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Villa holiday rentals in Asciano

Find and book unique villas on Airbnb

Quick stats about villa rentals in Asciano

  • Total holiday rentals

    Explore 70 holiday rentals in Asciano

  • Nightly prices starting at

    Asciano holiday rentals start at $175 NZD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Asciano holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Asciano rentals

  • 4.9 Average rating

    Asciano stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated villa rentals in Asciano

Guests agree: These villas are highly rated for location, cleanliness and more.

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Top Guest favourite
Villa in Chianciano Terme

Charming Tuscan Villa in Val d'Orcia with a view

Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

FamilyLocationLong stay

4.97 out of 5 average rating, 130 reviews
Guest favourite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia

San Giovanni in Poggio, villa Meriggio 95mq

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

LocationFamilyHot tub

4.98 out of 5 average rating, 128 reviews
Top Guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

LocationValueLong stay

4.97 out of 5 average rating, 126 reviews
Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

ValueLocationSleep quality

4.93 out of 5 average rating, 256 reviews
Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

LocationFamilyHospitality

4.9 out of 5 average rating, 240 reviews
Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

FamilyValueHospitality

4.92 out of 5 average rating, 337 reviews
Top Guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

ValueFamilyBiking

4.96 out of 5 average rating, 169 reviews
Top Guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

La Vignaccia (Farmhouse) - villa w/private pool

Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.

FamilyValueCheck-in

4.96 out of 5 average rating, 102 reviews
Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Casale in pietra in Val D’Orcia

Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.

FamilyValueLaundry

4.98 out of 5 average rating, 160 reviews
Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

LocationFamilyCleanliness

4.98 out of 5 average rating, 107 reviews
Top Guest favourite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

FamilyLocationGetting around

4.98 out of 5 average rating, 183 reviews
Top Guest favourite
Villa in Monteroni d'Arbia

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

LocationValueNearby

4.95 out of 5 average rating, 174 reviews

Popular amenities for Asciano villa rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Private villa rentals

Top Guest favourite
The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.
Villa in San Leolino

Poggio del Fattore-Villa with pool,hilltop,Chianti

LocationFamilyKitchen

4.99 out of 5 average rating, 131 reviews
Top Guest favourite
Villa in Arezzo

Tuscany View - Villa Arianna

LocationValueGetting around

4.99 out of 5 average rating, 123 reviews
Guest favourite
Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

FamilyLocationComfort

4.97 out of 5 average rating, 174 reviews
Superhost
The stone exterior of the house is framed by vibrant flowers and lush greenery. A shaded terrace offers seating with views of the surrounding hills. Potted plants add color to the pathway made of large stones, leading to the entrance of the home.
Villa in Radda in Chianti

la Balza

LocationFamilyAccuracy

4.93 out of 5 average rating, 128 reviews
Top Guest favourite
Villa in Montecatini Val di Cecina

Torre dei Belforti

ValueLocationPets

4.99 out of 5 average rating, 138 reviews
Guest favourite
A sparkling pool is set in a well-maintained lawn, surrounded by tall trees and cypress plants. Comfortable lounge chairs are positioned beside the water, with a shaded area provided by an umbrella. The rustic villa can be seen in the background against a clear blue sky.
Villa in Asciano

Podere on the Crete Senesi

FamilyLocationIndoor spaces

4.96 out of 5 average rating, 92 reviews
Superhost
Villa in Asciano

Pieve Di Sant Ippolito - Sant Ippolito

ValueLocationKitchen

5.0 out of 5 average rating, 16 reviews
Guest favourite
Villa in Siena

L'Apparita del Peruzzi | Villa | Private Pool & AC

LocationFamilyLayout

5.0 out of 5 average rating, 22 reviews

Luxury villa rentals

Guest favourite
Villa in Montepulciano

Villa a Montepulciano con Piscina

FamilyValueHospitality

4.92 out of 5 average rating, 148 reviews
Top Guest favourite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

LocationFamilyLaundry

4.98 out of 5 average rating, 120 reviews
Guest favourite
Villa in Castell'In Villa

Villa marielena chianti farmhouse with hot tub - v

LocationFamilyCleanliness

5.0 out of 5 average rating, 10 reviews
Guest favourite
An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.
Villa in Poggibonsi

Villa with pool in Chianti Area

ValueLocationComfort

4.95 out of 5 average rating, 73 reviews
Guest favourite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo

Fabulous Farmhouse with Pool & 360 Panoramic View

LocationFamilyComfort

4.92 out of 5 average rating, 62 reviews
Top Guest favourite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti

Sestuccia

LocationFamilyCheck-in

4.99 out of 5 average rating, 76 reviews
Top Guest favourite
A serene pool area is framed by lush olive trees and a spacious lawn. Two lounge chairs are positioned by the edge of the inviting pool, with the house visible in the background, showcasing its traditional architecture and surrounding greenery.
Villa in Lucignano

Unique Villa in Tuscany

FamilyLocationIndoor spaces

4.93 out of 5 average rating, 42 reviews
Guest favourite
A traditional stone villa is set amidst trees and greenery, showcasing multiple windows framed by wooden shutters. The building features a tiled roof with chimneys and an inviting outdoor area with potted plants. A serene landscape is visible in the background.
Villa in Gaiole in Chianti

Lucignano Secondo - La Villa

FamilyLocationNearby

4.89 out of 5 average rating, 35 reviews

Villa rentals with a pool

Guest favourite
Villa in Badia a Passignano

Guardia di Badia a Passignano

LocationViewAccuracy

4.86 out of 5 average rating, 7 reviews
Guest favourite
Villa in Arezzo

Coaching House

LocationFamilyHospitality

5.0 out of 5 average rating, 67 reviews
Guest favourite
The property features a charming rustic stone house and a secondary building set against a backdrop of bright blue skies and scattered clouds. Lush green grass surrounds the structures, enhancing the natural beauty of this tranquil countryside setting.
Villa in Castiglion Fiorentino

Villa il Laghetto with Infinity Pool in Tuscany

FamilyLocationComfort

4.96 out of 5 average rating, 56 reviews
Superhost
A tranquil swimming pool is framed by sun loungers and umbrellas, offering a refreshing spot to relax. The villa is positioned above, showcasing its classic architecture and landscaped gardens, surrounded by lush greenery and blooming flowers.
Villa in Lucignano

Magnificent 1700's villa in Tuscany

LocationValueLaundry

4.81 out of 5 average rating, 69 reviews
Guest favourite
The rustic stone villa is surrounded by vibrant flower beds and lush greenery. A small ornamental pond with lily pads is featured in the garden. The property showcases multiple levels of terraces adorned with colorful blooms and climbing vines, enhancing the natural beauty of the landscape.
Villa in Lucignano

Sasso Canaldo Charming property in Tuscany

LocationFamilyKitchen

5.0 out of 5 average rating, 6 reviews
Guest favourite
An outdoor dining area is presented under a wooden pergola, featuring a long table set for meals. Soft lighting is provided by hanging fixtures, and the surrounding lush greenery complements the rustic stone structure in the background.
Villa in Lucignano

Villa Eleonora

FamilyLocationCleanliness

4.85 out of 5 average rating, 20 reviews
Guest favourite
A spacious room features a wooden ceiling and green walls, showcasing two cozy armchairs and a small table. Sunlight pours in through a large window, offering views of the surrounding trees. A neatly made bed is positioned in the foreground, with soft towels arranged for convenience.
Villa in Scrofiano

Podere Mencoini beautiful villa with priv pool A/C

LocationFamilyWi-Fi

4.96 out of 5 average rating, 28 reviews
Top Guest favourite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa in Castiglion Fiorentino

Tuscany Villa Mammi

FamilyValueCondition

4.99 out of 5 average rating, 90 reviews

When is the best time to visit Asciano?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$821 NZD$828 NZD$764 NZD$674 NZD$686 NZD$676 NZD$685 NZD$681 NZD$667 NZD$515 NZD$445 NZD$821 NZD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

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