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)
search | Pool: yes del
dates Select Dates for more accurate results
location
clear

calendar
group
search Filters   
2

  • Italy Siena:










    • Price per night:
    location City

       Tuscany Region
















































































































































































































































































    location Map
    fav

    Found 246 Siena holiday homes for rent

    Siena, House for rent
    House • 14 People • 7 • 7 • pool wifi
    From
    €
    2,347 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,347 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Hilltop Aria

    Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private parking is av...More Details


      • Booked Available
    Siena, House for rent
    House • 16 People • 8 • 9 • pool wifi
    From
    €
    2,626 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,626 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Sunlight Symphony

    This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. *Please note one of the bedrooms is located in the independent annexe. *If you're travelling with little ones, your host can provide a cot and two high chairs for free on request. *The swimming pool is available for use from May to September. Barbeque Child Friendly Coffee Maker Cot / Crib Dishwasher Dry...More Details


      • Booked Available
    Siena, House for rent
    House • 12 People • 6 • 6 • pets pool wifi
    From
    €
    2,939 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,939 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Golden Tuscan Sun

    Traditional charm, stunning views and a private swimming pool – this home has everything you could need for a blissful Italian escape. There are two outdoor seating areas, a barbecue and a pizza oven for delicious evening meals. Inside, the rooms are filled with art along with a range of home comforts to ensure optimum relaxation. Exercise enthusiasts will also appreciate the home gym. Daily housekeeping is included in your stay and your host can help organise a range of extra services – including private chefs and wine tastings. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Sarteano, while Montepulciano, Montalcino and Chianciano Terme are all within easy driving distance. *Housekeeping is included for four hours per day. *Please note this home is set across two floors with stairs. It is also possible for the bedrooms to be arranged with two single beds or as a double on request. *If...More Details


      • Booked Available
    Siena, House for rent
    House • 10 People • 5 • 5 • pool wifi
    From
    €
    1,497 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,497 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Gaze

    Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all the key ingredients for a relaxing stay. And the cherry on the cake for us is the outdoor space. A private pool, hot tub, sun-drenched terraces and views for miles – what’s not to love? Location-wise, it’s a short 5km drive to Gaiole, where authentic Tuscan eateries and wine tasting await. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The main bedroom is only accessible from outdoors. *One of the bedrooms can be set up as...More Details


      • Booked Available
    Advertisement
    Siena, House for rent
    House • 19 People • 10 • 11 • pool wifi
    From
    €
    9,159 /night
    Min Stay 1 night


    Siena, Italy 

    € 9,159 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    A Truffled Retreat

    This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar. While the home is perfectly set up for a large group, you can still get privacy when you need it – all of the bedrooms are en-suite and the second floor of the villa has its own entrance, as well as an extra lounge and kitchenette. And when you’re ready to explore, why not book a wine tasting at one of the local vineyards, or take a scenic drive to the picturesque town of San Gimignano – famous for its medieval towers and gelaterias? *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The outdoor swimming pool isn't fenced so children will need to be supervised at all times. The outdoor pool is only available for use between May and October. Th...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 10 People • 5 • 5 •
    From
    €
    3,218 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,218 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sunflower Hill

    This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. *This home is composed of three suites and two cottages, so you won’t all be sleeping under the same roof. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *Well-behaved pets are welcome to join you. ...More Details


      • Booked Available
    Siena, House for rent
    House • 16 People • 8 • 7 •
    From
    €
    2,167 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,167 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Embers - Sunlight

    This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. *This home consists of the main villa and an annex, so you won’t all be sleeping under the same roof. *Five bedrooms can be set up as doubles or twins – just let your host know which you’d prefer when you book. *The villa is spread over four floors, so it may not be suitable for those with reduced mobility. The swimming pool can ...More Details


      • Booked Available
    Siena, House for rent
    House • 12 People • 6 • 6 •
    From
    €
    2,566 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,566 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tuscan Time

    This contemporary villa is a stunning base for an Italian escape. It’s just a sixteen-minute drive from San Gimignano, with a winery only ten minutes away. The villa looks out over the surrounding hills and boasts views of San Gimignano and its historic towers. The outside space is beautiful, with a heated infinity pool at its heart. There’s also a great spot for alfresco dining on the terrace. Inside, the villa is timeless. It’s comfortable and stylish, a beautiful home-from-home with all the amenities you could wish for – there’s even a sauna. *One well-behaved dog is welcome to join you during your stay. *Your host can provide a cot and high chair for little ones. *There’s free parking and an electric vehicle charging point here. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *The minimum booking age for this home is 18. *Parties are not p...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 1 Person • 4 • 3 •
    From
    €
    1,098 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,098 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Siena Charm

