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Condo holiday rentals in Province of Siena

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Popular amenities for Province of Siena condo rentals

Weekly condo rentals

Superhost
Condo in Pergine Valdarno
4.81 out of 5 average rating, 16 reviews

Relaxing holiday, 5 apts +pool among the vineyards

FelixRating, 5 stars8 months ago
Beautifully located domain near the tiny Pieve a Presciano with a beautiful view of the village and the surrounding cypresses. The pool is the great asset of this accommodation, cleanly maintained and very large. Furthermore, basic equipped and typical Tuscan, but everything you need is present.
Top Guest favourite
Condo in Siena
5 out of 5 average rating, 35 reviews

Top Apartment Palazzo Tufi with Garage, out LTZ

AndreaRating, 5 stars2 days ago
Great apartment in a fabulous location. Francesco is very helpful and gave great recommendations. Would not hesitate to stay here again. Grazie
Top Guest favourite
Condo in Poggibonsi
4.95 out of 5 average rating, 77 reviews

Gallery Apartment near Chianti

ChrissyaniaRating, 5 stars6 days ago
Kind host, spacious space and very clean!
Guest favourite
Condo in Piazze
4.95 out of 5 average rating, 20 reviews

Canonica, Camporsevoli.

NikolajRating, 5 stars8 months ago
No other than Amazing! A hidden gem in the heart of Tuscany. Never have we felt so truly welcome and almost part of the family from day 1. Stunning views from the apartment windows, beautiful and authentic furnitures and cool rooms in the tuscan heat. Many, many, many recommendations from the whole family!❤️
Superhost
Condo in San Gimignano
5 out of 5 average rating, 4 reviews

Apartment Melissa

StéphanieRating, 5 stars81 months ago
We stayed in the Melissa apartment and it was great, very spacious and bigger than expected. The apartment is self-catering and has all that you need to cook and have a great time. There is no terrace for this apartment, but they are many areas around the property that allow for some outdoor time. The location was beautiful, amazing views, great swimming pool and an overall very relaxed place. The property is 15 mins away from San Gimignano and very close to the bigger towns/villages to visit. Having a car is a must. The staff, the welcome and overall communication was lovely and easy, I would definitely recommend staying here.
Top Guest favourite
Condo in Siena
4.86 out of 5 average rating, 343 reviews

Apartment in the heart of Siena

GiedreRating, 5 stars5 months ago
The suite matched the description and photos. Very convenient location - both sights and train station within easy walking distance, right outside the bus stop. Clear check in instructions, hosts send a lot of helpful tips and recommendations of places to visit. The suite maybe a little dark, the windows go out to the backyard, but you can't hear the street noises behind you. We had a good time and we loved it.
Guest favourite
Condo in Castellina in Chianti
4.79 out of 5 average rating, 323 reviews

relaxation among the vineyards of Chianti1-IlVillinoFarmhouse

JasonRating, 5 stars3 weeks ago
It was a comfortable setting, beautiful scenery, we had a good Tuscany, looking forward to be back again
Guest favourite
Condo in Poggibonsi
4.93 out of 5 average rating, 41 reviews

Charming apartment in Tuscany

MichelleRating, 5 stars6 months ago
The hosts were incredibly friendly and understanding, they were also very good with communication!

Pet-friendly condo rentals

Guest favourite
Condo in Arezzo
4.98 out of 5 average rating, 41 reviews

'Mediterraneo' Cozy two-room apartment with garden

RobertoRating, 5 stars3 months ago
Niceapartment, comfortable and very equipped. Ideal for those with a dog. You can get to the city center on foot. Friendly and helpful host.
Guest favourite
Condo in Arezzo
4.86 out of 5 average rating, 92 reviews

Il Piccolo Ristoro

BRating, 5 stars3 weeks ago
A great place to stay when are in Arezzo. Property is all single owned and even has side yard &. some backyard...In the middle of the city! Sure, its a 10-12 min brisk walk into the heart of downtown. But that's what makes this place special & quiet. Hosts were very helpful in connecting one of our group to local wine tasting room who assisted us in setting up some self-drive tasting adventures. A another in our group asked for a few things which could not found in apt, and host responded in minutes. We can't really say anything bad the apt or host re our 7nht stay.
Guest favourite
Condo in Arezzo
4.76 out of 5 average rating, 29 reviews

Cozy house in the vineyard -Fogliadalloro-

LeonardoRating, 5 stars3 months ago
quiet place for both us and our dog who immediately made friends with the host's 2 dogs (Bretta and Charly)❤️❤️❤️, we will be back as soon as possible!!!
Top Guest favourite
Condo in Siena
4.96 out of 5 average rating, 166 reviews

Elegant vintage decorated home in the old Siena

AntonioRating, 5 stars3 days ago
Great welcome and the stay was comfortable and equipped at a price paid. Everything the apartment was perfectly heated as per my request. I particularly appreciated the Falomo memory mattress that I found of high quality. I highly recommend this apartment to have a nice experience in Siena .
Superhost
Condo in Arezzo
4.91 out of 5 average rating, 33 reviews

