Vacation rentals in Montaio

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 ...

Guest suite in Greve in Chianti

4.97 out of 5 average rating, 395 reviews

Selvabella in Chianti B&B Il Riccio

Selvabella is a farmhouse situated in the heart of Tuscany, half way between Greve and Panzano in Chianti. Just 35 km from Florence and Siena it is a perfect place to enjoy the beauty of Chianti. Il Riccio is an apartment of 45 square meters. It has a double bedroom, a living-room/bedroom with two sofas/ single beds, a large bathroom and a kitchenette (fridge, sink, small oven and 2 buners gsafire). It is the perfect place for lovers of nature, cooking and pottery.

Apartment in Barberino Val d'Elsa

4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

The apartment delle Rose is located inside the guest house Mulino dell 'Argenna. The structure was completely restored in 2015. It is a former stone mill dating back to 1400, built along the course of the Borro dell 'Argenna. Il Mulino is an enchanting place, immersed in the green of the forest, with a beautiful park of one hectare and a large swimming pool. An ideal place to spend your days in Tuscany in maximum privacy, in full contact with nature.

4.93 out of 5 average rating, 118 reviews

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.

4.85 out of 5 average rating, 71 reviews

Cottage in Cavriglia

Il Fienile, characteristic stone cottage for 2

This quaint cottage was once used as a barn, and still maintains the old stone walls, terracotta floor and exposed beamed ceiling. It has a decidedly rustic character but the period furniture, a family legacy, gives it personality and a certain distinction. Outside it has a covered area surrounded by a hedge, and all the space around - lawn and olive trees - equipped with table, chairs, bbq, umbrella, deckchairs and sun loungers.

4.96 out of 5 average rating, 249 reviews

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.

4.91 out of 5 average rating, 43 reviews

Tiny home in Cavriglia

Chalet at the gates of Chianti

If you don't like crowded places my camping can be the answer .In the real and quiet tuscan countryside, really near to Chiant,i only two chalet ,not more than six people in total. The near village,Cavriglia, is within easy walking distance and it is provided with essential services. A pool for the hottest days. Free access to my organic vegetable garden when is in production

4.89 out of 5 average rating, 198 reviews

Farm stay in Simignano

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!

4.99 out of 5 average rating, 133 reviews

Villa in Cavriglia

Villa Poggio in Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

4.95 out of 5 average rating, 192 reviews

Condo in Montevarchi

Art-Design Fienile in the heart of Tuscany

The “Fienile”, like all apartments at La CasA sul SentierO, has been renovated with respect for traditional forms and materials, following the principles of bio-architecture. It features a spacious bedroom with valley view, a large living room, a well-equipped kitchen with cooking area, a wide bathroom with double shower, and a private garden to relax outdoors.

Farm stay in Gaiole in Chianti

4.94 out of 5 average rating, 233 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Farm stay in Gaiole in Chianti

4.95 out of 5 average rating, 103 reviews

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2

Beautiful charming 1 bedroom ground floor apartment in the Le Miccine villa. Surrounded by vines and nature. Ideal location for visiting Tuscany or relaxing by the pool. Wine tasting on site and helpful staff. We are classified as a 4 Sunflower Agriturismo.

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4.94 out of 5 average rating, 89 reviews

Apartment in Pogi

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago

5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!

Home in Gaiole in Chianti

4.94 out of 5 average rating, 32 reviews

Casina del Chianti

SabineRating, 5 stars1 month ago

We had a great stay in la Casina! The view from the garden is just what you expect from Tuscany and the place is ideal for a calm and relaxing stay. The kitchen is well-equipped and there are a lot of nice extras to explore (the vinyl collection, a guitar etc.). Edoardo had lots of good suggestions for the area and was great host! Highly recommended :)

Farm stay in San Giovanni Valdarno

4.81 out of 5 average rating, 69 reviews

Cozy Tuscany Farmhouse Apt

JonahRating, 5 stars9 months ago

a beautiful apartment. the parents were really nice and endeavoured even though there is a language barrier:) the location is good when you are with a car otherwise it’s nearly impossible to move around the area:) The fact it’s possible to harvest several herbs out of the garden (for free) is a in incredible detail.! all in all a very good experience, hopefully we will come back! kind regards from germany<3

Vacation home in Greve in Chianti

4.9 out of 5 average rating, 20 reviews

Cuculo - Rifugium

KlioRating, 5 stars2 months ago

Beautiful apartment in the countryside. Spacious and clean. The access by car was a little difficult but definitely recommended.

4.92 out of 5 average rating, 24 reviews

Home in Selvole

Chianti House on the woods

CarolineRating, 5 stars1 week ago

We had everything we needed for a very relaxing stay in rural Tuscany, away from the hustle and bustle of daily life. Our hosts, Alejandra and Filippo, were very welcoming, friendly and helpful with local recommendations.

Home in Cavriglia

4.89 out of 5 average rating, 27 reviews

Between Florence, Arezzo, Siena at the gates of Chianti

KurtRating, 5 stars25 months ago

Paola’s place was exactly as described. Beautifully furnished, extremely clean, and had all amenities you would need. Paola fixed the shower head and provided a fan immediately upon request. Only cons would be that there is not anything to do nearby, only a couple of places to eat, and parking is an issue if arriving at the apartment at the end of a long day. The restaurant at the end of the street is fantastic!

Farm stay in Greve in Chianti

4.98 out of 5 average rating, 59 reviews

Casa Giulia di Sopra Farmhouse

DarioRating, 5 stars3 weeks ago

What a great winery! The location is really unique, the accommodation is in the middle of the vineyard and very quiet. Alessandro our host was very nice, gave us a warm welcome and took a lot of time to show us everything (including the wines). We were also very happy with the accommodation, which was beautifully furnished and had everything we needed.