    The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer. *You'll have access to the swimming pool here. It's shared with other guests staying nearby. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Free parking is available. *If you're travelling by plane, Florence is the n...More Details


      • Booked Available
    Siena, House for rent
    House • 14 People • 7 • 5 •
    From
    €
    2,389 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,389 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Super Tuscan

    Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *This home comes with its own private chef and team of staff who can help with anything you might need while always respecting your privacy. *The swimming pool isn't fenced. If you're bring...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 11 People • 7 • 4 •
    From
    €
    557 /night
    Min Stay 1 night


    Siena, Italy 

    € 557 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    The Forest - The Sea

    Retreat into nature at this Tuscan villa, perched on a hillside overlooking the Etruscan Coast. Lounge in the shade of ancient oak trees, admire the view from the picturesque swimming pool, or hop in the car to explore the countryside and coastline. Inside, you’ll find a home that’s full of character, with a charming living and dining area and a country-style kitchen for cooking up a feast. There are also seven comfortable bedrooms and four bathrooms, offering plenty of room to spread out and making this an ideal place for a family holiday or sharing with friends. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *The house is accessed via a well-maintained 3km dirt road. *There’s free parking on the driveway. *The wi-fi here doesn't reach all rooms, so you may find yourself without signal in some areas of the home. *At full occupancy, one guest will be sleeping on a pull-out bed. *The swimming ...More Details


      • Booked Available
    Siena, House for rent
    House • 8 People • 4 • 4 •
    From
    €
    1,389 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,389 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Vittoria

    This home is a handsome retreat in the heart of Val di Chiana. Outside, you can enjoy stunning views across olive trees and vineyards while lounging by the private pool. There are plenty of shaded areas for lazy afternoon reading sessions, while the terrace lends itself perfectly to evening drinks. The rooms are set across three independent cottages – all of which feature a kitchen and living room. It’s worth noting you will need a car to get around here, but it’s just a short drive to the village of Sinalunga where you’ll find restaurants and shops. It’s also the ideal base for exploring nearby Siena, Arezzo and Montepulciano. *Please note the rooms are set across three independent cottages – two cottages have one double bedroom, and one has two bedrooms. Each house includes a living area, a fully equipped kitchen and a private bathroom. *You may meet the owners and their staff during your stay. *Complimentary toiletries are provide...More Details


      • Booked Available
    Siena, House for rent
    House • 16 People • 6 • 6 •
    From
    €
    1,643 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,643 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Cypress Skies

    This stunning Tuscan villa is set amid rolling hills and cypress trees, offering breathtaking views of Pienza and the Val d’Orcia. The large garden blends seamlessly with the surrounding wheat fields, while the inviting pool and sun-drenched solarium promise total relaxation. Inside, rustic charm meets authentic tradition with terracotta floors, exposed beams, and restored antique furniture. A spacious hall on the ground floor is ideal for weddings or special events, with space for up to one hundred people. In addition to the upstairs bedrooms, there’s a fully equipped one-bedroom apartment in a separate annex. We'd recommend hiring a car, plus it's also worth noting the host doesn't accept group stays with guests under the age of twenty-three. It's otherwise the perfect place for a peaceful, unforgettable escape in the heart of Tuscany. *This home doesn’t accept group bookings for guests under the age of twenty-three. *Due to this ho...More Details


      • Booked Available
    Siena, House for rent
    House • 12 People • 6 • 6 •
    From
    €
    3,008 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,008 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Tuscan Embrace

    Nestled in the rolling Tuscan hills not far from Siena, this six-bedroom villa is packed with rustic character. The timber beams, exposed stonework, and other original features make staying here feel a little like stepping back in time – and we think that adds to the charm of the place. There’s lots of space to get comfortable, whether you’re on a family holiday or group getaway, but our favourite feature has to be the scenic swimming pool. With picturesque views over the surrounding countryside, it’s an extra-special spot to relax in the sunshine, whether you’re swimming leisurely laps or lounging poolside. Bellissimo. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *Due to this home's location, we recommend hiring a car to get the most out of...More Details


      • Booked Available
    Siena, House for rent
    House • 8 People • 4 • 4 •
    From
    €
    2,221 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,221 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sunset on the Landscape

    Take a look at the amazing views of the Tuscan hills and Siena from this traditional home – they really do stop you in your tracks. The gardens are a dream as well – perfect for alfresco dining and drinks as the sun sets on the stunning landscape beyond. There’s a shared pool to enjoy here too. Or relax in the living room with its open fireplace and characterful beams – it’s a cosy place to be. The large, farmhouse-style kitchen has everything you need to prepare unforgettable Italian meals. And, when you want to explore, the beautiful city of Siena, rich in history, is 10 kilometres away. *This house is set over two floors. *The swimming pool is shared with other guests at neighbouring homes. *The garden is terraced. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *Due to this home's location, we recommend hiring a car to get the most out of your sta...More Details


