Montalcino vacation rentals

An intimate covered terrace features a wooden table accompanied by two metal chairs, providing a serene space for outdoor dining. The area is framed by wooden beams and overlooks lush greenery, extending towards rolling hills in the distance.

5 out of 5 average rating, 12 reviews

Pompana Rustic Charm Casale

Scopri con Wp Relais l'incanto di Pompana, un antico borgo etrusco immerso nelle colline toscane, dove abbiamo trasformato un vecchio rudere in pietra in una splendida casa rurale indipendente su due piani. Al piano terra, un'accogliente area living open space offre un angolo salotto con camino, una cucina con tavolo da pranzo e un grazioso bagno di servizio. Dal piano terra, accedi a un intimo terrazzo coperto da tettoia con vista panoramica, ideale per pranzi e cene immerse nella natura.

The image captures a serene morning scene with a swimming pool reflecting soft sunlight. Surrounding greenery includes tall cypress trees and leafy shrubs, while gently rolling farmland can be seen in the background, creating a peaceful vibe. The sky is clear with a hint of fog.

4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

Villa La Quercia is a private 2 acre property consisting of a beautifully restored farmhouse and cottage- both exclusively for you during your stay. The property is surrounded by farmland and forest providing complete privacy and tranquility, yet the nearest village is only 3kms away. The property comfortably sleeps up to 12 people and has a large salt water filtered swimming pool. Fabulous restaurants, wineries and stunning Tuscan & Umbrian villages are but a short drive. Welcome.

A charming stone building features a sloped tiled roof and wooden beams. Tall cypress trees rise beside the structure, which is surrounded by lush greenery and vibrant flower pots. Stone steps lead to the entrance, creating an inviting outdoor setting.

4.98 out of 5 average rating, 44 reviews

The Castellaccio of Figline

L'alloggio si trova al PRIMO PIANO di una villa immersa nel verde denominata “Il Castellaccio”, che deve il suo nome alla vicinanza con le rovine del vecchio castello appartenuto alla famiglia degli Uberti. La casa gode di una magnifica vista sulla campagna circostante ed è ideale per una vacanza rilassante per famiglie o gruppi di amici, con la possibilità di visitare città d’arte e godere degli splendidi paesaggi del Chianti, nonché delle specialità enogastronomiche della zona.

Top guest favorite

Home

4.98 out of 5 average rating, 130 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

4.82 out of 5 average rating, 57 reviews

Two elegant glasses of red wine are placed on a dark wooden table, accompanied by a loaf of freshly sliced bread on a wooden board. A panoramic view of rolling hills and greenery stretches in the background, under a partly cloudy sky.

Apartment

"La Sartina" Vacation Home

Beautiful newly renovated house (2023) with a beautiful view of the Ombrone Valley, where you can admire a beautiful sunrise and appreciate the wonderful Tuscan Maremma. Excellent finishes, 4 beds, air conditioning, very central to the typical Tuscan village of Sasso D'Ombrone. 100 meters from the Bar/Market/Emporio, the post office and the bus stop. 1500m from Albus Alpacas (Alpaca Experience). Serious and helpful owner.

A serene swimming pool area is framed by lounge chairs and shaded by a large umbrella. The crystal-clear pool reflects the sky, surrounded by manicured greenery and tall cypress trees. Rolling hills and distant landscapes provide a scenic backdrop, enhancing the outdoor escape.

5 out of 5 average rating, 32 reviews

Vakantievilla Farmhouse Dolci Hills

This luxurious villa (casale) is located near the village of Allerona on the border of Tuscany and Umbria and is 15 km from Orvieto, 100 km from Rome and 120 km from Florence. Casale Colline Dolci is perfect for guests who want to enjoy in all comfort and tranquility the beauty of the Italian countryside and its excellent cuisine, but equally ideal for those who want to soak up the beautiful culture of Italy.

The image depicts a panoramic view of a tranquil landscape featuring a private swimming pool surrounded by sun loungers. The rolling hills of the Valdarno valley stretch into the distance, dotted with olive trees, while a charming farmhouse is visible on the hillside.

4.91 out of 5 average rating, 23 reviews

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.

4.93 out of 5 average rating, 107 reviews

The historic skyline of San Gimignano is visible against a clear blue sky. The image showcases a collection of medieval towers and buildings set atop gently rolling hills, surrounded by patches of lush greenery and olive trees.

Apartment

"Il Nespolo" Apartment - Girasole Location

The apartment "Il Nespolo", location "Girasole", is located in the historic center of San Gimignano, just 150 meters from Piazza del Duomo, in a side street of the main street. The property is in the immediate vicinity of all points of interest and at the same time away from the noise of the busiest street in the town.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Montalcino vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Montalcino's top sights

Valdorcia6 locals recommend

Murlo25 locals recommend

Centro Benessere Le Terme6 locals recommend

Montalcino Fortezza station16 locals recommend

Pienza Cathedral3 locals recommend

Coop12 locals recommend

Other great vacation rentals in Montalcino

Apartment in Mercatale Valdarno

A private outdoor space features a serene swimming pool surrounded by stone tiles. Comfortable lounge chairs are positioned near the pool. A gazebo provides shade, furnished with seating, and overlooks lush greenery, enhancing the tranquil atmosphere of the area.

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

4.9 out of 5 average rating, 179 reviews

A charming stone exterior features large windows and arched details, surrounded by lush greenery. A path lined with lavender leads to the entrance, with outdoor seating visible under shaded umbrellas. The tranquil setting is complemented by nearby trees and rolling hills in the background.

Cottage in Volterra

Podere Grignano, beautiful Tuscany

5 out of 5 average rating, 7 reviews

A spacious outdoor area is showcased, featuring a shared swimming pool surrounded by well-maintained lawns and sun loungers. Umbrellas provide shaded seating, while the scenic countryside extends in the background, enhancing the tranquil ambiance of the agriturismo.

Farm stay in Camucia

The Garden of Olives | Casa Ippocastano

4.94 out of 5 average rating, 18 reviews

A serene outdoor loggia features stone arches framing two potted flowering plants with vibrant purple blooms. The rustic wooden table is located nearby, and a lush garden with trees and greenery can be seen in the background, contributing to a calm atmosphere.

Villa in Radicondoli

A Romantic Villa in the heart of Tuscany

4.95 out of 5 average rating, 75 reviews

A covered loggia is framed by arched brick columns, providing views of a landscaped garden with tall, slender cypress trees. A gravel pathway leads into the distance, inviting exploration of the scenic countryside. Soft clouds drift across a blue sky, contributing to the serene atmosphere.

Villa in Asciano

Podere on the Crete Senesi

4.78 out of 5 average rating, 32 reviews

A well-maintained outdoor swimming pool is surrounded by green grass and shade-providing umbrellas. Lounge chairs are arranged around the pool, offering views of the rolling Tuscan hills and a bright blue sky dotted with clouds.

Cottage in San Gimignano

Glicine romantic cottage in country

4.5 out of 5 average rating, 4 reviews

A rustic dining area features terracotta tile flooring and exposed wooden beams overhead. Large windows frame views of the surrounding landscape. Wooden furniture, including a table and chairs, complement various decorative elements, such as wall art and plants, contributing to a warm, inviting atmosphere.

Apartment in Arezzo

Pozzale Apartment 2+2 | 50m