
Condo vacation rentals in Montalcino
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Quick stats about condo rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at G$18,830 GYD per night before taxes and fees

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Over 450 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Montalcino rentals

4.9 Average rating
Montalcino stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated condo rentals in Montalcino
Guests agree: these condos are highly rated for location, cleanliness, and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 352 reviews
Pink like the sunset sky
The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!
4.99 out of 5 average rating, 235 reviews
The walnut tree view, Montepulciano
The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment
5.0 out of 5 average rating, 137 reviews
[9 minutes from Montalcino] Elegant House Mafalda
Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.
4.97 out of 5 average rating, 317 reviews
Amazing Apartment near Piazza Grande w/ Terrace
Welcome to the heart of Montepulciano, one of Tuscany’s most iconic, charming, and historic towns, renowned for its Renaissance palaces, ancient wine cellars, and timeless atmosphere that captivates every traveler. Our apartment is in an incredible location right in the historic center, a short walk from Piazza Grande, excellent restaurants, local shops, and the town's most authentic treasures. Whether you're here to taste extraordinary wines or enjoy a romantic getaway.
4.92 out of 5 average rating, 189 reviews
Suite "Note di Paesaggio"
The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.
4.95 out of 5 average rating, 144 reviews
HOLIDAY APARTMENT IN HISTORICAL PALACE- MARINA
The apartment is located in an historical palace in the very heart of the old town. Near to all monuments, shops and restaurants but extremely quiet and peaceful. The old town is a pedestrian area . The flat is at the second floor. There is a lift for luggage and wheelchairs. From the windows you can enjoy a wonderful view. The apartment has recently been refurbished to a very high standard and furnished with elegance and traditional Tuscan antiques.
4.94 out of 5 average rating, 219 reviews
Tuscan rural home in Mascagni Farmhouse Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?
5.0 out of 5 average rating, 162 reviews
RESIDENCE HILL
Residence Hill is a luxurious apartment suitable for couples but also for families, equipped with 3 bedrooms different in style, a kitchen equipped with all comforts, dishwasher, fan oven, kettle and coffee machine, living room and large living area, 50" LED TV and each Suite equipped with all comforts, double bathrooms with whirlpool tub and shower with massage function, SPA corner with Turkish Bath and relaxation area with herbal tea, free Wi-Fi.
4.92 out of 5 average rating, 117 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.
4.9 out of 5 average rating, 324 reviews
Casa Gioia
My place is located in the historic center of Pienza, on the second floor without an elevator. It overlooks the main street of Pienza. The nearest paid parking lots are 150m away, the free ones 300m, loading/unloading area 50m. You'll love my place because of the comfort of the bed, the intimacy, the wooden-beam ceilings, and the typical terracotta floor. My place is good for couples, business travelers, and families (with kids)
4.92 out of 5 average rating, 149 reviews
Amazing view of Val d'Orcia Pienza
Beautiful 75-square-meter apartment located on the ground floor of the “Podere Colombaio,” a historic farmhouse named after its 15th-century tower. The property features a lovely pergola and a garden overlooking the Val d’Orcia Park, just a 10-minute walk from Pienza.
4.92 out of 5 average rating, 126 reviewsPopular amenities for Montalcino condo rentals
Weekly condo rentals

Chicca: Cortona's historic center
4.98 out of 5 average rating, 223 reviews
Vicolo delle Mura, ancient home with a view
4.86 out of 5 average rating, 111 reviews
NEW in Siena, Porta Ovile + free private parking
5.0 out of 5 average rating, 122 reviews
Panoramic attic in old town of Siena
4.89 out of 5 average rating, 197 reviews
Palazzo del Taja - in the center with whirlpool
4.99 out of 5 average rating, 254 reviews
Chianti, elegant barn among vineyards and pool
4.95 out of 5 average rating, 181 reviews
Old medieval apartment
4.99 out of 5 average rating, 313 reviews
Lady Camollia Apartment - historic center of Siena
5.0 out of 5 average rating, 117 reviewsPet-friendly condo rentals

The Door Next Door 2.0
4.97 out of 5 average rating, 227 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Vintage apartment 400m PalioPiazza del Campo Siena
4.96 out of 5 average rating, 188 reviews
AURA Garbino apartment in the historic center
4.95 out of 5 average rating, 220 reviews
Casa Manori - refined and cozy two-room apartment
4.99 out of 5 average rating, 102 reviews
•Il Chiostro• A gem in the heart of Siena
4.89 out of 5 average rating, 123 reviews
[NEW] Modern Central Studio with parking space
4.94 out of 5 average rating, 253 reviews
Foscolo's Apartment
4.97 out of 5 average rating, 119 reviewsCondo rentals with a pool

La Casetta
4.93 out of 5 average rating, 197 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Relax among the vineyards of Chianti-IlVillinoFarmhouse
4.81 out of 5 average rating, 365 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 96 reviews
Charming Residence Castello di Orgiale near Siena
4.97 out of 5 average rating, 88 reviews
Apartment in ancient house + pool and terrace
4.95 out of 5 average rating, 19 reviews
Romantic cottage in Tuscany with pool and garden
5.0 out of 5 average rating, 58 reviewsDestinations to explore
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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Del Chianti
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- La Scarzuola
- Antinori nel Chianti Classico
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Basilica Di San Miniato A Monte
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Things to do Montalcino
- Things to do Siena
- Art workshops Siena
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- Museums Siena
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- Things to do Tuscany
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- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
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