      • Booked Available
    Siena, House for rent
    House • 10 People • 5 • 5 •
    From
    €
    2,481 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,481 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Jade Hamlet

    Located in the heart of Tuscany, this expansive villa spans fifty hectares and is ideally suited for families or groups of friends. A tasteful blend of traditional features and luxurious interiors include impressive stone fireplaces, rustic wooden beams, and French doors. Enjoy alfresco dining for up to twenty guests, or spend your day lounging by the heated infinity pool, accompanied by the sound of the nearby river. With such a serene setting, it’s easy to forget that the Chianti region — with its wealth of places to see and things to do — lies just beyond the door. *While the bedrooms and bathrooms aren't photographed, expect the style and quality to be consistent with the rest of the home. *The fifth and final king-size bedroom is built into the original tower of the homestead. It's accessed via a preserved wooden staircase and offers 360-degree views of the property. *Three-hour morning cleaning is included daily with each stay....More Details


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


    Siena, Italy 

    € 239 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Ornate Haven

    In the hills of Crete Senesi and just a short drive from Siena, this rustic Tuscan farmhouse offers a peaceful retreat with views that stretch all the way to the Torre del Mangia. Traditional stone walls, tiled floors and countryside charm, make this the ultimate Italian home-from-home. Step outside and you'll discover a shaded loggia ideal for alfresco dining, and a private fenced pool, perfect for long summer afternoons in the sun. From setting off on day trips to nearby Chianti vineyards to simply relaxing under the Tuscan sky, this place invites you to slow down and savour the moment. *The home is set in the idyllic Crete Senesi hills, just 5km from Siena, so we would recommend a car for getting around. There is a free parking space in front of the house. *The interior living spaces are located on the first floor, so it may not be ideal for those with limited mobility. *The swimming pool is fenced – great for peace of mind if you'...More Details


      • Booked Available
    Siena, House for rent
    House • 8 People • 4 • 5 •
    From
    €
    544 /night
    Min Stay 1 night


    Siena, Italy 

    € 544 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Chianti Hills

    This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves. Inside the villa's stone walls you'll also find an abundance of regional charm, including terracotta floors, exposed beam ceilings, a pizza oven, and elegant living areas. However, arguably the jewel in its crown lies outside, in the form of a dazzling hillside infinity pool. And with the town of Gaiole in Chianti close by and the city of Florence around an hour away, local delights go far beyond wine. *You'll have access to the first and second floor of this home – your host lives on the ground floor, and can assist you during your stay while respecting your privacy. *The twin beds in the second bedroom can be converte...More Details


      • Booked Available
    Siena, House for rent
    House • 12 People • 6 • 4 •
    From
    €
    1,697 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,697 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    A Pure Light

    Dating back to the 19th-century, this farmhouse offers an abundance of character and timeless Italian charm. You’ll be treated to stunning views across cypress trees and olive groves. There’s also a private pool, a shaded pergola and an authentic stone barbecue for magical meals under the stars. Inside, you’ll find plenty of space to socialise and stretch out across the common areas and bedrooms. There’s also a games room with table tennis for family fun. You will need a car to get around here, but it’s just a short drive to the historic centre of Buonconvento, while Montalcino and Siena are also within easy driving distance. *The swimming pool is available for use from the last Saturday of April to the first Saturday in October. *This home is set across two levels connected by two internal staircases. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *It is possible for two of t...More Details


      • Booked Available
    Siena, House for rent
    House • 12 People • 6 • 6 •
    From
    €
    1,059 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,059 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Forever Light

    This Tuscan home is set within a peaceful garden just outside the small town of Sarteano. Offering tranquility and privacy, it’s the perfect setting for a slow Italian escape. There’s a private pool for refreshing swims, a terrace with a barbecue and outdoor games for family fun. Inside, the rooms are set across two independent apartments – making this a great option for groups looking to stretch out and spend quality time together. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while some of the most beautiful spots of Tuscany and Umbria are within easy reach. *Please note this home consists of two independent apartments. They are not connected internally. *It is possible for the bedrooms with single beds to be arranged as doubles on request. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *Please note the fireplace is ornamental. ...More Details


      • Booked Available
    Advertisement
    Page 5 of 13
    « Prev Page
    Next Page »
      Siena Holiday rentals
    3 4 5 6 7 8 9 ..13

    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