English Languages

Change Language

EN FR DE ES IT NL PT RU
Italy  Italy - Holiday Rentals in Siena Italy
Italy Country: Italy (11002) | Region: Tuscany (3452)
dates Select Dates for more accurate results
location
clear

calendar
group
search Filters   
1

  • Italy Siena:










    • Price per night:
    location City

       Tuscany Region
















































































































































































































































































    location Map
    fav

    Found 268 Siena holiday homes for rent

    Siena, Apartment for rent
    Apartment • 4 People • 2 • 2 • pets pool wifi
    From
    €
    238 /night
    Min Stay 1 night


    Siena, Italy 

    € 238 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Chianti Haze

    Nestled in the heart of Chianti, this charming ground-floor apartment promises a tranquil retreat surrounded by nature. Set on a resort, there are shared facilities such as a communal swimming pool, table football, table tennis, boules court and children’s playground here – so, plenty to keep you entertained on days at home. You may also choose to take to the hiking trails through the pine and oak forest of Monte Luco. When you’re ready to explore, Gaiole is a mere 8-kilometre drive away, where shops and authentic Italian eateries await. *This home is set on a resort. Expect to see other guests during your stay. *There are communal facilities to enjoy here, including a swimming pool, open between May and October, a children's playground, table football, table tennis, and boules court. They're shared with the resort's other residents. *If you're travelling with little ones, your host can provide a free cot and high chair upon request....More Details


      • Booked Available
    Siena, Cottage for rent
    Cottage • 4 People • 2 • 2 • pool wifi
    From
    €
    307 /night
    Min Stay 1 night


    Siena, Italy 

    € 307 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Flow

    Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure. *This home is set on a resort. Expect to bump into other guests during your stay. *You'll have access to the communal swimming pool and tennis court here. They're shared with the resort's other residents. *The swimming pool is only available for use between Easter and October. *Playing equipment is not provided for the tennis court. If you'd like to play tennis, you'll need to bring your own racquets and balls. *The bedr...More Details


      • Booked Available
    Siena, House for rent
    House • 6 People • 3 • 5 • pool wifi
    From
    €
    603 /night
    Min Stay 1 night


    Siena, Italy 

    € 603 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sangiovesece Scenery

    In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures. *One of the double beds can be converted into two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *A separate pool house has a kitchen, living area, bathroom, and gym. *The swimming pool is available to use between May and September. *We suggest hiring a car in this area. Parking is available on the grounds. Air Con...More Details


      • Booked Available
    Siena, House for rent
    House • 2 People • 1 • 1 • pets wifi
    From
    €
    276 /night
    Min Stay 1 night


    Siena, Italy 

    € 276 /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    Crisp Chianti

    Once a hay barn, now a romantic retreat for two, this villa has tranquillity running through its core. Set on an estate surrounded by vineyards that produce some of the region’s most prestigious wines, it’s not hard to relax here. We love the open-plan concept indoors, while outdoors, the hot tub is just the spot to soak up the sun as you watch the world go by. The heart of the estate is two-and-a-half kilometres away, where you can enjoy castle tours, wine tastings, a bar and a restaurant. Further afield, you’ll find Gaiole a short drive away when you’re ready to explore more of the surrounding area. *This home is set on an estate. Expect to see other guests and/or vineyard workers during your stay. *The hot tub is available for use between 1st May and 15th October. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Due to this home's location, we recommend hiring a car to get the...More Details


      • Booked Available
    Advertisement
    Siena, Apartment for rent
    Apartment • 2 People • 1 • 1 • pool wifi
    From
    €
    430 /night
    Min Stay 1 night


    Siena, Italy 

    € 430 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    A Memorable Vintage

    This chic couple’s retreat is perfect for immersing yourself in the Tuscan lifestyle. Set on a winery, with a tour and tasting session included in your stay, you can truly savour what this region is all about. Modern interiors rub shoulders with tradition here, so relaxation comes easily. And where better than the outdoor space? Views of the rolling hills, a private pool, sun-drenched terraces and alfresco dining – it ticks all the boxes. Locally, you can enjoy Italian feasts in the charming town of Gaiole, a short walk away. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May to September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *This home is set within the grounds of a winery. A tour of the winery and a tasting session is included in the booking. *The fireplace in this home is purely decorative. *Ther...More Details


