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  1. Home
  2. Luxury Villas In Tuscany For Rent
  3. Siena (Sienna) Villas & Vacation Rentals – Luxury Villas In Tuscany
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 Villas in Siena (Sienna): Vacation Rentals

Siena (often spelled by Americans and British as Sienna) is one of the most magnificent gems of Italy and TuscanDream delights in presenting the most spectacular castles and villas in Siena (Sienna) as well as hotels for you to enjoy this magical hillside city – home to the famous Palio horse race and the breathtaking Piazza del Campo.

Siena is far more than just the city itself.  Siena is also the province, which features the historic UNESCO World Heritage city of San Gimignano – the town of 1,000 towers – and the stunningly beautiful towns of Montalcino, Montepulciano and Pienza, the home of the Brunello grapes where our famous Super Tuscan wines come from.

TuscanDream is proud to offer the best of the best of the fabulous vineyard castles and villas in Siena (Sienna) for your dream holiday in Tuscany!   Many of our villas in Siena (Sienna) are air-conditioned, and all can be booked with staff!

Experience Siena (Sienna) – from Architecture to Romance

We love the charm of the Sienese architecture, as villas in Siena are generally built with stone facades, beamed ceilings, red terracotta floors and feature lovely gardens.  Many of these villas have been featured in famous movies including Stealing Beauty by Bernardo Bertolucci released in 1996 and more recent films like Letters to Juliet in 2010.

Let us know your style and taste and we will help you to identify the villa that fits you and your group personalities and interests. All the villas in the Siena region are within a short drive to the city.

Siena villa rentals give you the chance to enjoy the countryside life during the day and be only a short drive from the city’s walls for a romantic dinner in Piazza del Campo.  We invite you to explore the side streets of the Piazza del Campo which will with their beauty and grace – as well as with their excellent shopping and gourmet restaurants!

We invite you to contact TuscanDream and we will pamper you every step of the way to make sure your Siena vacation is the holiday of your dreams!

Villa Volterra – Modern Luxury Villa

3 Bedrooms | 4 Bathrooms
Luxurious, Jacuzzi & Gym

Contemporary Style 5 bedroom villa near Montalcino – Poggino

5 Bedrooms | 5 Bathrooms
Fully air conditioned with spa & jacuzzi

5 bedroom luxury Siena House, Tuscany

5 Bedrooms | 5 Bathrooms
Luxury Siena House walking distance to town

Monticelli – Luxury Rental Home in Tuscany with pool and gym

South of Siena | 6 Bedrooms | 6 Bathrooms
6 bedroom villa with en-suite bathrooms - AC, Pool, Gym

Luxury Siena Villa with Spa and Tennis court – Serravalle

5 Bedrooms | 5 Bathrooms
Luxury Siena Villa with spa and tennis court

Villa Sambuco – 6 bedroom luxury villa in Valdorcia, Tuscany

Valdorcia | 6 Bedrooms | 6 Bathrooms
Air Conditioned, wifi, infinity pool

il Padiglione, Historic Estate

Siena | 2 Bedrooms | 2 Bathrooms
Air Conditioned, Wi-Fi, outdoor jacuzzi

4-Bedroom Montepulciano Luxury Villa with Heated Pool for Rent

Montepulciano | 4 Bedrooms | 4 Bathrooms
Air Conditioning, Wi-Fi, Heated Pool

Villa Corsanello – Villa close to Siena

Monteroni d'Arbia | 4 Bedrooms | 3 Bathrooms
Wi-Fi, Air Conditioned in the bedrooms

Molino Sant’ Antimo – Vacation Rental in Montalcino Siena

Montalcino | 4 Bedrooms | 3 Bathrooms
Air Conditioned, Wi-Fi

Villa Boscarello, 14 bedroom air conditioned siena villa

Trequanda | 14 Bedrooms | 12 Bathrooms
Air Conditioned, Wi-Fi

Discover the Siena Italy Horse: Rent a Staffed Villa with Horses

Monticiano | 14 Bedrooms | 17 Bathrooms
Air Conditioned, Full Staff, Wi-Fi, Horses

Villa Collalto – 16 bedroom estate

Colle Val D'Elsa | 16 Bedrooms | 21 Bathrooms
AC, Fully Staffed, Concierge, Wi-Fi

Villa Cetinale

Sovicille | 12 Bedrooms | 14 Bathrooms
Air Conditioned, Full Staff, English Speaking Concierge, Wi-Fi

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