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Villa vacation 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.

Guest favorite
Villa in Castellina in Chianti
The Villino Farmhouse
Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area
Oct 23 – 30
$516 per night
4.93 out of 5 average rating, 164 reviews
Guest favorite
Villa in Siena
Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hysterical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs there is a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private parking and the garden. The property also provides free wifi, air conditioning.
Sep 1 – 8
$177 per night
4.97 out of 5 average rating, 148 reviews
Guest favorite
Villa in Siena
Fascinating Villa Senese with View!
Old restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time flows slowly according to ancient traditions. One of the most beautiful views that the Tuscan view can give, exclusive pool, large triple garden, BBQ, BBQ, poolside table, terrace to enjoy the sunset on the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, free parking, WI-FI internet, WI-FI.
Jan 31 – Feb 7
$705 per night
4.9 out of 5 average rating, 252 reviews

Popular amenities for Siena villa rentals

Private villa rentals

Guest favorite
Villa in Sovicille
Podere La Castellina - N°1 COTTAGE
Sep 23 – 30
$206 per night
4.97 out of 5 average rating, 121 reviews
Guest favorite
Villa in Tignano
The best stay in Tuscany Spring
Apr 14 – 21
$483 per night
4.95 out of 5 average rating, 145 reviews
Guest favorite
Villa in Cavriglia, Arezzo
Villa Poggio a Mandria in Chianti
May 2 – 9
$581 per night
4.99 out of 5 average rating, 110 reviews
Superhost
Villa in Greve in Chianti
Villa La Doccia, Greve in Chianti.
Apr 22 – 29
$266 per night
4.86 out of 5 average rating, 135 reviews
Guest favorite
Villa in Capannori
La Dimora Dei Conti: Indulge in Country Farmhous
Jul 9 – 16
$195 per night
4.91 out of 5 average rating, 169 reviews
Guest favorite
Villa in Asciano
Casa Bianca gorgeous Tuscan home, Crete Senesi
Dec 20 – 27
$387 per night
4.96 out of 5 average rating, 51 reviews
Guest favorite
Villa in Siena
Villa Le Tortore private luxury pool relaxation Siena
Oct 20 – 27
$374 per night
4.92 out of 5 average rating, 12 reviews
Guest favorite
Villa in San Gimignano
SAN GIMIGNANO ★★★★★ LUXURY DESIGN FARMHOUSE
Aug 28 – Sep 4
$654 per night
4.92 out of 5 average rating, 53 reviews
Guest favorite
Villa in Monteroni D'arbia
San Giovanni in Poggio, villa Meriggio 95sqm
Nov 10 – 17
$218 per night
4.99 out of 5 average rating, 68 reviews
Guest favorite
Villa in Monteroni D'arbia
"Villa Daisy" overlooking Siena
Feb 15 – 22
$146 per night
4.97 out of 5 average rating, 88 reviews
Guest favorite
Villa in Sovicille
Beautiful Country House, near Siena with jacuzzi
Oct 29 – Nov 5
$165 per night
4.98 out of 5 average rating, 40 reviews
Guest favorite
Villa in Siena
Panoramic Villa Larniano Private pool 14 max
Nov 14 – 21
$786 per night
5.0 out of 5 average rating, 10 reviews

Luxury villa rentals

Guest favorite
Villa in Montepulciano
A paradise in Montepulciano...
Jul 19 – 26
$705 per night
4.95 out of 5 average rating, 115 reviews
Guest favorite
Villa in Monteroni D'arbia
Private Villa near Siena - Exclusive Spa,Gym,Pool
Nov 19 – 26
$912 per night
4.92 out of 5 average rating, 24 reviews
Luxe
Villa in Siena
Il Fienile Di Montesoli
Apr 11 – 18
$774 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Villa in Montepulciano
Villa Nobile - Private Jacuzzi
Nov 6 – 13
$811 per night
5.0 out of 5 average rating, 9 reviews
Guest favorite
Villa in Barberino Tavarnelle
Valluccia 51
Dec 16 – 23
$542 per night
5.0 out of 5 average rating, 20 reviews
Guest favorite
Villa in Gaiole In Chianti
Sestuccia
Dec 7 – 14
$553 per night
5.0 out of 5 average rating, 31 reviews
Guest favorite
Villa in San Gimignano
Truly Tuscan villa with pool 6km to San Gimignano
Oct 29 – Nov 5
$650 per night
5.0 out of 5 average rating, 37 reviews
Guest favorite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Jan 28 – Feb 4
$553 per night
4.96 out of 5 average rating, 70 reviews
Guest favorite
Villa in Monticchiello
The Cardinal's Garden.
Nov 3 – 10
$732 per night
4.95 out of 5 average rating, 42 reviews
Guest favorite
Villa in Lucolena In Chianti
Chianti Tuscany: villa with view
Oct 19 – 26
$515 per night
4.95 out of 5 average rating, 42 reviews
Guest favorite
Villa in Castiglion d'orcia
Villa Vignalunga
Mar 6 – 13
$553 per night
4.95 out of 5 average rating, 74 reviews
Guest favorite
Villa in Asciano
Villa Padronale in Agriturismo Tenuta La campana
Nov 29 – Dec 6
$503 per night
5.0 out of 5 average rating, 18 reviews

Villa rentals with a pool

Guest favorite
Villa in Gambassi Terme
Villa Il Vecchio Pozzo in Tuscany
Dec 30 – Jan 6
$132 per night
4.96 out of 5 average rating, 108 reviews
Guest favorite
Villa in Gambassi Terme
Il Leccio - Tuscany home near San Gimignano
Apr 13 – 20
$215 per night
4.88 out of 5 average rating, 128 reviews
Guest favorite
Villa in Buonconvento
Bellagatta, an Enchanting spot in Val d'Orcia
May 11 – 18
$304 per night
4.96 out of 5 average rating, 45 reviews
Guest favorite
Villa in Montenero d'Orcia
Tuscany Villa With Pool & Magnificent Garden
Apr 6 – 13
$597 per night
5.0 out of 5 average rating, 12 reviews
Guest favorite
Villa in Siena
Villa "La Scuola" "The Charming School"
Oct 22 – 29
$636 per night
4.92 out of 5 average rating, 59 reviews
Guest favorite
Villa in San Leolino
Poggio del Fattore-Villa with pool,hilltop,Chianti
Sep 21 – 28
$379 per night
5.0 out of 5 average rating, 92 reviews
Superhost
Villa in Scrofiano
SacroFanum Villa
Oct 22 – 29
$252 per night
4.84 out of 5 average rating, 75 reviews
Guest favorite
Villa in Gambassi Terme
Villa Via Francigena
May 11 – 18
$390 per night
4.97 out of 5 average rating, 33 reviews
Superhost
Villa in Castellina in Chianti
I CIPRESSINI DEL CASTELLACCIO (Cip 1 + Cip 2)
Dec 26 – Jan 2
$453 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Villa in Colle di Val d'Elsa
Villa with pool in the heart of Tuscany
May 21 – 28
$257 per night
4.97 out of 5 average rating, 30 reviews
Guest favorite
Villa in Radicondoli
Casa di Leo Romantic House
Dec 1 – 8
$260 per night
5.0 out of 5 average rating, 35 reviews
Superhost
Villa in Toscana
Chianti Villa Mulino del Cerchiaio
May 17 – 24
$434 per night
4.86 out of 5 average rating, 50 reviews

Quick stats about villa rentals in Siena

Total rentals

30 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Villa rentals