
Holiday Homes in Siena
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Top-rated Holiday Homes in Siena
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"Lisa" apartment with fireplace
Lisa apartment is very romantic, the most peculiar of our farm.... You enter directly into a large living room with fireplace, dining table, two sofas and television. In this room there is a charming loft where the bed is located. Bathroom with bath, dressing room with closet and washing machine. Large kitchen with dining table and a view over the Chianti hills. This apartment has a private solarium with deck chairs and table.“Il Poderaccio” dates back to 13th century when its ancient building served as an outpost of Siena against the “League”. Dominating “Chiantishire” , this charming country house offers all recently refurbished, independent flats just a few minutes from Siena city centre. Perfectly integrated in the surrounding environment, the flats can host from 2 to 5 people and come complete with bed and bath linen, dishes and pottery and traditionally furnished with country furniture. Guests can swim in the 18x6-mt swimming-pool, sunbathe in the cotto sundeck surrounded by an orchard and flowers, play bowls and table tennis while children enjoy the playground in the garden or play in the beautiful park spotted with trees and flowers coming from all over the world. Garden areas are reserved for each flat together with sun chairs, garden table and chairs for a perfectly relaxing stay. Furthermore, two wooden desks are available in the shadow and perfect silence of a fenced-in grove where you can hear the birds singing … “Il Poderaccio” stretches for 32 hectares, all cultivated. This ICEA -controlled farm offers totally organic products such as wine, extra vergin olive oil and Grappa. On sale at the farm are: Chianti Colli Senesi DOCG, the “Brunaccio” a special IGT Tuscan red wine, extra virgin olive oil, and a grappa These organic products are the result of an environment- and consumer-friendly growing. “Il Poderaccio” hosts a lot of animals: horses, dogs, cats, a cow, a donkey, a kid as well as the geese, ducks and mallards swimming together in the farm pond. Horse trekking and riding can be organized upon request at a riding school renowned for its highly-qualified trainers situated near the farm. Mountain bikes rental is also available. All the flats are equipped with independent central heating thus being available all year round. NB: FOR WEEKLY STAYS THE AMOUNT OF THE HEATING WILL BE CALCULATED ON CONSUME
ValueFamilyCheck-in
4.83 out of 5 average rating, 103 reviews
Casa al Gianni - Oak
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!
FamilyLocationEV charging
4.93 out of 5 average rating, 246 reviews
Podere La Castellina - No. 4 FICO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of the Montagnola Senese. The apartment located on the first floor can comfortably accommodate 4 people (2+2 children) and includes: - large living room with TV, sofa and 2 single beds - eat-in kitchen with oven - master bedroom - bathroom with shower Panoramic pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue are available to guests.
ValueLocationAir conditioning
4.96 out of 5 average rating, 110 reviews
Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.
ValueLocationAccuracy
4.94 out of 5 average rating, 205 reviews
Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area
ValueLocationBiking
5.0 out of 5 average rating, 123 reviews
Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.
FamilyLocationBathroom
4.98 out of 5 average rating, 165 reviews
Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.
LocationFamilyCleanliness
4.88 out of 5 average rating, 229 reviews
In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
LocationValueCleanliness
4.96 out of 5 average rating, 137 reviews
La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
FamilyLocationDecor
4.99 out of 5 average rating, 104 reviews
AM Apartment
The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi
FamilyLocationHeating
4.89 out of 5 average rating, 206 reviews
[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
ValueLocationLayout
4.89 out of 5 average rating, 324 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
LocationFamilyCleanliness
4.91 out of 5 average rating, 100 reviewsPopular amenities for Siena holiday homes
Family-Friendly holiday homes

Linearis apt B (4+2) Toscana
LocationValueComfort
4.89 out of 5 average rating, 160 reviews
Charming farmhouse with garden, views & pool
FamilyLocationBathroom
4.92 out of 5 average rating, 233 reviews
The Eagle and the Olive Tree
FamilyLocationHospitality
5.0 out of 5 average rating, 129 reviews
Experience rustic off-grid life in the wilderness
FamilyLocationWalkability
4.97 out of 5 average rating, 159 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
ValueLocationKitchen
4.98 out of 5 average rating, 168 reviews
Chianti Penthouse with panoramic View & Pool
ValueLocationComfort
4.98 out of 5 average rating, 174 reviews
La Casa dei Ricordi - car/motorcycle garage at 650m
ValueFamilyAir conditioning
4.96 out of 5 average rating, 142 reviews
Tuja
FamilyLocationCheckout
5.0 out of 5 average rating, 35 reviewsHoliday home rentals with a patio

Il Toscano - New with terrace in downtown Greve
LocationValueGetting around
4.93 out of 5 average rating, 107 reviews
Pienzalettings
ValueFamilyCleanliness
4.92 out of 5 average rating, 115 reviews
I Rosai apartment on the Florentine hills
ValueLocationGetting around
4.9 out of 5 average rating, 270 reviews
Tuscan House with Private Jacuzzi in Chianti
ValueFamilyOutdoor spaces
4.95 out of 5 average rating, 97 reviews
Elegant farmhouse overlooking Pienza
LocationFamilyAmenities
5.0 out of 5 average rating, 36 reviews
The Piccola Villa of Borgo Argenina
FamilyLocationView
4.97 out of 5 average rating, 38 reviews
Tuscany Country House, Central Chianti, Pano Views
FamilyValueAccuracy
4.98 out of 5 average rating, 46 reviews
Tuscany Breath - Panoramic Pool & Tennis Court
LocationGetting aroundAccuracy
5.0 out of 5 average rating, 10 reviewsHoliday home rentals with a washing machine and dryer

[Florence Hills] Tuscan house with parking space
FamilyLocationOutdoor spaces
4.92 out of 5 average rating, 148 reviews
Duomo Charme – A few steps from the Duomo
ValueLocationWalkability
4.75 out of 5 average rating, 146 reviews
SMN Luxury Secret Garden View
LocationFamilyCheck-in
4.95 out of 5 average rating, 116 reviews
Zen Island downtown Florence, new apartment for 6
LocationFamilyCheck-in
4.94 out of 5 average rating, 103 reviews
Historic Center | Duomo • Ponte Vecchio
LocationFamilyWalkability
4.94 out of 5 average rating, 209 reviews
Melarancio Residence
ValueFamilyGetting around
4.91 out of 5 average rating, 361 reviews
TOSCANELLA APARTMENT
ValueLocationCheck-in
4.92 out of 5 average rating, 241 reviews
Chianti Panorama | House with 3 En-Suite Bathrooms
FamilyValueOutdoor spaces
4.95 out of 5 average rating, 147 reviewsWhen is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $203 NZD | $212 NZD | $270 NZD | $298 NZD | $294 NZD | $292 NZD | $285 NZD | $256 NZD | $292 NZD | $305 NZD | $261 NZD | $249 NZD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Rentals with breakfast Siena
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Things to do Siena
- Food tours Siena
- Cultural tours Siena
- Cooking Siena
- Tastings Siena
- Things to do Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Cultural tours Siena
- Art workshops Siena
- Outdoors Siena
- Dining Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
- Food tours Tuscany
- Shopping and fashion Tuscany
- Dining Tuscany
- Performances Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy







