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House vacation rentals in Montescudaio

Find and book unique houses on Airbnb

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Popular amenities for Montescudaio house rentals

House rentals with a pool

Guest favorite
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars1 month ago
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!
Top guest favorite
Home in Lucca
5 out of 5 average rating, 115 reviews

Il Bambu (with private swimming pool)

JannigjeRating, 5 stars2 weeks ago
We had a fantastic time at Nadia's place. The view is stunning and a very nice swimming pool that is well maintained by Giacomo. Very friendly welcome and received tips to do in the area. Good location near Lucca and in a nice green area. We would book this again.
Top guest favorite
Home in Bagno A Ripoli
4.95 out of 5 average rating, 139 reviews

Casetta Melograno – Cozy farmhouse in Chianti

JacobRating, 5 stars4 days ago
I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.
Guest favorite
Home in Colle di Val d'Elsa
4.94 out of 5 average rating, 64 reviews

Countryhometuscany - House with Garden -

GabrielleRating, 5 stars1 week ago
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.
Top guest favorite
Home in Volterra
4.93 out of 5 average rating, 180 reviews

Collina Power

DeanRating, 5 stars3 weeks ago
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!
Guest favorite
Home in Fibbiano
4.96 out of 5 average rating, 148 reviews

House in Tuscany with pool

RobertRating, 5 stars3 weeks ago
Cristina is the perfect host and the house is beautiful. The surroundings are amazing and the views......wow! All through the booking and our stay there Cristina was swift to answer any questions we had and also was happy to offer suggestions on places to go and where to eat. We had a perfect week there and I wouldn't hesitate to go back or to recommend her place to anyone else. Cristina and her sister met us at the house and showed us round, clearly pointing out all the relevant bits that we would need to know. Thank you so much for making our week in Italy so special and enjoyable......we are already looking to come back!
Guest favorite
Home in San Gimignano
4.98 out of 5 average rating, 45 reviews

La Moraiola - Characteristic Tuscan barn

MaryRating, 5 stars1 month ago
I took this trip with my sister to San Gimignano and it was absolutely incredible! The views from Egizia’s house were just stunning and breathtaking! From the beginning Egizia was very easy to get into contact with about any questions that I had. She gave wonderful recommendations and booked everything for me! We went to a winery that she had suggested and it was great! The Pilates instructor Giulia was also amazing! And with the hills as our scenery it was such a cool and incredible experience! My sister and I had so much fun! This was an unforgettable trip! We’ll definitely have to come back again!
Guest favorite
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 68 reviews

Chianti House Stunning view 20 min. from Florence

AshlynnRating, 5 stars8 months ago
What a place! An absolutely perfect little hideaway in an absolutely gorgeous location. This charming abode has exactly what you need to completely escape and soak in the stunning surroundings of the Tuscan landscape. Even though it rained quite a bit of our visit, sitting on the veranda overlooking the pool and rolling hills nice and dry under the tent was magical - the lush view could never get old! The stone space is as quiet and cozy as can be - comfortable bed and couch, very functional kitchen, nice bathroom. Pretty antiques make the space homey. My husband even jumped in the very cold pool in the rain and now we want to come back in the summer sun to enjoy it more. Tommaso was incredibly sweet and offered recommendations and walked us through the whole place upon check in - and he was kind and responsive the whole time. Really can’t recommend this experience enough!

Weekly house rentals

Top guest favorite
Home in Montecatini Alto
5 out of 5 average rating, 32 reviews

Montecatini Alto Art View

GarethRating, 5 stars2 days ago
We loved staying in Carolina’s house in Montecatini Alto. It was a lovely welcoming place to wake up in and return to at the end of the day. The view from the windows and the patio is extraordinary and sitting out enjoying it was one of the best parts of the holiday. The house had all we needed. Carolina was a wonderful host; friendly, quick to reply and extremely helpful. The village is a lovely quiet place to stay and we wouldn’t look anywhere else if we return to the area.
Superhost
Home in Chianni
4.83 out of 5 average rating, 59 reviews

Three bedroom historical house with the best views

LaurenRating, 5 stars3 weeks ago
We loved our stay here! The house and the views were truly as picturesque as it seems in the photos. A dream spot! The town itself is full of local flair and is beautiful too. Not touristy at all. Close enough to nearby towns though to explore more of Tuscany! Overall a great stay and Laura was a kind and responsive host.
Top guest favorite
Home in Palaia
4.98 out of 5 average rating, 44 reviews

Conte Martini House

NicolasRating, 5 stars1 week ago
Wonderful place to either lay back and enjoy the picturesque-postcard view from the comfort of your front yard or the pool (which was refreshingly cool in June), or to go further explore Tuscany locations within reach. The house was beautiful, clean and equipped with everything you could ask for, ie a quiet and air conditioned bedroom, kitchen with a gas stove, fridge and a wood fired bbq and a jacuzzi + comfy seating outside. Shops, restaurants and bars are all within walking distance, max 10 minutes. Andrea is a fantastic host who clearly cares about providing the best possible stay for her guests, which she did. Whenever we return to Tuscany, we will definitely make sure to stay here at Palaia again.
Top guest favorite
Home in Castellina Marittima
5 out of 5 average rating, 15 reviews

Iris Residence "Casa vista mare-giardino-piscina"

