Condo vacation rentals in Montepulciano

5 out of 5 average rating, 105 reviews

The exterior of a renovated stone house is framed by greenery, featuring large wooden doors that provide a welcoming entrance. An outdoor dining set is visible on the patio, surrounded by carefully maintained gardens and trees, evoking a serene countryside atmosphere.

Condo in Cinigiano

Appartamento Spinosa a Podere Capraia

App.to di due locali su due piani, recentemente ristrutturato con arredamento di buon gusto: soggiorno con divano letto (1 piazza e mezza), tavolo da pranzo, TV, WiFi. Angolo cottura con forno , frigo e lavastoviglie. Bagno con doccia, Wc, bidet. Piano superiore camera matrimoniale mansardata, aperta. Uscita su patio antistante attrezzata. Riscaldamento (dal 15/10 al 15/04) , zanzariere. Ammessi animali piccola media taglia. Piscina ( aperta dal 01/06 al 30/09) condivisa con appartamento Solengo

4.98 out of 5 average rating, 196 reviews

A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.

Condo in Cortona

Chicca: luminosa e panoramica nel centro storico

Luminoso, delizioso e accogliente appartamento situato proprio nel cuore del centro storico di Cortona con un panorama indimenticabile: il palazzo comunale da una parte ed il lago Trasimeno e la Valdichiana dall'altra. L'appartamento è stato recentemente ristrutturato ed è composto da una sala con divano letto, una piccola cucina, una camera matrimoniale e due bagni. Nell'appartamento è disponibile WiFi, riscaldamento ed aria condizionata, lavatrice, forno, microonde, asciugacapelli e piastra.

5 out of 5 average rating, 299 reviews

An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.

Condo in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

5 out of 5 average rating, 136 reviews

A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.

Condo in Pienza

Mascagni Farmhouse in Val d'Orcia Pienza

Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

4.92 out of 5 average rating, 177 reviews

Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.

Condo in Asciano

Appartamento Loggiato 3 in toscana vicino Siena

L'appartamento Loggiato 3 per 2 persone si trova nell'agriturismo Santa Lucia (AGRITURISMO DIVISO IN 7 APPARTAMENTI) nelle Crete Senesi vicino Siena ed è situato al primo piano con tavolino privato dinanzi alle vetrate del loggiato. Composto da camera matrimoniale (due letti singoli uniti), bagno e soggiorno con cucina funzionale. E’ dotato di stufa a legna. Spazio esterno con tavolo e sedie a disposizione al piano terreno. L'ARIA CONDIZIONATA in camera è A PAGAMENTO secondo il consumo.

Condo in Castelfranco di Sopra

A serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.

4.84 out of 5 average rating, 276 reviews

House between Firenze, Arezzo, chianti e Siena

The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

4.97 out of 5 average rating, 321 reviews

An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.

Condo in Asciano

Verde - I prati in Toscana

Appartamento composto da 1 camera matrimoniale , cucina attrezzata, ampio soggiorno e bagno Tv, BBq, ( mettiamo a disposizione la lavatrice dalle 9 alle 20 che è nella nostra lavanderia a chi ne fa richiesta ) . Consigliamo l'auto in quanto abitiamo in campagna, sia per essere indipendenti , sia per visitare la magnifica toscana Ti piacerá l'ambiente esterno perché é magico di giorno e di notte Parcheggio e wifi gratis Posizione strategica per visitare la Toscana e l'Umbria.

A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.

4.92 out of 5 average rating, 154 reviews

"Dimora Valinda" Montepulciano Piazza Grande +A/C

Welcome to Montepulciano, a historical gem! Our apartment, located in the heart of the historic center, offers the perfect location to experience the authenticity of this unique place: just a few steps from Piazza Grande, excellent restaurants, shops, and all the main attractions. Whether you come to explore the wineries, for a romantic getaway, or to learn about the history and culture of Montepulciano, here you will find the perfect place for an unforgettable experience.

4.98 out of 5 average rating, 130 reviews

A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.

Condo in Montalcino

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.

