Siena Vacation Rentals

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Siena Vacation Homes

Beautiful stone house with garden and private pool.
Escape to a serene garden setting with a charming stone building, surrounded by lush flowering plants and a meandering stone pathway.

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (62)
"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.
Il Palazzetto
Relax in this open-plan living area with a patio offering a serene view of lush green surroundings.

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto
Villa Le Tortore Tuscany private luxury pool relax
Relax by the pool surrounded by a lush olive tree and comfortable seating.

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (89)
"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
Experience the perfect blend of architecture and outdoor living with a brick facade, large windows, and comfortable seating areas.

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
Relax by the tranquil pool surrounded by lounge chairs and a permanent structure.

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!
Relax by the serene pool surrounded by lush greenery and comfortable deck chairs.

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
Archways and brick columns frame this spacious room with a high ceiling, perfect for showcasing artwork or photography.

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
Relax by the serene pool surrounded by lush greenery and breathtaking views.

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
Enjoy a stylish space with a dining area, living room, and kitchen, featuring a sofa, metal table, and oven.

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
Relax by the serene pool surrounded by lush greenery and trees, with lounge chairs and umbrellas providing shade.

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
detached villa with private pool and garden
Relax by the serene pool surrounded by lush greenery and rolling hills.

detached villa with private pool and garden

8.8 out of 10, Excellent, (23)
"Good location to the town and lovely garden space"
detached villa with private pool and garden
L'Oliviera by Interhome
Enjoy al fresco dining in a serene garden setting surrounded by lush greenery and a tall cypress tree.

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
Enjoy a casual meal in our garden courtyard, surrounded by lush greenery and a stone wall.

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
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
Chianti Classico Home Panoramic View, Castellina in Chianti, Italy
Enter a cozy living space with a sofa, table, and chandelier.

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
Enjoy a classic design with a high ceiling, comfortable seating area, and city views.

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
Capanna, Typical Tuscan Farmhouse With Fruit Garden
Relax in a serene outdoor space with a stone building, lounge chairs, and lush greenery.

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
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Escape to a serene outdoor oasis with a picnic table nestled under a vine-covered pergola, surrounded by lush greenery and a tranquil view.

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
HOUSE WOW panoramic terrace *.*
Enjoy breathtaking views of the historic church and its bell tower from this outdoor space.

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 *.*
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Relax by the serene pool surrounded by lush greenery and a natural stone patio.

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
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 Athena

Hotel Athena

10/10 Excellent
"Staff was incredible - 10 minute walk to everything. Highly recommend! Especially loved front desk crew and Robert in the restaurant. "
Jenn 1-night trip
Posted 1 day ago
Hotel Athena