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Vacation rentals in Montescudaio

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montescudaio

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

Guest favorite

Condo in Noce

5.0 out of 5 average rating, 117 reviews

Vergianoni estate nestled in the Chianti with a pool

Podere Vergianoni is located in the beautiful hills of Chianti. The apartment is furnished in perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and unique, handcrafted furniture. Inside you will find a large living room with kitchen ,sofa bed , a bathroom and a bedroom with double bed. In the large outdoor courtyard you will find at your disposal a swimming pool on a breathtaking terrace where you can enjoy a wonderful view of the view with unique sunsets!

Jan 30 – Feb 6

R2,303 ZAR per night
Guest favorite

Home in Peccioli

4.99 out of 5 average rating, 111 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.

Nov 2 – 9

R2,964 ZAR per night
Guest favorite

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.

Mar 8 – 15

R9,491 ZAR per night

Popular amenities for Montescudaio vacation rentals

Stay near Montescudaio's top sights

Osteria BardoVino10 locals recommend
Osteria Pizzeria Il Forapaglia4 locals recommend
Ristorante Il Frantoio12 locals recommend

Other great vacation rentals in Montescudaio

Guest favorite

Apartment in Montescudaio

4.9 out of 5 average rating, 49 reviews

La Suite del Borgo

Oct 22 – 29

R1,179 ZAR per night
Guest favorite

Home in Montescudaio

4.96 out of 5 average rating, 90 reviews

Open space immersed in nature

Nov 19 – 26

R3,038 ZAR per night
Guest favorite

Guest suite in Cecina

4.9 out of 5 average rating, 42 reviews

The nest in Tuscany

Oct 30 – Nov 6

R1,876 ZAR per night
Guest favorite

Home in Casale marittimo

4.95 out of 5 average rating, 59 reviews

La Baciosa, an unforgettable view.

Jan 29 – Feb 5

R3,163 ZAR per night
Guest favorite

Home in Guardistallo

4.79 out of 5 average rating, 24 reviews

Independent house with garden

May 22 – 29

R1,383 ZAR per night
Guest favorite

Vacation home in Riparbella

4.96 out of 5 average rating, 27 reviews

Tuscan countryside & pool - 20 min from the beach

Oct 15 – 22

R10,269 ZAR per night
Superhost

Home in Riparbella

4.9 out of 5 average rating, 10 reviews

Gorgeous cottage with infinity pool

Dec 8 – 15

R8,263 ZAR per night
Guest favorite

Home in Rio Marina

5.0 out of 5 average rating, 55 reviews

Casa del Capitano | Monte Grosso, Elba

Nov 2 – 9

R8,090 ZAR per night
Superhost

Castle in Sassa

4.93 out of 5 average rating, 15 reviews

Torre Sassa - Intera Torre Medievale

Feb 10 – 17

R9,626 ZAR per night
Guest favorite

Castle in Montecatini Val di Cecina

4.99 out of 5 average rating, 87 reviews

Torre dei Belforti

Apr 25 – May 2

R13,325 ZAR per night
Guest favorite

Villa in Marina di Bibbona

4.96 out of 5 average rating, 23 reviews

Casa Rosa - Villa with private access to the beach

Oct 22 – 29

R16,464 ZAR per night
Guest favorite

Villa in Peccioli

5.0 out of 5 average rating, 23 reviews

Campo Alle Lucciole: Entire Tuscan Stonehouse

Nov 30 – Dec 7

R2,725 ZAR per night

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Pisa
  5. Montescudaio