which is right next to the driveway. So after the first day, when we figured all that out, she was able to reduce the number of stairs she had to climb to a minimum. She would climb up to the kitchen and the living room area when we were gathering, but there was a bathroom and shower on the main level and whenever we went out to the car, she just came out that way, & one of the others of us would lock the door and run upstairs to leave.

Top guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 420 reviews

Farmhouse Fattoria La Parita

NatalliaRating, 5 stars2 days ago

We spent time in a stunning place. Beautiful, cozy, like home. Sandra is very hospitable. The breakfast she prepared was very tasty. I highly recommend it.

Top guest favorite

A window view frames the serene landscape, showcasing rolling green hills and vineyards under a partly cloudy sky. A bottle of wine and two wine glasses rest on the windowsill, adding to the tranquil atmosphere of the scene.

Apartment in Pievescola

4.99 out of 5 average rating, 107 reviews

Tuscan View 360: 3 bedr, 2 baths, free parking

BalkarRating, 5 stars6 days ago

Very clean Airbnb, the host left us with a bottle of wine and brownies for our arrival which was very thoughtful. The Tuscan views from the bnb was very nice.

Guest favorite

An expansive view of a serene outdoor setting, featuring a sparkling swimming pool surrounded by neatly arranged sun loungers. Lush gardens and trees in vibrant bloom provide a natural backdrop against a rustic stone building set atop a hill, with a blue sky adorned by soft, white clouds.

Vacation home in Vitignano

4.97 out of 5 average rating, 34 reviews

Podere Vittoria Apartment: Heart of Chianti

CraigRating, 5 stars1 week ago

We absolutely loved this apartment, it was spacious and spotless, with modern bathrooms and the most perfect “farmhouse” kitchen. The view from the apartment and infinity pool was breathtaking. It’s the best Airbnb we have stayed in!

Guest favorite

A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.

Home in Castellina in Chianti

4.98 out of 5 average rating, 99 reviews

Explore Chianti from a Charming Stone House

ShelbyRating, 5 stars3 days ago

Best part of our Italy trip! We loved our stay at Casa Marinella, and Monica has thought of every detail to make for a wonderful and peaceful vacation! Relax by the pool and enjoy breathtaking views. Be sure to stop by Gelateria di Castellina for a scoop of cremino gelato and try the fiorentina steak at Osteria La Sosta di Pio VII.

Top guest favorite

A modern bathroom sink is featured, showcasing a white basin set on a wooden countertop. A sleek faucet is positioned above, with a soft white towel hanging nearby. Neutral-colored tiles adorn the walls, contributing to an open and clean appearance.

Apartment in Siena

4.97 out of 5 average rating, 32 reviews

Palazzo del Papa Standard Suites

TravisRating, 5 stars3 weeks ago

AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.

Top guest favorite

Condo in Noce

5 out of 5 average rating, 150 reviews

Ancient Farmhouse in Chianti with Panoramic Pool

KarenRating, 5 stars6 days ago

If you’re wondering why this place has so many 5-star reviews, it’s because it offers the most heartfelt, attentive service we’ve ever received. This lovingly restored 6th-century Tuscan farmhouse—with a pristine saltwater pool, breathtaking views, and traditional charm—was only part of what made our stay unforgettable. The hosts created magical, personal experiences: truffle hunting with Mattia and his father and their dogs, wine tasting with Niccolo at a nearby family-run vineyard, and a Tuscan steak feast grilled over a woodfire. Each moment was filled with warmth, joy, and generosity—from Silvia’s homemade truffle pasta to the family’s own wine served with every meal. We laughed, explored, and connected deeply with a family that clearly loves what they do. It wasn’t just a stay—it was an experience we’ll never forget. We can’t wait to return.

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Vacation rentals in Quercegrossa

Top-rated vacation rentals in Quercegrossa

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