      • Booked Available
    Siena, House for rent
    House • 27 People • 14 • 13 •
    From
    €
    3,808 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,808 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti - Vines

    Perched on a Chianti hillside, this expansive estate comprises the main villa and two beautifully restored barns – an ideal setting for large groups, retreats or unforgettable celebrations. From the terraces, you’ll enjoy views that stretch from Monte Amiata to Siena, with vineyards unfolding in every direction. Traditional Tuscan through and through, the interiors might not suit modernists, but for those drawn to character and heritage, it’s a dream. Outside, you’ll find a pool, alfresco dining areas and plenty of quiet corners for aperitivos. Your host can arrange everything from private chefs to wine tastings, too. Plus, with medieval hamlets, castles and thermal spas just a short drive away, there’s no shortage of ways to explore the region. *This home is spread across a main house and two converted barns. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the o...More Details


      • Booked Available
    Siena, House for rent
    House • 21 People • 11 • 11 •
    From
    €
    3,868 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,868 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Classico Chianti

    This hilltop villa offers panoramas from Monte Amiata to Siena and boasts sweeping vineyard views – what more would you wish from a stay in the Chianti region? Licensed for weddings, it's a magical setting for special occasions – just ask your host for details. The interiors lean traditional, perfect for those who appreciate classic Tuscan charm. That said, you’ll likely want to spend most of your time outdoors – taking dips in the pool, sipping wine on one of the terraces and gathering for alfresco meals – your host can arrange private chefs, too. And with castles, medieval villages, vineyards and thermal spa towns within easy driving distance, you’ll be spoilt for choice here. *This home is spread across a main house and a converted barn. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the option to convert the double beds into two singles upon request. There a...More Details


      • Booked Available
    Siena, Townhouse for rent
    Townhouse • 4 People • 2 • 2 •
    From
    €
    220 /night
    Min Stay 1 night


    Siena, Italy 

    € 220 /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    Chianti Classic

    If you fancy living like a Tuscan local, this chic townhouse in the heart of Radda will be right up your street. Set across three floors, it’s an ideal base for two couples, with the bedrooms on separate floors and the living area in between, allowing plenty of opportunity for privacy, or to come together to socialise. Location-wise, you’re in for a treat. Wander into town to pick up some freshly baked bread, or dine out daily at one of the many authentic Italian eateries nearby – there’s something for everyone here. *This home is set across three floors. It may not be the best option for those with reduced mobility. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *This house is set in a pedestrianised area. Public parking is available off-premises. Air Conditioning Balcony Child Friendly Coffee Mak...More Details


      • Booked Available
    Siena, House for rent
    House • 4 People • 2 • 2 •
    From
    €
    660 /night
    Min Stay 1 night


    Siena, Italy 

    € 660 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Chianti Grape

    If you’re looking for an escape from it all, this could be the home for you. Set on a private road deep in the woods, this Chianti villa has tranquillity running through its core. We love the seamless blend of modern furniture with the traditional building here, but the outdoor space is our biggest winner. Sun-kissed terraces, a hot tub, a private pool, alfresco dining areas – what’s not to love? If you can tear yourself away, it’s a mere ten-minute drive to the wine-making town of Gaiole, which is well worth a visit. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *Due to this home's location, we recommend hiring a car to get the most out...More Details


      • Booked Available
    Siena, House for rent
    House • 6 People • 4 • 3 •
    From
    €
    513 /night
    Min Stay 1 night


    Siena, Italy 

    € 513 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    A Tuscan Escape

    Tucked in the Tuscan countryside, yet just five kilometres from Siena, this traditional home is perfect for those seeking a tranquil retreat. Should you need anything during your stay, the owner lives on-site – but your peace won’t be disturbed otherwise. With space to spread out, there are plenty of quiet nooks here when you’d like some privacy. That said, we think everyone will be drawn to the outdoor space. A private pool, sun-drenched terraces, and an alfresco dining spot nestled in the shade – it ticks our holiday boxes. *The swimming pool, available from May to September, isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *The twin bedroom can be set up as a double upon reque...More Details


