Condo vacation rentals in Montepulciano

4.98 out of 5 average rating, 223 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: centro storico di Cortona

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.

LocationFamilyHeating

5.0 out of 5 average rating, 350 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 proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

FamilyValueCondition

A charming terrace features a small round table and two white chairs, offering expansive views of the surrounding hills and distant landscape. A walnut tree stands nearby, enhancing the tranquil outdoor space bathed in natural light from the setting sun.

5.0 out of 5 average rating, 136 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

ValueLocationIndoor spaces

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, 187 reviews

Amazing Apartment near Piazza Grande w/ Terrace

Benvenuti nel cuore di Montepulciano, uno dei borghi più iconici, affascinanti e storici della Toscana, celebre per i suoi palazzi rinascimentali, le antiche cantine e l’atmosfera senza tempo che conquista ogni viaggiatore. Il nostro appartamento si trova in una posizione incredible nel pieno centro storico, a pochi passi da Piazza Grande, ottimi ristoranti, botteghe locali e dalle meraviglie più autentiche del paese. Che siate qui per degustare vini straordinari, vivere una fuga romantica.

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 160 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

Casa rurale toscana in Mascagni Farmhouse 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?

LocationFamilyBiking

4.97 out of 5 average rating, 317 reviews

A spacious bedroom features warm brick walls and a wooden beamed ceiling. A large bed with a striped blanket is positioned next to a cozy seating area. A desk and chair setup is visible, along with a Smart TV mounted above, completing the functional space.

Condo in Torrenieri

[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.

LocationFamilyAmenities

4.98 out of 5 average rating, 324 reviews

Aerial view of a charming countryside villa surrounded by rolling hills and vineyards. Olive trees are visible lining the roads, which lead to the home nestled within a serene natural landscape. The colors and textures reflect the characteristic beauty of the Tuscan countryside.

Condo in Asciano

Celeste - Il colore del cielo d'estate in Toscana

Appartamento si trova al 1 piano composto da 2 camere (possibilità di fare letti singoli o matrimoniali a richiesta ) bagno, soggiorno, cucina attrezzata per cucinare . ( lavatrice a disposizione dalle 9 alle 20 nella lavanderia ) Parcheggio e wifi gratuiti Posizione strategica per visitare i centri turistici della Toscana. Noi siamo in campagna , nel cuore delle Crete Senesi , è consigliata l'auto per essere indipendenti e visitare la magnifica campagna toscana

ValueLocationLong stay

The living area features a combination of a soft beige sofa set and two armchairs, arranged around a small round table. A traditional area rug enhances the space, while a stone wall adds texture. A flat-screen television is mounted on the wall near a low cabinet.

4.94 out of 5 average rating, 218 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.

ValueLocationCondition

4.92 out of 5 average rating, 147 reviews

A cozy bedroom features a spacious bed with neutral-toned linens and decorative pillows. The warm yellow walls are adorned with framed photographs, while shelves hold books and small decorative items. Soft lighting enhances the inviting atmosphere, creating a comfortable space for relaxation.

Condo in Pienza

Casa Gioia

Il mio alloggio è situato nel centro storico di Pienza, al secondo piano senza ascensore. Affaccia sul corso principale di Pienza. I parcheggi più vicini a pagamento distano 150m, quelli liberi 300m, zona carico/scarico 50m. Ti piacerà il mio alloggio per questi motivi: la comodità del letto, l'intimità, i soffitti in travi in legno e cotto tipico nel pavimento. Il mio alloggio è adatto a coppie, chi viaggia per lavoro e famiglie (con bambini)

LocationFamilyWifi

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.

4.9 out of 5 average rating, 324 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.

FamilyLocationQuiet

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.

4.86 out of 5 average rating, 111 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.

ValueLocationComfort

4.96 out of 5 average rating, 161 reviews

An outdoor terrace features a glass dining table set for four, complemented by green chairs. A bottle of wine and glasses rest on the table, with vibrant red flowers adding a pop of color. A scenic valley view showcases rolling hills and a distant mountain.

Condo in Chiusi

La Terrazza su Chiusi - appartamento panoramico

Ampio e spazioso appartamento nel centro storico, confortevole, ben rifinito, comodo salone e grande terrazzo dotato di barbecue. Attrezzato di ogni elettrodomestico, ben ventilato, perfetto per soggiorni rilassanti, vicino e ben collegato alle più conosciute mete turistiche come Siena, Roma, Firenze, Perugia, Arezzo e altre.

LocationValueOutdoor spaces

Popular amenities for Montepulciano condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.95 out of 5 average rating, 143 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"

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A modern bedroom features a spacious bed with soft linens against a stylish mural of an arched window adorned with greenery. A vintage-style mirror complements the elegant decor, while soft lighting highlights the architectural details of the brick archway.

5.0 out of 5 average rating, 121 reviews

NUOVO a Siena, Porta Ovile + free private parking

LocationValueQuiet

Condo in San Quirico d'Orcia

A modern living area features two comfortable sofas and a wooden coffee table. Soft lighting enhances the space, complemented by decorative wall art. A television is positioned against a minimalist entertainment unit, with natural light filtering through sheer curtains.

4.93 out of 5 average rating, 114 reviews

RESIDENCE HILL

FamilyLocationCondition

Condo in Tuoro sul Trasimeno

A spacious living area is adorned with a vintage-style sofa and a decorative wooden armchair. Natural light floods the space through large windows covered with light curtains. A brick fireplace adds warmth, and a patterned rug enhances the room's character.

