Vacation rentals in Poggio ai Grilli

4.94 out of 5 average rating, 18 reviews

A view from an open window showcasing a rustic brick facade. The landscape outside features greenery and terracotta seating arrangements. Soft clouds drift in the blue sky, adding to the serene ambiance of the setting.

Condo in Certaldo

Borgo Antico Residence - Tuscan Charm

Discover the beauty of Tuscany at Borgo Antico Residence, a charming retreat located in the heart of the region, a few kilometers from Florence, Siena and San Gimignano. Here, history and nature intertwine in a captivating way, giving you a unique atmosphere A short walk from Boccaccio's house and the Praetorian Palace, you'll have the opportunity to explore the area's rich cultural heritage. Immerse yourself in breathtaking landscapes featuring green hills, vineyards and olive groves surrounding the village.

Farm stay in San Gimignano

The historic towers of San Gimignano are illuminated against a dark sky, highlighting their distinctive architecture. The surrounding buildings are softly lit, creating a serene nighttime atmosphere that emphasizes the town's medieval character.

4.89 out of 5 average rating, 208 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

Vacation home in Petriccio

A small table with two folding chairs is set on lush green grass, providing a serene spot for relaxation. The scenic view features rolling hills and a cloudy blue sky, creating a peaceful outdoor atmosphere. The area is surrounded by greenery.

4.78 out of 5 average rating, 67 reviews

Garden overlooking Tuscan hills

Apartment with a view of Certaldo Alto, the medieval village of Boccaccio, nestled in the Tuscan hills. Equipped with two spacious double bedrooms, both with 32-inch Smart TVs, a living room with a comfortable double and single sofa bed, a bathroom, and a fully equipped kitchen. Free parking always available on-site and a garden with a view. Pietra Giglia is located precisely between Florence and Siena. Also easily reachable are San Gimignano, Volterra, and Monteriggioni

4.99 out of 5 average rating, 276 reviews

Apartment in Poggibonsi

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

4.93 out of 5 average rating, 118 reviews

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

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.

4.91 out of 5 average rating, 323 reviews

Apartment in Gavignano

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 378 reviews

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. 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.

The entrance is framed by tall, neatly trimmed cypress trees lining a gravel path. Stone pillars support an archway at the drive's beginning, leading into a serene countryside view with softly rolling hills in the background.

4.89 out of 5 average rating, 108 reviews

Tenuta di Pomine Certaldo (FI) Papavero Apartment

Apartment of three rooms 65 m2 on the first floor. Tasteful decor: 1 double bedroom, 1 bedroom with two beds, kitchen (4 cooking points), oven, refrigerator, freezer, dishwasher, microwave, TV, Wifi. Bathroom with shower,sink, bidet,toilet. Beautiful panoramic view over the countryside. Linen change/week. Accommodation tax 2 euros per day per person to be paid upon arrival for the first 6 days (from 14 years old )

A round table is set with a large planter featuring an assortment of succulent plants. In the background, rolling hills covered in vineyards extend under a blue sky with wispy clouds, creating a serene rural landscape.

4.94 out of 5 average rating, 17 reviews

Tuscany Hills View 1

Relax in this quiet accommodation. Newly renovated modern apartment immersed in the countryside with communal pool above ground 6M x 2.5 M outdoor space where you can eat. Composed of a double bedroom, double sofa bed in the living room, kitchen with stove, oven, microwave, fridge, kettle, coffee maker, dishwasher, full bathroom. TV, free Wi-Fi, air conditioning, free parking and electric vehicle charging.

4.96 out of 5 average rating, 249 reviews

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

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.

Home in Tavarnelle Val di Pesa

4.96 out of 5 average rating, 296 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

A charming balcony is featured, adorned with colorful flowers and greenery along the wall. A small wooden table and two foldable chairs are positioned against the wall, while a planter brimming with pink flowers sits nearby, creating a pleasant outdoor space.

