Holiday Homes in Siena

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Siena and around

Il Palazzetto
Premium Apartment, 2 Bedrooms, 2 Bathrooms, Annex Building | Lanai

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto
Villa Le Tortore Tuscany private luxury pool relax
Pool

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (90)
"Very convenient to town and to surrounding wine regions - very good communication with host and was comfortable to stay for 3 people. Would stay again if in the area"
Villa Le Tortore Tuscany private luxury pool relax
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Outdoor dining

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Outdoor pool

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (60)
"We spent 3 weeks in Europe from Barcelona to Cadaques to Provence to Cannes to Nice to Monaco to Rome and Castellina in Chianti. Our stay in Stella at this location was our absolute favorite. Federico was very kind kind, greeted us upon arrival, helped us with questions, and gave us suggestions around the area. We highly recommend this place and are already making our plans to return."
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Holiday Home for 8 guests
Pool

Holiday Home for 8 guests

8.0 out of 10, Very good, (2)
"Fantastisch huis, alles wat je nodig hebt, mooi uitzicht, dichtbij de stad"
Holiday Home for 8 guests
Beautiful stone house with garden and private pool.
Property grounds

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (63)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.
detached villa with private pool and garden
Pool

detached villa with private pool and garden

8.8 out of 10, Excellent, (24)
"Good location to the town and lovely garden space"
detached villa with private pool and garden
old barn on Via Francigena
3 bedrooms, desk, iron/ironing board, travel cot

old barn on Via Francigena

9.8 out of 10, Exceptional, (12)
" Very nice place and Sara just awesome"
old barn on Via Francigena
L'Oliviera by Interhome
Exterior

L'Oliviera by Interhome

9.8 out of 10, Exceptional, (6)
"Das Haus war etwas schwer zu finden (ist nicht über Navi zu finden), jedoch gaben uns die Vermieter eine genaue Anfahrtsbeschreibung per Mail. Zum Empfang standen eine Flasche Wein, sowie eine Schale mit Süßigkeiten auf dem Tisch. Kurze Zeit später brachte der Vermieter noch eine Schale mit frischen Erdbeeren vorbei. Das Ehepaar ist sehr freundlich, und Laura spricht fließend Englisch, sodass eine Unterhaltung stets möglich war. Im Garten gibt es einen Grill, Sonnenliegen und einen überdachte...
L'Oliviera by Interhome
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Outdoor dining

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (14)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Outdoor pool

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (33)
"Perfekt ferie🤗"
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Chianti Classico Home Panoramic View, Castellina in Chianti, Italy
Interior

Chianti Classico Home Panoramic View, Castellina in Chianti, Italy

10.0 out of 10, Exceptional, (1)
"Lovely, large home above the Farmacia in Castellina in Chianti. Charming village, wonderful food & atmosphere. Easy drive to many sites. Very good response from Roberto when I had some questions @ the house. We stayed a month & loved it. Highly recommend. "
Chianti Classico Home Panoramic View, Castellina in Chianti, Italy
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Interior

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (18)
"The apartment is very large, beautifully decorated, and is in a fantastic location in Siena. Couldn't be better..... Gianluca was the perfect host. We were very happy!!! Will rent again for sure!!!"
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Property grounds

Cozy Tuscan-style apartment Suitable for families. Pets allowed

The price is €169
includes taxes & fees
1 Sept - 2 Sept
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Family Tuscany Home Close Via Francigena, Monteriggioni, Italy
Outdoor dining

Family Tuscany Home Close Via Francigena, Monteriggioni, Italy

Family Tuscany Home Close Via Francigena, Monteriggioni, Italy
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Outdoor dining

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

10.0 out of 10, Exceptional, (13)
"The setting is truly incredible! Stunning views, a well kept and comfortable house to stay in. We spent lots of family time in the pool and loved being just 15 minutes outside of Siena yet feeling so removed from everything. I highly recommend staying here!"
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Cozy cottage with pool 10 km from Siena
Outdoor dining

Cozy cottage with pool 10 km from Siena

Cozy cottage with pool 10 km from Siena
Charming apartment in the Historic Center of Siena
TV, books

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (18)
"Great apartment. Easy access to the train/bus"
Charming apartment in the Historic Center of Siena
HOUSE WOW panoramic terrace *.*
Outdoor dining

HOUSE WOW panoramic terrace *.*

10.0 out of 10, Exceptional, (20)
"So happy we chose this property. A wonderful home away from home, so close to everything, enchanting terrace/views, and superb communicative hosts. "
HOUSE WOW panoramic terrace *.*
Amazing home in Siena with WiFi
Fridge, oven, stovetop, dishwasher

Amazing home in Siena with WiFi

10.0 out of 10, Exceptional, (1)
"In accordance with our expectations."
Amazing home in Siena with WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siena Hotel Reviews

Four Points by Sheraton Siena

Four Points by Sheraton Siena

10/10 Excellent
"Comfortable rooms, excellent breakfast, lovely pool, and service!"
Anonymous traveller 2-night trip
Posted 3 days ago
Four Points by Sheraton Siena