      • Booked Available
    Siena, House for rent
    House • 10 People • 5 • 5 •
    From
    €
    1,950 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,950 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Glow

    Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. *This home consists of the main villa (sleeping six), a separate cottage (sleeping two), and an annexe (sleeping two). *The villa is situated on a winery but is private. That said, expect to see staff working at the vineyard from time to time. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming p...More Details


      • Booked Available
    Siena, House for rent
    House • 6 People • 3 • 3 •
    From
    €
    825 /night
    Min Stay 1 night


    Siena, Italy 

    € 825 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Hilltop

    This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Fan Fenced Property Fireplace Freezer Fridge Garden Hair Dryer High Chair Kitchen Kitchen Utensils Microwave Mosquito Net Outdoor Seating Oven Parking Availa...More Details


      • Booked Available
    Siena, House for rent
    House • 17 People • 9 • 9 •
    From
    €
    3,053 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,053 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Winery Way

    This beautiful home is perfect for celebrations and special occasions. The hilltop villa boasts panoramic views from Monte Amiata to Siena in the lap of Val d’Orcia, a UNESCO World Heritage Site. The restored stone property is a winery licensed for events, and with its terracotta floors, vaulted ceilings, and antiques, it’s bound to impress. There are multiple living areas and a professional kitchen, as well as a garden with stunning vistas and a gorgeous alfresco dining space. Whether you’re staying here for an event or just want an elegant home-from-home in Italy, this villa is sure to make for a memorable stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms are suitable for those with reduced mobility. *Bedroom eight can be set up with twin beds or a double Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Dr...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 4 People • 2 • 2 •
    From
    €
    175 /night
    Min Stay 1 night


    Siena, Italy 

    € 175 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sunlight Embrace

    Set in the pretty town of Gaiole, this apartment makes it easy to experience the magic of Tuscany. From here, you can stroll to local restaurants, shops and cafes. It’s also possible to drive to Siena, San Gimignano, Florence and Arezzo for inspiring day trips. And when it comes to total relaxation, this home has everything you could need. There’s a private pool for refreshing drips and three terraces set across different levels. You can also enjoy freshly picked produce from the vegetable patch and there’s a barbecue for alfresco dining. *Please note the apartment is located in the owner’s house. *It’s worth noting some of the furnishings are a little dated here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to September. *Private parking is available here. Air Conditioning Barbeque Beach / Pool Towels Child Frie...More Details


      • Booked Available
    Siena, House for rent
    House • 4 People • 2 • 2 •
    From
    €
    258 /night
    Min Stay 1 night


    Siena, Italy 

    € 258 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Vines - Serenity

    Wrapped in vineyards and olive groves, this cosy villa in the heart of the Chianti countryside promises a serene escape from daily life. It’s not the biggest inside, but it’s more than comfortable for a family, and with the Tuscan sun shining, everyone will naturally be drawn to the outdoor space. We love the private pool and choice of sunny and shaded spots to relax, all whilst soaking up the far-reaching views. Location-wise, hop in the car and you can reach Lecchi in three minutes or Radda in ten. Peppered with restaurants, they’re both perfect options when you crave authentic Italian cuisine. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May to September, can be fenced upon request. Speak to your host for more details. *The twin bedroom can be set up as a double upon request. You'll need to let your host know at the time of booking. *One well-be...More Details


      • Booked Available
    Siena, House for rent
    House • 4 People • 2 • 2 •
    From
    €
    627 /night
    Min Stay 1 night


    Siena, Italy 

    € 627 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sweet Vin Santo

    Nestled in the heart of Tuscany's renowned Chianti Classico wine region, this villa offers a tranquil escape from it all. Owned by a local winery and surrounded by vineyards, a spot of wine tasting during your stay is a must. The home itself is perfect for a family or small group of friends, and while the interiors are charming, it’s the outdoor space that caught our eye. With far-reaching views, a private pool and terraced dining areas, making the most of the Mediterranean climate will be high on your agenda. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until October, isn't fenced and there are open tread stairs here. Children will need to be supervised at all times. *The bedrooms can be set up as doubles or twins upon request. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *The ceiling ...More Details


