Condo vacation rentals in Siena

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.

ValueFamilyOutdoor spaces

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

Apartment with independent heating and entrance, renovated , furnished with great care, located in the old part of the city. It features 2 computer friendly zones and allows you to stay with every kind of comfort, including a fitness area. Immersed in the enchantment of the traditional but silent atmosphere of a district of the historic center, it is 50 meters from the Main Street, and from all kinds of shops: restaurants, supermarkets, laundries, newspapers and tobacconists, pastry shops, etc.

ValueLocationLaundry

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, 254 reviews

Palazzo del Taja-in pieno centro con idromassaggio

Appartamento nuovissimo appena ristrutturato, situato all'interno dello storico Palazzo del Taja nel cuore del centro storico di Siena, a pochissimi metri da Piazza del Campo e dalle principali attrazioni della città. Sottoposto ad una ristrutturazione attenta ai dettagli, l'appartamento risulta essere elegante, luminoso, accogliente e silenzioso. Completo di ogni comfort, tra cui una stupenda sala da bagno con vasca idromassaggio, per offrire un soggiorno indimenticabile ai nostri clienti.

ValueFamilyIndoor spaces

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, 196 reviews

Panoramic attic in old town of Siena

We are pleased to propose a top floor apartment in a historic building located in front of the Cathedral of San Domenico, in the heart of the historic center of Siena, a few steps from Piazza del Campo and the Duomo. The area is equipped with every service: shops, cafes, bars, restaurants. Composed of a large living room, kitchen, two double bedrooms, bathroom and terrace with panoramic views of the city. Very bright, it is equipped with every service to make your holiday enjoyable

FamilyLocationOutdoor spaces

A spacious living area features large glass doors leading to a terrace. Furnishings include a white armchair and a wooden coffee table. Outside, a small dining set is visible, offering a scenic view of the city and the Torre del Mangia.

4.91 out of 5 average rating, 152 reviews

"The Terrace" with a awesome Siena skyline

Experience luxury in the heart of Siena at La Terrazza sul Duomo, a stunning apartment located on the third floor of an ancient building. With its prime location and breathtaking terrace, you’ll enjoy unparalleled views of the Torre del Mangia, the Duomo, and San Domenico. Portions of the original exposed stone walls immerse you in the medieval charm of the city. Features: -Three spacious Double Bedrooms -Two Bathrooms fully equipped - Fully Equipped Kitchen - Splendid Living Room

ValueFamilyTV

The open-plan living area is illuminated by natural light from the large windows, featuring a dining table surrounded by four chairs. Elegant wooden beams adorn the ceiling. A modern kitchen with sleek cabinetry and a comfortable seating area is presented, creating a functional and inviting space.

4.94 out of 5 average rating, 192 reviews

Charming apartment in the heart of Siena

The apartment is located in historic centre of Siena, in one of the fascinating streets which leads directly to the main square Piazza del Campo. Strategic location of the apartment makes it an ideal starting point for exploring Siena and it's surroundings, perfect as for single travellers and couples, as for families with kids. In the day of Palio from the windows of the apartment you can enjoy watching historical parade when passing by before entering in Piazza del Campo

ValueLocationWifi

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

Il Chiostro is a characteristic apartment located in the heart of the center of Siena, part of a historic Sienese building dating back to the 1200s! Most appreciated features: ★ Super central location ★ ★ Unique historic architecture ★ ★ Peaceful and quiet environment ★ ★ Very large spaces ★ An excellent solution for those who want to fully experience the city, immerse themselves in its incredible historical atmosphere and enjoy the Tuscan flavor of a unique holiday!

FamilyValueAir conditioning

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

FamilyLocationSleep quality

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, 226 reviews

La porta Accanto 2.0

Grazioso appartamento in stile rustico. Si trova nel centro storico di Siena in una posizione perfetta per visitare a piedi tutti i siti storici, le attrazioni e la zona dello shopping di Siena. In cinque minuti è possibile raggiungere la Piazza del Duomo con il suo museo e la Cattedrale "Santa Maria Assunta". A 600 meti é possibile raggiungere l'incantevole Piazza del Campo dove il 2 luglio e il 16 agosto si svolge il "Palio", la tradizionale corsa di cavalli.

LocationFamilyAir conditioning

5.0 out of 5 average rating, 115 reviews

Lady Camollia Apartment - historic center of Siena

Stay in the heart of Siena's historic center, within the ancient medieval walls, in an elegant 100 m² tourist apartment with external private parking. Just a few steps from Piazza del Campo and the main attractions, it is the ideal solution for families and groups of friends. Typical restaurants, local shops. Comfort, space, and a strategic location for enjoying a true vacation in Siena, surrounded by art, culture, and food and wine.

LocationFamilyParking

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, 122 reviews

NUOVO a Siena, Porta Ovile + free private parking

Goditi una vacanza all'insegna dello stile in questo spazio a due passi dal centro di Siena. Appartamento appena ristrutturato, arredato con cura ed eleganza. Dotato di tutti i comfort è il luogo ideale per chi soggiorna per lavoro o per chi vuole visitare una delle città più belle della Toscana.

ValueLocationBiking

A gravel path meanders through a lush garden, surrounded by vibrant greenery and clusters of flowering plants. Towering trees provide dappled sunlight, enhancing the natural beauty of the serene environment.

