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Apartment holiday rentals in Province of Siena

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Popular amenities for Province of Siena apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Siena
4.93 out of 5 average rating, 148 reviews

Sergio's House

VáninaRating, 5 stars3 weeks ago
Amorosa Marta and her dad, always attentive. Siena is beautiful and the location is fantastic. To park from 8 to 20 you have to pay parking, if not 40€ fine. Marta answered the question of where to pay. The truth, highly recommended !
Guest favourite
Flat in Siena
4.93 out of 5 average rating, 188 reviews

HOUSE OF THE MADONNA

IdinRating, 5 stars5 days ago
Amazing host! So nice and personable! I 100% recommend them!
Guest favourite
Flat in Siena
4.94 out of 5 average rating, 178 reviews

Casa Fusari - Apartment next to the Duomo

KatieRating, 5 stars1 month ago
This is our second time in this lovely apartment and we wouldn’t have a second thought of making our third time. Silvia and Tomasso always respond promptly when messaged and always make sure all is well! Ci vediamo, Katie.
Top guest favourite
Flat in Montepulciano
5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

MarkRating, 5 stars3 weeks ago
My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!
Top guest favourite
Flat in Barberino Val d'Elsa
4.99 out of 5 average rating, 120 reviews

Apartment in Chianti at Mulino dell 'Argenna

SophieRating, 5 stars6 days ago
We had a lovely stay! Elisa and Alessandro are so kind and very helpful with anything we needed. They made a reservation at a restaurant for us when everything was fully booked. Thank you for your great hospitality!
Top guest favourite
Flat in Montepulciano
4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

AliciaRating, 5 stars2 weeks ago
We had a wonderful stay at Luca’s and the view cannot be beat! Luca went above expectations by meeting us at checkin to show us where to park and taking our luggage to and from the unit. Hope to stay here again one day!
Guest favourite
Flat in Siena
4.86 out of 5 average rating, 43 reviews

Fine house with altana and panoramic terrace

JohnRating, 5 stars10 months ago
This was one of the most amazing Airbnb properties I've ever had the pleasure in experiencing. It's a penthouse apartment overlooking the tiled rooftops of Siena, with a view straight across to the famous church tower. Taking your morning coffee here with the pigeons is one of the most serene things you could imagine. Pure Italy. There's also a rooftop garden we could pull fresh cherry tomatoes and basil from for our cooking. It's located literally a 3-minute walk from the main piazza, and in the middle of all Sienna's shopping, walking, and dining attractions. Nicoletta was patient with our travel schedule, and met us on the later side of our check-in without a problem.
Guest favourite
Flat in Monticchiello
4.97 out of 5 average rating, 151 reviews

Casa Bonari - a paradise for the eyes

HopeRating, 5 stars2 weeks ago
If you are seeking a bit of Tuscan heaven... this might be the place for you!  The family owners are caring, thoughtful & engaging.  They are proud to share this family built & adored home with guests from all over the world.  It is bright, clean & full of charm.  It is as much a retreat as the setting it sits in.  We felt right at home among the beautiful olive trees, bird songs & children at play.  Casa Bonari is a place to return to again & again for respite, joy & simplicity. It is sweetly etched upon our hearts.

Private apartment rentals

Top guest favourite
Flat in Siena
4.98 out of 5 average rating, 94 reviews

CASA WOW panoramic terrace * . *

JulieRating, 5 stars1 month ago
What an amazing place to call home for the 4 nights we stayed! The apartment is beautiful, clean, has absolutely everything you could possibly need, is steps away from so many things to see, and has the best patio and view one could hope for. Emanuela and Francesca are extremely kind, caring and helpful, even helping us find restaurants (and make reservations) and find a local business to help with my husband’s work while we were in Siena. Outstanding stay! Book now: you will not regret it!
Top guest favourite
Flat in Siena
4.97 out of 5 average rating, 159 reviews

Casa Tecla at the City Walls

JerômeRating, 5 stars3 weeks ago
Good location thanks to the escalators for easy access to the historic center. Listing as described and photos. Barbara is very responsive and friendly.
Top guest favourite
Flat in Siena
4.92 out of 5 average rating, 71 reviews

Apartment in the historic center of Siena

SeanRating, 5 stars1 month ago
A really incredible apartment to stay at while in Siena. Really thoughtfully designed and the view is even better in person. You gotta do the early morning wake up for sunrise! Super responsive and helpful communication as well. 11/10 - strongly recommend.
Top guest favourite
Flat in Siena
4.97 out of 5 average rating, 32 reviews

Palazzo del Papa Standard Suites

TravisRating, 5 stars2 weeks ago
AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.
Top guest favourite
Flat in Poggibonsi
4.97 out of 5 average rating, 253 reviews