4.91 out of 5 average rating, 131 reviews

A spacious living area features a large window with elegant curtains, allowing natural light to illuminate the room. A comfortable sofa adorned with a cozy blanket is positioned facing a wooden coffee table, while a television and decorative elements add to the ambiance.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Condo in Castelnuovo dell’Abate

A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.

4.91 out of 5 average rating, 306 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.

A terracotta-tiled terrace overlooks rolling hills, adorned with potted plants and a decorative wall. Wooden loungers provide seating, while a small table is positioned under a large tree, offering a shaded spot to enjoy the scenic views of the surrounding landscape.

4.88 out of 5 average rating, 103 reviews

Vicolo delle Mura, ancient home with a view

Our old family home is in a quiet and secluded location in the historic center of Montepulciano. It has a beautiful and large habitable terrace overlooking the Valdichiana. Its central location allows you to walk to Piazza Grande, the Pulcinella Tower, the Medici Fortress and the San Biagio Rectory. Nearby you will find a wide selection of businesses and restaurants where you can enjoy delicious Tuscan cuisine.

Popular amenities for Montepulciano condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A modern kitchen area features a sleek counter with three wooden stools. Hanging light fixtures provide subtle illumination, highlighting the black cabinetry and open shelving displaying dishware. A stainless steel sink is positioned next to an electric kettle, contributing to the functional and inviting design.

4.96 out of 5 average rating, 47 reviews

Milipano Studio Apt

5 out of 5 average rating, 29 reviews

A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.

Condo in San Gimignano

AnticaVista, Luxury Apartment with Tower Views

Superhost

An aerial view captures the property, featuring two rustic buildings surrounded by lush greenery and trees. The inviting infinity pool is clearly visible, reflecting the sky. Rolling hills and vineyards extend in the background, creating a serene and scenic landscape.

Condo in Pienza

4.79 out of 5 average rating, 34 reviews

Poggio ai Gelsi, Lodge Ulivo

A living area is highlighted by a high, intricately detailed ceiling and natural light filtering through a window. A dining table with chairs sits beside a well-equipped kitchen featuring modern appliances. A small seating area includes a TV and a table, complemented by a soft area rug.

4.95 out of 5 average rating, 56 reviews

Sobrio e spazioso appartamento in palazzo Bucelli

The living area features a light-colored sofa and an armchair accented with stripes, alongside a wooden coffee table. A cozy dining table is set against the wall, illuminated by a warm hanging lamp. Large windows provide natural light and views of the outside.

4.95 out of 5 average rating, 64 reviews

Appartamenti al Poggiolo - Borgo - Montepulciano

Condo in Monte San Savino

An aerial view captures the rural estate, showcasing a well-maintained lawn surrounded by lush vineyards. A private pool is visible, complemented by red umbrellas and lounge chairs. The rustic buildings reflect traditional architecture, while trees provide natural shade across the property.

4.96 out of 5 average rating, 71 reviews

La Foresteria | Casa Granaio

A charming corner of a historic building is visible, featuring a textured brick façade and green shutters. Lush vegetation climbs along the side, while terracotta pots add warmth. The narrow, cobblestone street invites exploration, with clear sky overhead and hints of the surrounding landscape in the distance.

4.96 out of 5 average rating, 51 reviews

Ciliano 16

The sleeping area features an elegant bed with light linens, complemented by a rich wooden floor. Exposed brick arches and beams create a warm ambiance. A small desk and lamp are present, along with soft lighting that enhances the historical character of the space.

4.99 out of 5 average rating, 77 reviews

a.d. 1237

Pet-friendly condo rentals

Condo in Tuoro sul Trasimeno

A rustic kitchen is showcased with a stone countertop and a gas stove. Natural light streams through the open window, illuminating items on the shelves, including potted herbs and kitchenware. A microwave sits on the counter, complemented by a bowl of fresh produce.

5 out of 5 average rating, 14 reviews

La Loggia, appartamento in agriturismo

4.94 out of 5 average rating, 133 reviews

A panoramic view showcases rolling hills covered with vineyards under a clear blue sky. Lush greenery is visible in the foreground, with vibrant plants framing the landscape, creating a serene backdrop of the Tuscan countryside.