      • Booked Available
    Siena, House for rent
    House • 8 People • 4 • 3 •
    From
    €
    547 /night
    Min Stay 1 night


    Siena, Italy 

    € 547 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Roses of Chianti

    With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private swimming pool and a serene terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional and family friendly with plenty of space to stretch out across the three floors. Your host is on hand to help organise extras like private chefs and guided tours. Plus, it’s just a short drive to Gaiole in Chianti where you’ll find the nearest restaurants, bars and shops. *Please note the owners live in an apartment at the rear side of the villa with their dog. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Well behaved dogs are welcome to join you here, but please note they need to be kept on a lead when...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 6 People • 2 • 1 •
    From
    €
    193 /night
    Min Stay 1 night


    Siena, Italy 

    € 193 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Tuscan Song

    If you’re in search of a traditional Italian escape with plenty of character, this apartment delivers a wonderful solution. Nestled in an old farmhouse, you’ll find snug rooms, original features and all the basics you could need to make it your own. There’s also a private terrace with a barbecue and you’ll have access to a shared swimming pool. You will need a car to get around here, but it’s a great base for exploring the Chianti countryside with Galenda, Florence and Siena all within driving distance. *This apartment is located in a farmhouse with a shared swimming pool. The swimming pool is available for use from 1st June to 30th September. *At full occupancy, two guests will be sleeping on the sofa bed in the living room. *Please note the apartment is set across two levels with steps. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *If you're travelling with little ones, your hos...More Details


      • Booked Available
    Siena, House for rent
    House • 6 People • 3 • 3 •
    From
    €
    476 /night
    Min Stay 1 night


    Siena, Italy 

    € 476 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Splendour

    With far-reaching views of the rolling Chianti hills, it’s impossible not to relax in this villa. Traditional yet modern, this home promises a true taste of Tuscany, alongside plenty of space to relax. We love the three tiered terraces, each offering something different – alfresco dining on the top terrace, bowls on the middle, and a private pool on the lower. And, being situated next to a working winery, you’re perfectly placed for a spot of wine tasting and some authentic Tuscan food – all of which can be organised by your host. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The twin bedroom can be set up as a double upon request. *There are stairs to climb here, including in the outdoor space to access different terraces. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of your stay – on-site parking is available f...More Details


      • Booked Available
    Siena, House for rent
    House • 2 People • 1 • 1 •
    From
    €
    384 /night
    Min Stay 1 night


    Siena, Italy 

    € 384 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sweet Tuscany

    Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. *The owners live in a separate villa above with dogs that are fenced in. They won't disturb you during your stay, but are on hand should you have any questions. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair...More Details


      • Booked Available
    Advertisement
    Page 4 of 14
    « Prev Page
    Next Page »
      Siena Holiday rentals
    2 3 4 5 6 7 8 ..14

    Siena Property for rent

    Houses for rent in Siena (109) Apartments for rent in Siena (149) Rooms for rent in Siena (2) Townhouses for rent in Siena (2) Cottages for rent in Siena (6)
    Vacation Rentals in Siena :
    Pet friendly rentals in Siena Rentals with Wifi in Siena With pool rentals in Siena See more...

    Available Information about Siena Italy
    Currently no location information is available for Siena Italy
    Trending Holiday rentals in Siena Italy Searches:
    Reduced holiday lets in Siena Luxury holiday lets in Siena Waterfront holiday lets in Siena Seaview holiday lets in Siena
    Search Long Term Rentals:
    Longer term rentals in Siena
    Search properties for sale:
    Property for sale in Siena

    Sub-Regions/Areas in Tuscany ArezzoFirenzeFlorenceGrossetoLivornoLuccaMassa-CarraraPisaPistoiaPortoferraioPratoSassariSiena
    network
    Advertise your property for Free.
    Our unique distribution network reaches millions of visitors each and every month.
    Create your Free account here!
    up
    Viewed

    RentHolidayHome.com
    Language
    EN FR DE ES IT NL PT RU
    cards
    Copyright © Holprop LTD. All Rights Reserved. Use of this website constitutes acceptance of our Terms of Use & Cookie Policy