Cozy bright accommodation near downtown

EmanueleRating, 5 stars4 months ago
Long weekend spent in tranquility a short distance from the center. Very quiet and family friendly area, very clean and tidy house, equipped as if lived daily. A nice walk takes you to the historic center. We had a great time and if we return to Arezzo we will definitely contact Silvia, whom I thank for the sheep kinder for my two girls, sometimes small gestures make a difference. Have a great life!
Superhost
Condo in Laterina
5 out of 5 average rating, 3 reviews

Le Fornaci Holiday Home - Dondo Apartment

ManuelaRating, 5 stars4 months ago
We've been guests to six people. When we arrived in the evening, the apartment was as described, well heated and comfortable The staff is courteous, kind and always available. We had dinner in their restaurant, high quality cuisine at affordable prices. Repeat experience
Guest favourite
Condo in San Gimignano
4.82 out of 5 average rating, 221 reviews

Historic centre - cozy apartment

CristinaRating, 5 stars2 weeks ago
This was my partner and I’s second time staying in this apartment with Federico and Helga and it was just as the first time - 5 stars all around! The apartment is perfect, the location is accessible to everything but is also peaceful and quiet and Federico is very kind and helpful. I would absolutely stay a third time!
Superhost
Condo in Siena
4.81 out of 5 average rating, 279 reviews

Liberty Siena Flat (New Apt 2)

LucyRating, 5 stars1 month ago
Super clean, easy check-in and check-out, great location, in the city's heart, and a short walk to everything! As a woman in her 20s, I stayed alone and felt safe and secure. Would recommend!

Condo rentals with a pool

Superhost
Condo in Cavriglia
4.88 out of 5 average rating, 146 reviews

Chianti La Pruneta, Michelangelo apartment.

JessRating, 5 stars5 months ago
Thanks for a fantastic few days Massimo! I don't think we could have picked a better place for our Tuscany holiday. The view of the valley was beautiful and the apartment was the perfect size for us two! The cooking class was amazing and we really loved the wine tasting at the local wineries as well.
Superhost
Condo in Radda in Chianti
4.83 out of 5 average rating, 83 reviews

💜 "Gaia" at Podere Le Fontanelle

SantiagoRating, 5 stars3 months ago
Amazing location, near to multiple restaurants. The place was very nice, overall an amazing experience !
Top Guest favourite
Condo in Pieve Vecchia
4.93 out of 5 average rating, 46 reviews

Ebe Rooms - La Cruna Apartment

ElenaRating, 5 stars6 months ago
Gorgeous tranquil place, divine swimming pool and lovely hosts. Would love to stay again!
Superhost
Condo in Montefollonico
4.88 out of 5 average rating, 57 reviews

Il Chicchino, Swimming Pool, Tennis, Wi-Fi, Park

NectariosRating, 5 stars4 months ago
We thoroughly enjoyed our stay at Daphne's place. It is set amongst beautiful manicured gardens, a large pool (which was covered due to seasons end), a tennis court and the views across the Tuscan landscape are incredible. The apartment itself was immaculate and looked better than the photos. It is well appointed, spotlessly clean and modern. We found Montefollonico to be quieter than other tourist destinations and it's a short walk/drive from the residence. It too is beautiful and charming. There's only one Grocery store specializing in Tuscan products and more, It catered for pretty much all we needed. There's also a pharmacy, a quaint bar and a restaurant that was surprisingly good, and the owner is quite the character, in a good way :). Montepulciano is a short 15 or so minute drive away. Having a car is a must unless you just want to spend quality time away from everything and relax in a most beautiful, tranquil and private setting. Thank you Daphne, we loved our stay.
Superhost
Condo in San Gimignanello
5 out of 5 average rating, 5 reviews

Il Loggiato, 2 bedrooms with a view

LaurenRating, 5 stars6 months ago
Stunning place. Loved the vineyard, olive trees and pool. Exactly what I was looking for in a Tuscan experience!!
Guest favourite
Condo in Castelnuovo Berardenga
4.91 out of 5 average rating, 35 reviews

Beautiful countryside annex with swimming pool!

YoavRating, 5 stars7 months ago
Our stay at Fiamma's agritourism farmhouse near Siena was absolutely incredible. The location is like something out of a dream—surrounded by stunning landscapes that make you feel like you're in a postcard. The house itself is beautiful, with cozy, well-appointed rooms that made us feel right at home. Our kids had a blast, especially with the swimming pool overlooking vineyards, which was perfect for relaxing after a day of exploring the Tuscan countryside. Fiamma and her husband were fantastic hoss, always making sure we had everything we needed. We couldn't have asked for a better experience, and we can't wait to return
Top Guest favourite
Condo in Barberino Tavarnelle
5 out of 5 average rating, 27 reviews

Entire house for couple with exclusive pool

RussellRating, 5 stars6 months ago
The highlight of our tour around Italy, simply stunning. The outside area is the obvious highlight; the lovely pool overlooking iconic Tuscan scenery, but the inside is also perfect (didn’t think we’d fully use the two bathrooms but we did!!!). Matteo was a great host and couldn’t do enough for us - he even led the way in his car to help us find the restaurant he’d recommended when we arrived (one of our best meals of our holiday). A truly magical stay.
Guest favourite
Condo in Castiglioni
4.91 out of 5 average rating, 100 reviews

[Ninfea] Ancient House in Tuscany

NikiRating, 5 stars5 months ago
Wish we could’ve stayed here longer! Gorgeous location and lovely interior. The bathroom was amazing. Such a nice stay!

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