Villa vacation rentals in Siena
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Top-rated villa rentals in Siena
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Siena villa rentals
Private villa rentals
Villa in Monteroni D'arbia
4.97 out of 5 average rating, 74 reviewsSan Giovanni in Poggio, villa Meriggio 95sqm
Nov. 11 – 18
Villa in Sovicille
4.97 out of 5 average rating, 30 reviewsI Susini
Dec. 1 – 8
Villa in Asciano
4.96 out of 5 average rating, 57 reviewsCasa Bianca gorgeous Tuscan home, Crete Senesi
Apr. 1 – 8
Villa in Sovicille
4.98 out of 5 average rating, 42 reviewsBeautiful Country House, near Siena with jacuzzi
Dec. 4 – 11
Villa in Ulignano
5.0 out of 5 average rating, 8 reviews[Luxury Villa] Swimming pool and view of San Gimignano
Oct. 20 – 27
Villa in Cortona
5.0 out of 5 average rating, 52 reviewsStunning Tuscan Villa & Panoramic Infinity Pool
Mar. 30 – Apr. 6
Villa in Siena
4.95 out of 5 average rating, 63 reviewsVilla il Borghetto_la DEPANDANCE
Aug. 29 – Sep. 5
Villa in Siena
4.94 out of 5 average rating, 16 reviewsVilla Le Tortore private luxury pool relaxation Siena
Dec. 28 – Jan. 4
Luxury villa rentals
Villa in Monsummano Terme
4.98 out of 5 average rating, 106 reviewsLe Maggioline : your panoramic country house
Dec. 24 – 31
Villa in San Ginese di Compito
4.99 out of 5 average rating, 113 reviewsFarmhouse , pool, 13 px. Lucca 10km
Nov. 24 – Dec. 1
Villa in Castiglion d'orcia
4.95 out of 5 average rating, 78 reviewsVilla Vignalunga
Nov. 2 – 9
Villa in San Casciano
4.97 out of 5 average rating, 91 reviewsLuxury Villa in the very heart of Chianti
Mar. 31 – Apr. 7
Villa in Poggibonsi
4.89 out of 5 average rating, 27 reviewsVilla with pool in Chianti Area
Apr. 15 – 22
Villa in Monticchiello
4.96 out of 5 average rating, 45 reviewsVilla with garden. Il Giardino del Cardinale.
Oct. 20 – 27
Villa in Montepulciano
4.96 out of 5 average rating, 75 reviewsWine Experience Villa in Montepulciano
Feb. 14 – 21
Villa in San Casciano In Val di Pesa
4.93 out of 5 average rating, 90 reviewsVillaCortevecchia PrivatePoolVineyard 15minFlorenc
Jul. 25 – Aug. 1
Villa rentals with a pool
Villa in Casalguidi
4.79 out of 5 average rating, 68 reviewsCosy farmhouse appartment on 18th century estate
Oct. 30 – Nov. 6
Villa in San Leolino
5.0 out of 5 average rating, 92 reviewsPoggio del Fattore-Villa with pool,hilltop,Chianti
Apr. 27 – May 4
Villa in Siena
4.92 out of 5 average rating, 53 reviewsIl Boschetto an oasis of peace and nature in Siena
Mar. 14 – 21
Villa in Panzano In Chianti
4.92 out of 5 average rating, 65 reviewsLuxury Villa on Chianti Wine Estate
Nov. 23 – 30
Villa in Barberino Tavarnelle
5.0 out of 5 average rating, 20 reviewsValluccia 51
Jan. 3 – 10
Villa in Volterra
5.0 out of 5 average rating, 18 reviewsPodere La Casetta - 2 People - Private Pool
Jun. 25 – Jul. 2
Villa in Cortona
4.93 out of 5 average rating, 40 reviewsVilla Le Vigne, 10 pax, private pool, Top Comfort
Oct. 15 – 22
Villa in Buonconvento
4.96 out of 5 average rating, 45 reviewsBellagatta, an Enchanting spot in Val d'Orcia
Feb. 22 – Mar. 1
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
$68 CAD before taxes and fees
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