OLIVE TREE APARTMENT - CHIANTI

AnnaRating, 5 stars1 week ago
What an incredible stay at this beautiful apartment! Pictures don’t do it justice. A true Tuscan paradise. Apartment is spotless. Beautiful touches everywhere and very spacious. The views are incredible. Great front and back porches to relax and take in the beauty. Mario and Nadia are wonderful hosts. Always responsive and a pleasure to interact with. Loved our stay and would definitely come back again. Highly recommend!
Guest favourite
Flat in Siena
4.97 out of 5 average rating, 30 reviews

Casa Duprè - Cozy Apartment near Piazza del Campo

KarenRating, 5 stars8 months ago
Great apartment! It is very spacious, clean, well illuminated, excellent location and very comfortable. The view from the bedrooms is fantastic! Dario and his team were incredible hosts. They were always very responsive. They were very helpful and quick to respond to any questions and offered lots of valuable, practical tips and suggestions on things to do and where to visit during our stay. Dario and the team made our stay a 5 star experience; they were insightful and very kind! Thank you.
Guest favourite
Flat in Siena
4.93 out of 5 average rating, 71 reviews

Palazzo Rinuccini Torre

Patricia MazzoniRating, 5 stars1 month ago
This place is simply fantastic! Best I've ever stayed in Italy!!!! Beautiful, new in the interior without losing the feeling of being in Siena, decoration of very good taste, discreet, clean, comfortable and elegant. All house equipment in perfect condition, clean, available and easy to access. Enxoval of good quality and very clean, flawless toilets, delicious showers!! Definitely note mil!
Top guest favourite
Flat in Siena
4.98 out of 5 average rating, 92 reviews

Luxury frescoed apartment in the historical center

BethRating, 5 stars3 weeks ago
We had a wonderful stay! The home is stunning. It was like staying in a beautiful museum. There were seven adult family members and there was plenty of space for all. The location was terrific - near the center of the beautiful city of Siena! As a bonus, Bianca is a professional photographer and took formal engagement photos of my daughter and her fiancé. That was great!

Apartment rentals with a hot tub

Guest favourite
Flat in Pogi
5 out of 5 average rating, 12 reviews

Borgo Iesolana Family Suite Olivi

LianaRating, 5 stars1 week ago
This Borgo Iesolana resort in Tuscany is absolutely beautiful! 😍 The views are incredible and it’s very relaxing. The restaurant also had some yummy food. Our family loved this place! Definitely recommended!
Superhost
Flat in San Giovanni d'Asso
5 out of 5 average rating, 19 reviews

Podere Ferranino #Cimabue Townhouse

CarolynRating, 5 stars12 months ago
Great location for exploring the beautiful countryside of southern Tuscany. Accommodation was great and the pool was lovely. We visited Siena, Montepulciano, Pienza and San Quirico d’Orcia and the warm waters at Terme San Filippo We would definitely recommend the Coop in Torrenieri just 10 mins in the car, a bit tricky to find but has all that you need.
Guest favourite
Flat in Seggiano
4.88 out of 5 average rating, 64 reviews

Romantic farmhouse, garden apartment with panorama

G.Rating, 5 stars1 month ago
Beautiful place with a breathtaking view, truly romantic garden, and cozily furnished apartment to relax after a stroll through the Tuscan hillside. Thank you for a wonderful vacation.
Guest favourite
Flat in Montevarchi
4.91 out of 5 average rating, 104 reviews

Apartment with garden in the heart of Tuscany

Mary BethRating, 5 stars7 months ago
Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!
Top guest favourite
Flat in Siena
5 out of 5 average rating, 6 reviews

The Tower [Central Course]

AndreaRating, 5 stars1 month ago
Tommaso’s home is absolutely stunning. Also very comfortable and conveniently located in the heart of Siena’s historic center. Tommaso was easy to communicate with and always very responsive. Lovely place
Guest favourite
Flat in Monteroni d'Arbia
4.95 out of 5 average rating, 65 reviews

San Giovanni in Poggio, Crepuscolo app. 60 sqm

ŁukaszRating, 5 stars1 month ago
Marvelous place, Sara is very friendly and helpful host. Can’t wait to visit this place again.
Top guest favourite
Flat in Montepulciano
4.92 out of 5 average rating, 142 reviews

Charming House in Montepulciano

KirstenRating, 5 stars2 months ago
Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!
Guest favourite
Flat in Siena
4.87 out of 5 average rating, 23 reviews

Apartment in a Villa, Siena: swimming pool, relax

JohnRating, 5 stars8 months ago
Our stay was amazing. The villa was as advertised and more. Quiet, clean, beautiful setting, and walking distance to the heart of Sienna. It was great to have off street parking, so no hassles at all. The walk to Piazza de Campo was only 15-20 minutes, with a little bit of an up hill climb at first, but no big problem. We would highly recommend staying here.

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