ValentinaRating, 5 stars1 week ago
Our stay at Dario's house was just perfect! The apartment is stylishly decorated, beautiful and equipped with everything you need. Particularly impressive was the private pool – an absolute oasis of well-being! 🏊‍♂️✨ Everything was extremely clean and tidy, which immediately gave a pleasant feeling. Privacy was absolutely given, and yet Dario was incredibly helpful when we needed anything. His hospitality was great – friendly, attentive and present in just the right measure! 😊 An all-around great stay – we will definitely be back! 🌟
Top guest favorite
Home in Poggibonsi
4.92 out of 5 average rating, 59 reviews

Agriturismo Podere San Martino (apartment for two)

LukasRating, 5 stars4 weeks ago
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!
Guest favorite
Home in Montecatini Val di Cecina
4.88 out of 5 average rating, 16 reviews

Stunning Casa with Pool & Views

RobinRating, 5 stars8 months ago
We loved the peaceful environment and the home itself. We were close to restaurants and grocery stores.
Guest favorite
Home in Crespina
4.98 out of 5 average rating, 84 reviews

"IRIS" Secret Nature Retreat

Lou LenaRating, 5 stars1 month ago
The place is great! Great view, really quite & close to nature :) Giorgio & Carmen were great hosts & also had a guide for the region. Excellent, thank you for everything! :)
Top guest favorite
Home in Provincia di Livorno
5 out of 5 average rating, 20 reviews

Dalu Home

JessicaRating, 5 stars2 weeks ago
Staying in this apartment was wonderful. My boyfriend and I spent two nights immersed in the Tuscan countryside in a small cozy apartment, very clean and equipped with everything you need. The garden is beautiful, full of fruit trees and sweet cats that enrich the living room. We will soon return to visit Sheila in her lovely country home.

Private house rentals

Top guest favorite
Home in Castagneto Carducci
5 out of 5 average rating, 13 reviews

"Il Frassino" Country House

ManuelRating, 5 stars1 day ago
Our stay was perfect all around! We immediately felt at home. The accommodation is not only convincing because of the great location and surroundings, it was also wonderfully furnished and there was nothing missing. We would like to emphasize the warm hospitality of Ranieri. He was always available and helpful. We would come back.
Top guest favorite
Home in Siena
5 out of 5 average rating, 13 reviews

10 min from the Center | La Capanna di Franco

JasonRating, 5 stars2 weeks ago
Beautiful location and surroundings. Wish we had known just how beautiful it was. We would have spent more night there for sure. Highly Recommended. A+++++
Guest favorite
Home in Greve in Chianti
5 out of 5 average rating, 61 reviews

La Loggia – Casine al Sole

PeterRating, 5 stars1 month ago
Spontaneously booked. And can easily arrange everything necessary at short notice. Federico is calmly communicative and can refine the stay with good recommendations. The location is special. The place has a good effect on the body and mind. WeiläuAbout but not far for shopping or restaurants. A beautiful pool. Tasteful spaces. Wifi junckies could sometimes hate something with the net, but the overall picture is not diminished. Everything else necessary is on site or will be promptly provided by Federico. A wonderful starting point for Visit in Florence or Chianti. Lots of rustic trattorias,winemakers and olive farmers nearby.
Superhost
Home in Mazzanta
4.89 out of 5 average rating, 35 reviews

A STONE'S THROW FROM THE SEA

AdrianRating, 5 stars8 months ago
We were 2 and a dog there for a week. The apartment is rather small, but the outdoor area is large and fenced. Andrea showed us everything and gave good tips for the area. You should be well spread on mosquitoes, but even there Andrea had a starter set😏 ready.
Guest favorite
Home in Castiglioncello
4.89 out of 5 average rating, 57 reviews

Casa Le Forbici. Private access to the sea

ScottRating, 5 stars1 month ago
we absolutely loved our stay… just as described and more… close to Florence and other spots… what a view!!! Hopefully be back!
Guest favorite
Home in Cecina
4.85 out of 5 average rating, 139 reviews

Cottage in the Cecina countryside

KatharinaRating, 5 stars1 week ago
Our stay at Fernanda's house was very nice. The place looks like the photos. You are absolutely private, despite the proximity to the host's house. The street is close but did not bother us at all. There are hardly any cars there at night. The house is small but nice, you have everything you need and a wonderful terrace with garden. You have to get used to the shower for a short time, but that's also quick. We rented bicycles in the village and were able to ride to the beach or the village quickly and easily. Great starting point for excursions in the area. Fernanda also gave us a great restaurant recommendation for our wedding day (thank you again, it was so beautiful!!) and there was a homemade cake. Fernanda and her husband are incredibly warm and helpful. They can only speak Italian, but thanks to modern technology, it is also not a problem if you do not understand everything. We highly recommend the house and would book it again at any time!!
Guest favorite
Home in Vinci
5 out of 5 average rating, 11 reviews

Il Palagio

MohammadRating, 5 stars3 weeks ago
Outstanding accommodation. Pristine, spacious yet very cozy. Very helpful host. 10/10 would come again
Superhost
Home in Gambassi Terme
4.68 out of 5 average rating, 71 reviews

Corbezzolo stone cottage, Mummialla

DanielRating, 5 stars9 months ago
A very nice quiet place! Too bad it wasn't very nice and hot during our stay, but we still bathed and enjoyed the wonderful view! Consider bringing mosquito hunting, as there are many. We would go back tomorrow morning if we could:)

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Pisa
  5. Montescudaio
  6. House rentals