Condo in Panzano

Appartamento con vista a Panzano in Chianti

Superhost

An aerial view captures a historic Tuscan village with rustic stone buildings and terracotta roofs. Lush greenery surrounds the courtyard, and a tower stands prominently among carefully arranged gardens and pathways, providing a sense of tranquility amidst scenic landscapes.

Condo in Montefollonico

4.88 out of 5 average rating, 34 reviews

Appartamento con giardino panoramico, Valdorcia

4.97 out of 5 average rating, 197 reviews

A view captures a historic building in Siena, displaying its rustic architecture and multiple arched windows. In the foreground, trees bloom with pink flowers, while green vegetation adds a touch of nature. The iconic tower of Siena is visible in the background under a clear blue sky.

Condo in Siena

La porta Accanto 2.0

4.97 out of 5 average rating, 149 reviews

A quaint kitchen and living area is captured, showcasing exposed wooden beams and terracotta flooring. A cozy sofa with floral upholstery complements a wooden dining table set with various dishes and fresh flowers. Natural light floods in through the windows, creating a warm atmosphere.

Condo in Cortona

Casa Clara Cortona Cin IT051017c28a6h9glv

4.96 out of 5 average rating, 180 reviews

An open dining area features a wooden table surrounded by white upholstered chairs. A large window allows natural light to fill the space, highlighting plants in decorative pots. The room is adorned with artwork and has a comfortable seating area in the background.

Condo in Siena

Elegant fine home 400 m away from Piazza del Campo

4.89 out of 5 average rating, 174 reviews

A spacious balcony is lined with arches, providing a panoramic view of the rooftops and distant cathedral of Siena. Terracotta tiles cover the floor, while potted plants add a touch of greenery. Sunlight floods the area, enhancing the architectural features and scenic outlook.

Condo in Siena

Panoramic attic in old town of Siena

4.93 out of 5 average rating, 136 reviews

A rustic rural complex is depicted, featuring a stone building with a terracotta roof. Surrounding greenery enhances the setting, and a gravel path leads to the entrance. The scene is accentuated by a large tree and the clear sky above.

Condo in Monteriggioni

Il Vecchio Noce

Condo rentals with a pool

4.88 out of 5 average rating, 164 reviews

A small outdoor table is set for two on a private terrace, featuring a mosaic surface. Two glasses of red wine and a plate of snacks sit on the table. The view includes rolling hills, olive trees, and distant homes, creating a serene countryside backdrop.

Condo in Cavriglia

Chianti La Pruneta, Michelangelo apartment

5 out of 5 average rating, 39 reviews

An aerial view captures a green landscape featuring a private pool surrounded by lounge chairs. Stone paths meander through manicured gardens, leading to a rustic cottage nestled among tall cypress trees. The serene setting emphasizes privacy and relaxation.

Condo in Buonconvento

Cottage 48 mq, piscina, relax, immerso nel verde

4.91 out of 5 average rating, 33 reviews

An aerial view captures the expansive outdoor area, featuring a large swimming pool surrounded by sun loungers and parasols. Lush greenery and neatly trimmed hedges complement the rustic stone buildings, while pathways lead to various areas of the property.

Condo in Cortona

Fattoria Borgonuovo - L'Ortensia

Condo in Castellina in Chianti

A wooden dining table is set in a grassy area, surrounded by tall trees and stone walls. Six folding chairs are positioned around the table, which holds a bottle of wine and several plates. The scene is framed by lush greenery, suggesting a serene outdoor dining experience.

4.96 out of 5 average rating, 52 reviews

Il Giaggiolo - Chianti with a view

4.87 out of 5 average rating, 78 reviews

A spacious living area features a wooden dining table surrounded by woven chairs, complemented by a cozy atmosphere provided by wooden beams overhead. Large doors open to the outdoor space, with natural light illuminating the terracotta flooring and decorative elements in the background.

Condo in Pienza

Guidoccio-Agriturismo Cosona

An outdoor swimming pool is featured, surrounded by lush greenery and trees. Poolside lounge chairs and an umbrella provide relaxation options. Soft lighting creates a serene atmosphere as dusk falls over the charming countryside, with a rustic building visible in the background.

4.88 out of 5 average rating, 49 reviews

Appartamento Girasole