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Villa holiday rentals in Siena

Find and book unique villas on Airbnb

Top-rated villa rentals in Siena

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

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Villa in Chianciano Terme

5 out of 5 average rating, 10 reviews

3 bdr Lux Villa in Montepulciano Tuscany,Top View

Live your own experience as a local at LaVittoria 10 in Val d'Orcia, short driving to Montepulciano, Pienza, Cortona,Siena Huge apt on top floor of the Villa, with 2 magnificent suites, panoramic lounge and professional kitchen, plus The Cottage,for 2+1 pp, with private entrance, kitchen, large bdr and bathroom with Jacuzzi for 2! Hot tub with top view in the garden and relax area with comfy sofas !Your local host arranges priv dinners and Wineries tour & tasting. Ebikes tour with guide. Wifi

Guest favourite

Villa in Sovicille

5 out of 5 average rating, 13 reviews

Exclusive farmhouse, pool, en-suite A/C rooms

Tuscany Villa with privatepool,max 8 pax, SienaView. Siena only 8km driving; less than 5 minutes driving you have supermkt, pizzeria, bank, restaurants. 2 Floors only for you, about 250 sqm 4 bathrooms en suite, Airconditioning, Private pool and garden NO AREAS SHARED WITH OTHER GUESTS Inside an organic Farm, where you can see the real Farm work, to know Farmers and visit their Organic Pasta factory, to have Farm Experience on demand, purchase and taste our organic products ENJOY YOUR TUSCANY!

Villa in Monsummano Terme

4.82 out of 5 average rating, 50 reviews

Florence & Tuscany. Pool, jacuzzi, parking & relax

Charming 15th century Tuscan Villa, 5bdr, restored respecting local traditions, fenced and furnished with international taste. A 360° view and exclusive comfort. Strategic position -in the heart of Tuscany- 10 minutes from Thermal Spa "Grotta Giusti" and from the motorway, to easily reach Florence, Lucca, Pisa, Siena, beaches & Cinque Terre. Surprising, 30 steps away: you can discover a restaurant of excellence, for unforgettable dinners. We are absolutely certain: it will not disappoint you!

Guest favourite

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 102 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Guest favourite

Villa in Cortona

5 out of 5 average rating, 69 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Villa in Castelnuovo Berardenga

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Guest favourite

Villa in San Casciano

4.97 out of 5 average rating, 105 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Guest favourite

Villa in Barullo-Centoia

4.91 out of 5 average rating, 43 reviews

Bellora: A Perfect Villa in Cortona, Tuscany

Discover the epitome of Tuscan luxury at our exquisite villa, boasting an idyllic location near Cortona. A mere 15-20 minute drive to Cortona and 25 minutes to Montepulciano, it offers unparalleled convenience for exploring Tuscany. Nestled within a private gated estate, this opulent haven showcases 3 bedrooms, 2 pristine bathrooms, and a generously-sized swimming pool exclusively reserved for your indulgence. Youtube: "Villa Bellora Cortona Drone fly by"

Villa in Radicondoli

4.94 out of 5 average rating, 17 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Villa in Montescudaio

4.8 out of 5 average rating, 10 reviews

PRIVATE VILLA BERTI TUSCANY FOREVER Montescudaio

Villa Berti TUSCANY FOREVER. This is standalone, new villa with private swimming pool and 3 bedrooms and 2 bathrooms. WE KNOW WHERE HAPPY KIDS ARE ! TUSCANY FOREVER featuring unique family friendly properties. Berti is located 2km from the center of Montescudaio town with magnificent views. Etruscan coast , the sea is about 10km away. If you’re facing an issue that requires a personal touch, please contact us.

Guest favourite

Villa in Orentano

4.96 out of 5 average rating, 100 reviews

Charming Villa in Stone in Tuscany, Borgo ai Lecci

The location, easily accessible, is perfect for visiting the main attractions in Tuscany: the cities of art, the old villages, beautiful landscapes and many other points of interest in this amazing region. Or relax and feel like you are at home. This charming well-maintained Villa in Stone is part of a complex of three buildings used for higher-level holiday homes.

Villa in Montopoli in Val D'arno

4.81 out of 5 average rating, 53 reviews

Villa Belvedere, beautiful view, surrounded by greenery

My place is close to art and culture, great views, family-friendly activities, restaurants and the beach. You'll love my place because of its atmosphere, outdoor spaces, and light. My accommodation is suitable for couples, sole adventurers, business travelers, families (with kids) and furry friends (pets).

Holiday rentals for every style

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Popular amenities for Siena villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Guest favourite

Villa in Bucine

4.96 out of 5 average rating, 23 reviews

Charming property, wi-fi, weddings ,cooking class

Guest favourite

Villa in Città della Pieve

4.88 out of 5 average rating, 16 reviews

Villa Miralaghi heated pool fitness park on a hill

Guest favourite

Villa in Torrita di Siena

4.88 out of 5 average rating, 69 reviews

Villa Poggio Becchi. Infinity pool and valley view

Guest favourite

Villa in Pergine Valdarno

4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

Guest favourite

Villa in Sarteano

5 out of 5 average rating, 12 reviews

Villa "La Civetta" with pool, sauna and jacuzzi

Villa in Provincia di Arezzo

4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

Guest favourite

Villa in Castelfranco di sotto

5 out of 5 average rating, 13 reviews

Villa Montefalcone: Charm, Private Pool, and Chef

Guest favourite

Villa in Vicopisano

4.86 out of 5 average rating, 7 reviews

Elegant luxury villa with private pool

Luxury villa rentals

Guest favourite

Villa in Sodo

4.95 out of 5 average rating, 22 reviews

The House of the Sodo Sun

Guest favourite

Villa in Montepulciano

5 out of 5 average rating, 17 reviews

Villa Nobile - Private Jacuzzi

Guest favourite

Villa in Casale

4.95 out of 5 average rating, 22 reviews

Villa with pool in chianti Rufina area 13 sleeps

Villa in Radda in Chianti

5 out of 5 average rating, 4 reviews

Villa Montemaggio

Guest favourite

Villa in San Miniato

4.88 out of 5 average rating, 40 reviews

Villa with exclusive pool

Villa in Fiesole

4.86 out of 5 average rating, 21 reviews

Villa Lualdi

Guest favourite

Villa in Pistoia

4.94 out of 5 average rating, 16 reviews

Villa De Fiori 14 by Tuscanhouses

Villa in Torrita di Siena,

5 out of 5 average rating, 4 reviews

Villa Scianellone

Villa rentals with a pool

Guest favourite

Villa in Baco

4.86 out of 5 average rating, 83 reviews

Tuscan Villa

Guest favourite

Villa in Montecucco

4.9 out of 5 average rating, 39 reviews

Villa Angiolina

Villa in Petrognano

4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

Villa in Capannori

4.94 out of 5 average rating, 16 reviews

Luxury Tuscany Villa on the hill with private pool

Villa in San Gimignano

4.78 out of 5 average rating, 23 reviews

Villa Elisa

Guest favourite

Villa in La Poggerina

4.97 out of 5 average rating, 37 reviews

Villa La Poggerina, private pool and amazing view

Guest favourite

Villa in Volterra

5 out of 5 average rating, 46 reviews

Villa Casa al Povero

Villa in Lastra a Signa

4.97 out of 5 average rating, 86 reviews

Casa Vacanze Il Noce - Villa with private pool

Quick stats about villa rentals in Siena

Total rentals
30 properties
Nightly prices starting at
$76 AUD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

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