4.97 out of 5 average rating, 118 reviews

L'Appartamento di Foscolo

FamilyLocationLong stay

4.99 out of 5 average rating, 313 reviews

An aerial view reveals the historic village of San Donato in Poggio, showcasing charming medieval architecture and surrounding hills. The apartment is distinguished by its stone façade, nestled among lush greenery and olive trees, with terracotta rooftops complementing the landscape.

Condo in San Donato

Old medieval apartment

ValueFamilyTV

Condo in Castiglione del Lago

The bedroom features a wrought iron bed adorned with an orange coverlet. A wooden desk and chair are positioned beside a round mirror, providing a functional space. Natural light filters through the window, while rustic walls and high ceilings enhance the classic charm of the room.

4.95 out of 5 average rating, 219 reviews

AURA Garbino appartamento in centro storico

FamilyLocationCondition

A modern living space features a bright red sectional sofa positioned against a textured stone wall. A stylish kitchen island with seating is visible, along with minimalistic lighting fixtures and decorative plants, creating a blend of comfort and contemporary design.

4.99 out of 5 average rating, 253 reviews

Palazzo del Taja-in pieno centro con idromassaggio

ValueLocationSleep quality

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.

4.98 out of 5 average rating, 86 reviews

a.d. 1237

ValueFamilyLaundry

Pet-friendly condo rentals

Superhost

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.

Condo in Castelfranco di Sopra

4.84 out of 5 average rating, 300 reviews

House between Firenze, Arezzo, chianti e Siena

ValueLocationHiking

Condo in Castiglione d'Orcia

4.92 out of 5 average rating, 214 reviews

Ermione

ValueLocationSleep quality

An open living space showcases a white sofa adorned with orange and patterned cushions. Green accent chairs complement the decor. A wooden coffee table sits in the center, while a staircase ascends to a brighter upper level, highlighted by warm lighting and framed artworks.

4.96 out of 5 average rating, 188 reviews

Vintage apartment 400m PalioPiazza del Campo Siena

ValueLocationLaundry

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.

4.97 out of 5 average rating, 224 reviews

La porta Accanto 2.0

FamilyLocationGetting around

Superhost

The living area features exposed brick walls and a wooden beam ceiling. A white leather couch and a dark leather armchair are positioned around a glass coffee table. A decorative folding screen with floral patterns stands in the corner, while a large mirror reflects the bright space.

4.89 out of 5 average rating, 123 reviews

•Il Chiostro• Una chicca nel cuore di Siena

LocationValueAccess

A spacious living area features a comfortable seating arrangement, with light-colored sofas and decorative pillows. A wooden coffee table sits on a vibrant area rug, while sunlight filters through sheer curtains. Wall art and a large television enhance the inviting atmosphere.

4.99 out of 5 average rating, 102 reviews

Casa Manori - raffinato e accogliente bilocale

LocationFamilyKitchen

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.

4.89 out of 5 average rating, 195 reviews

Panoramic attic in old town of Siena

ValueLocationParks

The modern living area features a sleek gray sofa, positioned beneath large windows that allow ample natural light. Local artwork adorns the walls, and a stylish wooden rack is present for hanging clothes. A minimalist lamp contributes to the clean aesthetic.

4.94 out of 5 average rating, 250 reviews

[NUOVO] Moderno Monolocale Centrale con posto auto

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Condo rentals with a pool

Condo in Panzano in Chianti

4.96 out of 5 average rating, 281 reviews

Apt.Panzanello-Panzano in Chianti

FamilyValueCheckout

4.95 out of 5 average rating, 181 reviews

Condo in Arezzo

Chianti, elegant barn among vineyards and pool

LocationValueBeach

Condo in Castellina in Chianti

A shaded outdoor terrace features a rustic wooden table set with wine glasses and a bottle of Chianti, accompanied by a plate of snacks. Lush greenery and tall trees are visible in the background, contributing to a serene countryside view.

4.81 out of 5 average rating, 365 reviews

Relax Tra Le Vigne Del Chianti-IlVillinoFarmhouse

FamilyValueCheckout

4.95 out of 5 average rating, 151 reviews

A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.

Condo in San Gimignano

Adalberto Apartment inside the Manor of Fulignano

FamilyValuePets

4.91 out of 5 average rating, 95 reviews

A warm living space showcases exposed wooden beams and light-colored walls. A staircase leads to an upper level, while a cozy seating area features a light gray sofa. A dining table is positioned near windowed doors that offer views of the surrounding countryside.

Condo in Montefollonico

Tuscan Dream Apt with Pool, View & Tennis Court

FamilyLocationGetting around

Condo in Castelnuovo Berardenga

An aerial view captures a rustic stone building surrounded by lush greenery and tall cypress trees. A sparkling swimming pool is visible in the yard, complemented by sun loungers. Rolling vineyards stretch into the background, enhancing the serene landscape.

4.97 out of 5 average rating, 88 reviews

Charming Residence Castello di Orgiale near Siena

FamilyLocationView

4.95 out of 5 average rating, 19 reviews

A spacious living area features a striped sofa with soft cushions, complemented by a wooden coffee table and a vase of fresh flowers. The warm terracotta flooring and rustic beams enhance the inviting ambiance. Steps lead to additional rooms, visible in the background.

Condo in Montisi

Apartment in ancient house + pool and terrace

LocationFamilyComfort