Vacation rentals in Montemassi

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Top-rated vacation rentals in Montemassi

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Guest favourite

Farm stay in Ruscello

4.99 out of 5 average rating, 323 reviews

Agriturismo Fattoria La Parita

Provençal-style apartment nestled between the 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. It includes a basic Italian breakfast (coffee, tea, milk, cookies, etc.) that you can prepare on your own, if you want to try one of the famous breakfasts prepared and served by Sandra, the cost is €10 per person (6€ 5 to 15 years)

Nov. 17 – 24

$202 CAD per night

Guest favourite

Home in Panzano In Chianti

4.98 out of 5 average rating, 354 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!

Dec. 23 – 30

$161 CAD per night

Guest favourite

Home in Peccioli

4.99 out of 5 average rating, 113 reviews

A breathless view

Placed halfroad between Florence and Pisa this Airbnb has a large terrace and a hanging garden. All of this is set against a backdrop of endless hills. It is like a living and eternal painting, where one is not a spectator but an actor and part of a film scene. Being North East here every morning the sun appears on the horizon behind the last strip of green hills while white brushstrokes of mist melt into the air as the red ball rises into the sky. It is a sight that takes one's breath away.

Dec. 7 – 14

$230 CAD per night

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 109 reviews

Villa di Geggiano - Guesthouse

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.

Nov. 7 – 14

$833 CAD per night

Guest favourite

Cottage in Vetulonia

4.96 out of 5 average rating, 115 reviews

La Dolce Vita ~ romantic retreat in quiet nature

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has six unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Mar. 20 – 27

$184 CAD per night

Guest favourite

Farm stay in Seggiano

4.98 out of 5 average rating, 194 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Oct. 13 – 20

$153 CAD per night

Guest favourite

Apartment in Caminino

4.92 out of 5 average rating, 131 reviews

Pieve di Caminino Historic Farm

The ancient Pieve di Caminino farm, now organic, is an important historical site: a former medieval village at the intersection of two ancient Roman streets, it hosted two saints (the 12th century church is now a private museum, which can be visited by guests by appointment). Today it covers 200 acres of gated private property, located on a scenic hill. Seven homes share an estate with a (seasonal) pool, two ponds, a century-old olive grove, vineyard, and a cork forest.

Oct. 14 – 21

$328 CAD per night

Guest favourite

Cottage in Chianni

4.98 out of 5 average rating, 118 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3)

Feb. 17 – 24

$248 CAD per night

Guest favourite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 242 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.

Apr. 27 – May 4

$216 CAD per night

Guest favourite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 202 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Dec. 19 – 26

$217 CAD per night

Guest favourite

Home in Monticchiello

4.97 out of 5 average rating, 135 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Jul. 12 – 19

$453 CAD per night

Guest favourite

Apartment in Monticchiello

4.99 out of 5 average rating, 299 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Mar. 13 – 20

$353 CAD per night