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Vacation rentals in Montemassi

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montemassi

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 103 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. 4 – 11

$917 CAD per night
Guest favourite

Apartment in Montepulciano

4.97 out of 5 average rating, 327 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Feb. 22 – Mar. 1

$221 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.

Feb. 27 – Mar. 6

$181 CAD per night

Popular amenities for Montemassi vacation rentals

Other great vacation rentals in Montemassi

Guest favourite

Villa in Ambra

4.98 out of 5 average rating, 107 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Mar. 16 – 23

$1,183 CAD per night
Guest favourite

Cottage in Chianni

4.98 out of 5 average rating, 116 reviews

La Pietruzza - The Private Chalet with a Soul -

Feb. 10 – 17

$245 CAD per night
Guest favourite

Cottage in San Gimignano

4.94 out of 5 average rating, 246 reviews

Small renovated barn

Jan. 15 – 22

$147 CAD per night
Guest favourite

Condo in Massa Marittima

4.99 out of 5 average rating, 153 reviews

Casa Vecchio Forno

Dec. 21 – 28

$122 CAD per night
Guest favourite

Condo in Montemassi

5.0 out of 5 average rating, 22 reviews

Babe and Madde's house, air-conditioned environment

Jan. 6 – 13

$83 CAD per night
Guest favourite

Apartment in Montemassi

4.97 out of 5 average rating, 72 reviews

" from Huesa" IN the heart OF the Maremma

Jul. 7 – 14

$75 CAD per night
Guest favourite

Vacation home in Montemassi

5.0 out of 5 average rating, 13 reviews

Townhouse

May 3 – 10

$84 CAD per night
Guest favourite

Apartment in Montemassi

4.91 out of 5 average rating, 93 reviews

Montemassi, the Maremma that enchants the House of Arts

May 10 – 17

$92 CAD per night
Guest favourite

Apartment in Montemassi

4.96 out of 5 average rating, 80 reviews

Casa Sabina

Jun. 14 – 21

$78 CAD per night
Guest favourite

Vacation home in Montemassi

4.97 out of 5 average rating, 30 reviews

CaRe's Home

Feb. 1 – 8

$98 CAD per night
Guest favourite

Home in Montemassi

4.9 out of 5 average rating, 21 reviews

Holiday home "Zia Patrizia" in Montemassi

Jul. 11 – 18

$90 CAD per night
Guest favourite

Apartment in Roccatederighi

5.0 out of 5 average rating, 8 reviews

Apartment with pool - max 3 people

Jul. 1 – 8

$217 CAD per night

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Montemassi