Siena Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Siena Vacation Homes

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
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Outdoor pool

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (25)
"Lovely place, lovely people, lovely environment "
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Outdoor pool

Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

9.6 out of 10, Exceptional, (32)
"Renting this villa was a relaxing, enjoyable way to experience Siena and the surrounding countryside. Lovely pool and grounds."
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Farmhouse in old mill nestled in the beautiful Chianti hills
Interior

Farmhouse in old mill nestled in the beautiful Chianti hills

8.6 out of 10, Excellent, (17)
"A beautiful place to stay and very friendly hosts; Roberto and Rafaella will do anything to make your stay unforgettable. The house has everything you need and the pool is nice and beautiful. Lots of nice places to visit in the neighbourhood. I can surely recommend this Farmhouse!!!!"
Farmhouse in old mill nestled in the beautiful Chianti hills
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
Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION
Smart TV, books

Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION

10.0 out of 10, Exceptional, (21)
"Location, apartment, host all top notch! Will stay again next time we are in Siena! Everything you need and in a fantastic central location."
Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION
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 crib

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 CA $208
CA $262 total
includes taxes & fees
Sep 1 - Sep 2
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
Capanna, Typical Tuscan Farmhouse With Fruit Garden
Property grounds

Capanna, Typical Tuscan Farmhouse With Fruit Garden

10.0 out of 10, Exceptional, (67)
"Loved our stay the host was fantastic and the property is beyond beautiful. This is a type of place that has spectacular views and a magical atmosphere."
Capanna, Typical Tuscan Farmhouse With Fruit Garden
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

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Great hotel and lovely staff in a perfect location. Will book here again next time in Siena "
David 2-night trip
Posted 2 days ago
Hotel Chiusarelli