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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for villa rentals in Siena
Private villa rentals
Villa in Cortona
5.0 out of 5 average rating, 52 reviewsStunning Tuscan Villa & Panoramic Infinity Pool
22–29 Jan
Villa in Sovicille
4.97 out of 5 average rating, 30 reviewsI Susini
1–8 Dec
Villa in Sovicille
4.98 out of 5 average rating, 42 reviewsBeautiful Country House, near Siena with jacuzzi
4–11 Dec
Villa in Impruneta
4.96 out of 5 average rating, 25 reviewsLa Quercia Estate Quintessential ItalianExperience
14–21 Nov
Villa in Ulignano
5.0 out of 5 average rating, 8 reviews[Luxury Villa] Swimming pool and view of San Gimignano
10–17 Oct
Villa in Florence
5.0 out of 5 average rating, 15 reviewsCharming villa 10' walk to center stunning view
9–16 Sep
Villa in Siena
4.95 out of 5 average rating, 63 reviewsVilla il Borghetto_la DEPANDANCE
29 Aug – 5 Sep
Villa in San Leolino
5.0 out of 5 average rating, 92 reviewsPoggio del Fattore-Villa with pool,hilltop,Chianti
Luxury villa rentals
Villa in San Ginese di Compito
4.99 out of 5 average rating, 112 reviewsFarmhouse , pool, 13 px. Lucca 10km
14–21 Feb
Villa in Siena
4.93 out of 5 average rating, 15 reviewsVilla Le Tortore private luxury pool relaxation Siena
5–12 Feb
Villa in San Casciano
4.97 out of 5 average rating, 91 reviewsLuxury Villa in the very heart of Chianti
7–14 Feb
Villa in San Casciano In Val di Pesa
4.93 out of 5 average rating, 90 reviewsVillaCortevecchia PrivatePoolVineyard 15minFlorenc
14–21 Jan
Villa in Barberino Tavarnelle
5.0 out of 5 average rating, 20 reviewsValluccia 51
24 Nov – 1 Dec
Villa in Monticchiello
4.95 out of 5 average rating, 44 reviewsVilla with garden. Il Giardino del Cardinale.
2–9 Dec
Villa in Castiglion d'orcia
4.95 out of 5 average rating, 77 reviewsVilla Vignalunga
13–20 Nov
Villa in San Gimignano
5.0 out of 5 average rating, 11 reviewsExclusive villa private pool Florence and Sienna
17–24 Nov
Villa rentals with a pool
Villa in Montepulciano
4.95 out of 5 average rating, 116 reviewsA paradise in Montepulciano...
2–9 Feb
Villa in Casalguidi
4.79 out of 5 average rating, 68 reviewsCosy farmhouse appartment on 18th century estate
18–25 Dec
Villa in Montespertoli
4.93 out of 5 average rating, 145 reviewsColonica in the Chianti
12–19 Jan
Villa in Gambassi Terme
4.96 out of 5 average rating, 109 reviewsVilla Il Vecchio Pozzo in Tuscany
21–28 Dec
Villa in Monteroni D'arbia
4.97 out of 5 average rating, 74 reviewsSan Giovanni in Poggio, villa Meriggio 95sqm
11–18 Nov
Villa in Siena
4.92 out of 5 average rating, 52 reviewsIl Boschetto an oasis of peace and nature in Siena
27 Dec – 3 Jan
Villa in Volterra
5.0 out of 5 average rating, 18 reviewsPodere La Casetta - 2 People - Private Pool
2–9 Sep
Villa in Panzano In Chianti
4.92 out of 5 average rating, 64 reviewsLuxury Villa on Chianti Wine Estate
27 Feb – 6 Mar
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
€ 47 before taxes and fees
Destinations to explore
- Villa rentals Italy
- Villa rentals Florence
- Villa rentals Tuscany
- Villa rentals Tuscany
- Villa rentals Bologna
- House rentals Siena
- Serviced apartment rentals Siena
- Rentals with a hot tub Siena
- Fitness-friendly rentals Siena
- Flat rentals Siena
- Rentals with a patio Siena
- Rentals with breakfast Siena
- Bed and breakfasts Siena
- Rentals with a washing machine and dryer Siena
- Family-friendly rentals Siena
- Pet-friendly rentals Siena
- Apartment rentals Siena
- Rentals with outdoor seating Siena
- Boutique hotel rentals Siena
- Rentals with an EV charger Siena
- Holiday home rentals Siena
- Rentals with a fireplace Siena
- Rentals with a firepit Siena
- Smoking-friendly rentals Siena
- Monthly Rentals Siena
- Rentals with pools Siena
- Family-friendly rentals Siena
- Villa rentals Province of Siena
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom