Vacation rentals in Valpiana

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Top-rated vacation rentals in Valpiana

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Guest favorite

Loft in Massa Marittima

4.88 out of 5 average rating, 154 reviews

Authentic Cave House in the heart of the Village!

The house is in the heart of Massa Marittima, a medieval village which is setting on the top of a hill in the Maremma countryside. This authentic historical small town is short driving distance from many amazing beaches of the Mediterranean coast: Cala Violina, Torre Mozza, the Baratti Etruscan Riviera.. Ideal for a romantic escape but also for those who are looking for a local experience in a relaxed, suggestive, historical context far away from mass tourist routes. PLEASE READ ALL DESCRIPTION!

Sep 18 – 25

G$24,089 GYD per night

Guest favorite

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 27 – Jan 3

G$22,862 GYD per night

Guest favorite

Home in Peccioli

4.99 out of 5 average rating, 112 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.

Jul 13 – 20

G$33,408 GYD per night

Guest favorite

Apartment in Siena

4.99 out of 5 average rating, 136 reviews

Villa di Geggiano - Alfieri Suite

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.

Jan 19 – 26

G$71,203 GYD per night

Guest favorite

Apartment in Caminino

4.92 out of 5 average rating, 128 reviews

Pieve di Caminino Historic Farm

L'antica fattoria Pieve di Caminino, oggi biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due antiche strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Oct 24 – 31

G$37,491 GYD per night

Guest favorite

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.

Oct 7 – 14

G$33,380 GYD per night

Guest favorite

Farm stay in Seggiano

4.98 out of 5 average rating, 193 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.

Jan 18 – 25

G$22,911 GYD per night

Guest favorite

Condo in Massa Marittima

4.99 out of 5 average rating, 153 reviews

Casa Vecchio Forno

The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from Piazza del Duomo. It is easily accessible from all the car parks of the historic center and within walking distance you can find: bars, restaurants, banks, groceries, a pastry shop and a pharmacy. The house recently renovated, has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

May 17 – 24

G$18,763 GYD per night

Guest favorite

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)

Mar 15 – 22

G$38,679 GYD per night

Guest favorite

Guest suite in Greve in Chianti

4.94 out of 5 average rating, 380 reviews

Selvabella in Chianti B&B. Suite Lo Scricciolo

Lo Scricciolo is located in the tower, the highest building of the house. By a separate entrance from the main house, through a loggia overlooking the Tuscan countryside, you access the first floor. Here are the living room with wooden ceiling and a small bathroom. From the living room, an old stone staircase leads to the upper floor where there is a large double bedroom. Lo Scricciolo has an efficient system of heating for the cold season.

Oct 12 – 19

G$25,456 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 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.

Nov 30 – Dec 7

G$33,093 GYD per night

Guest favorite

Tower in Fiesole

4.95 out of 5 average rating, 153 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Sep 20 – 27

G$181,203 GYD per night