4.85 out of 5 average rating, 131 reviews

rare large private garden right in Siena centre

truly central, in the heart of walled city, very easy walking distance to all sites as well as restaurants and shops, but facing away from traffic and onto gardens. great for groups/families/children/longer stays/workation - 3 bedrooms + large living/fourth bedroom

LocationValueOutdoor spaces

Popular amenities for Siena condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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

FamilyLocationBiking

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, 251 reviews

[NUOVO] Moderno Monolocale Centrale con posto auto

FamilyValueCheckout

An open living area features a round dining table surrounded by wooden chairs, and a cozy sofa adorned with decorative cushions. Exposed wooden beams run overhead, adding character to the space. A soft rug enhances the warmth of the wooden flooring, creating a welcoming atmosphere.

4.97 out of 5 average rating, 164 reviews

APPARTAMENTO ROMANTICO NEL CENTRO STORICO DI SIENA

LocationFamilyParking

4.83 out of 5 average rating, 592 reviews

My home in the centre of the city 1

FamilyValueBreakfast

5.0 out of 5 average rating, 161 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

LocationValueWifi

A bright bedroom features a spacious bed adorned with a grey blanket and decorative pillows. Natural light enters through two large windows with sheer curtains, illuminating the room. Exposed brick walls and a wooden beam add character, while a cozy chair is positioned in one corner.

4.96 out of 5 average rating, 186 reviews

Elegant and Bright Central Loft

ValueFamilyAmenities

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

FamilyValueDecor

4.93 out of 5 average rating, 196 reviews

A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.

Condo in Casole d'Elsa

La Casetta

FamilyLocationGetting around

Pet-friendly condo rentals

Condo in Bivio Santo Stefano

A dining area is present, featuring a wooden table surrounded by four chairs. A sideboard is positioned against the wall, displaying glassware. A patterned sofa is located near the entrance, while a small potted plant adds a touch of greenery to the corner.

4.99 out of 5 average rating, 149 reviews

Agriturismo Osea, Sunset flat

FamilyLocationSleep quality

4.97 out of 5 average rating, 344 reviews

A panoramic terrace is depicted, featuring two rattan chairs and a small round table. A pitcher and cups are placed on the table, with vibrant flowers adorning the railing. A clear sky and rolling hills are visible in the background, enhancing the serene outdoor setting.

Condo in Montepulciano

Residenza In cerca d'Autore

FamilyLocationLaundry

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

LocationFamilyLong stay

4.92 out of 5 average rating, 187 reviews

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.

Condo in Montepulciano

Amazing Apartment near Piazza Grande w/ Terrace

ValueLocationAccuracy

4.94 out of 5 average rating, 162 reviews

A wooden dining table is positioned on a shaded patio, featuring a decorative pine cone sculpture at its center. Surrounding greenery includes blooming flowers, with distant hills visible in the background, creating a peaceful outdoor setting ideal for al fresco dining.

Condo in Scandicci

Florentine Hills "Le Scalette"

LocationValueIndoor spaces

4.82 out of 5 average rating, 170 reviews

Lovely Flat in the center of Siena

LocationValueShared spaces

4.95 out of 5 average rating, 181 reviews

Condo in Arezzo

Chianti, elegant barn among vineyards and pool

ValueFamilyShared spaces

Condo in Colle di Val d'Elsa

A dining area is visible, featuring a round table with a fruit bowl containing pears, an orange, and a decorative plant with pink flowers. A vintage lamp stands on a side table, while patterned tiles adorn the walls, creating an inviting atmosphere.

4.92 out of 5 average rating, 272 reviews

Sotto la torre di Arnolfo

ValueLocationParks

Condo rentals with a pool

Condo in Panzano in Chianti

4.96 out of 5 average rating, 281 reviews

Apt.Panzanello-Panzano in Chianti

ValueLocationSleep quality

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

LocationValueQuiet

4.88 out of 5 average rating, 100 reviews

A spacious outdoor swimming pool is surrounded by sun loungers, with umbrellas for shade. Lush greenery and rolling hills can be seen in the background, creating a serene atmosphere. The clear blue water reflects the cloudless sky, inviting relaxation.

Condo in San Gimignano

Charming Tuscan home with pool, garden & Air-Con

ValueFamilyIndoor spaces

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

ValueLocationSleep quality

4.88 out of 5 average rating, 136 reviews

Condo in San Gimignano

Scenic Stilish Country

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 121 reviews

The exterior of the apartment features a spacious garden with a wooden deck and an elevated pool. A stone pathway leads to the entrance. The structure is surrounded by lush greenery and traditional Tuscan buildings, creating a serene environment.

Condo in Castiglioni

[Ninfea] Ancient House in Tuscany

ValueFamilyParking

4.74 out of 5 average rating, 277 reviews

The image depicts a tranquil pool area surrounded by vibrant blooming flowers in pink shades. Poolside loungers are positioned beside an umbrella, with olive trees and green landscaping visible in the background, creating a serene outdoor space.

Condo in Poggibonsi

PODERE VAL DI GALLO CHIANTI SIENA

ValueLocationIndoor spaces

A serene pool area showcases a sparkling water surface under a wide sky. Sun loungers and large umbrellas provide shade for relaxation. The surrounding greenery complements the peaceful landscape, which includes distant hills and rustic buildings.