4.97 out of 5 average rating, 112 reviews

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

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Other great vacation rentals in Poggio ai Grilli

4.96 out of 5 average rating, 24 reviews

Two glasses of red wine are clinked together, emphasizing a celebratory moment. A neutral table setting with a linen tablecloth is visible, featuring a dark plate of green grapes and minimalist tableware, creating an inviting dining atmosphere.

Condo in Certaldo

Poggio ai Grilli Apartment

GiuliaRating, 5 stars3 weeks ago

Veronica, the host, is very helpful and attentive to the needs of the customer... well-equipped kitchen and clean and tidy linen. I really appreciated the breakfast that was left for us and the bowls + blanket for our dog! In the apartment, you will find everything you need, just bring the bare minimum!

Home in Certaldo

4.67 out of 5 average rating, 3 reviews

Cut to Bagnano - Ponente

ClaudioRating, 5 stars10 months ago

Cozy retreat amidst olive trees. Lovely garden and pool. Pleasant AC. We had a good time.

A garden area features a large, well-maintained lawn with several sunloungers positioned for comfort. Flowering plants are arranged in terracotta pots, and olive trees adorn the backdrop. A view of the surrounding countryside and medieval town towers is visible in the distance.

Cottage in San Gimignano

4.88 out of 5 average rating, 105 reviews

Countryside Cottage With View - Le Papere apt

RamseyRating, 5 stars2 weeks ago

Amazing place, big garden and amazing view. Will be back for sure

The image showcases the Leaning Tower of Pisa, viewed from a low angle, emphasizing its distinctive tilt. The tower's white marble façade is adorned with arches and columns, set against a backdrop of dramatic clouds painted in soft hues of blue and orange.

5 out of 5 average rating, 4 reviews

La Capinera

AlessandraRating, 5 stars2 weeks ago

Very clean apartment, with attention to detail. Excellent communication with the owner; very kind and helpful, it's a shame we couldn't meet in person. Certaldo is a small town, very beautiful and strategic as a location to visit Siena, Florence, San Gimignano, etc. We will definitely be back!! THANKS FOR EVERYTHING!

4.89 out of 5 average rating, 19 reviews

Apartment in Montebello

Montebello, Tuscan Heart

Jean RenéRating, 5 stars3 days ago

Pleasant and ideally located accommodation for visiting the beautiful region of Tuscany and its wonderful cities accessible by train (train station 5 min and train every hour).

An outdoor terrace is visible, featuring a table set for two with wine glasses and a bottle. Lush greenery and rolling hills can be seen in the background, illuminated by the soft light of sunset.

Apartment in San Gimignano

5 out of 5 average rating, 4 reviews

Apartment in San Gimignano - Cipresso

SilviaRating, 5 stars6 days ago

We had a wonderful stay on this charming hill right in front of San Gimignano. The view is simply breathtaking, at any time of day. The accommodation is in a very quiet area, surrounded by nature and total peace, ideal for those looking for relaxation and authenticity. A special thank you to Renata for her warm hospitality and to her son Orlando, who made us discover new and authentic flavors of this very special Poggio. An experience that we will carry in our hearts! We highly recommend a visit and tasting at the Casa Lucii winery. We'll definitely be back!!

4.92 out of 5 average rating, 263 reviews

Cottage in Montespertoli

Lovely countryhouse on Chiant hills

CynthiaRating, 5 stars1 week ago

Antonella’s is a charming, quiet, and comfortable home in the Tuscan hills. We enjoyed many lovely meals on the deck overlooking the countryside during our two week stay. A car and a good navigation system are necessary here. Many small medieval towns, Florence, and the beaches are an hour or more away. If you park in one of lots on the outskirts of Florence, you can take the train or bus into the city to avoid parking downtown where it’s very crowded. The nearby towns, such as San Gimignano, Vinci, Deruta (the spot to buy pottery) all have public parking lots. If you appreciate quiet and quaint away from crowds, this is the place!