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House vacation rentals in Montespertoli

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Popular amenities for Montespertoli house rentals

House rentals with a pool

Superhost
A large outdoor swimming pool is visible under a clear blue sky, surrounded by lush greenery. The tranquil water reflects the sunlight, creating a calming atmosphere. Vegetation frames the scene, enhancing the privacy of the pool area.
Home in Montespertoli
4.84 out of 5 average rating, 75 reviews

Vacation immersed in the Tuscan countryside 'Canaiolo'

FedericaRating, 5 stars1 week ago
Heaven is a place on Earth
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 71 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 days ago
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Superhost
A charming stone farmhouse is set against a backdrop of green hills. The exterior showcases rustic features, including wooden shutters and a tiled roof. A pathway leads to the entrance, bordered by lush greenery and flowering plants, creating a serene environment.
Home in Figline Valdarno
4.96 out of 5 average rating, 107 reviews

The Owl: view, pool and garden

StephenRating, 5 stars3 weeks ago
We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki
Top guest favorite
A rustic dining area is highlighted by a long wooden table surrounded by several chairs. A vase of sunflowers sits at the center. The stone wall adds warmth to the space, while a clock and decorative items provide an inviting touch.
Home in Bagno A Ripoli
4.95 out of 5 average rating, 137 reviews

Casetta Melograno – Cozy farmhouse in Chianti

LeonieRating, 5 stars6 days ago
Sonia and her family are all so nice! We felt very comfortable in this very beautiful appartement. The view is amazing! We loved the toskany landside with good wine, oliveoil and beautiful nature. Thank you for everything!
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Guest favorite
A stone pathway leads to a charming rustic building, surrounded by greenery and blooming flowers. To the side, a flat stone table under a large tree provides a serene outdoor space, inviting relaxation amidst nature.
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars2 weeks ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!
Guest favorite
Two lounge chairs made of natural wood are positioned on a deck. A small table holds two glasses overlooking rolling green hills and vineyards under a clear blue sky. The landscape extends into the distance, providing a serene rural view.
Home in Montespertoli
4.92 out of 5 average rating, 26 reviews

Villa Tirinzano for 14 guests with private pool

Lars PederRating, 5 stars6 days ago
We had an amazing week at Villa Tirinzano! The villa itself is located at the end of a dirt road with a few minor holes in it, so beware of that before driving to the villa for the first time. The car will accumulate some road dust along the way, but that didn’t matter much to us. The property is large and really well maintained, both inside and outside. The building is rustic and beautiful, and the standards definitely met our expectations. Being a group of four different families, it was great that the villa is divided into four separate apartments with own bathrooms. This allowed for some personal space. Outside there’s lots of beautiful flowers, trees and plants, and the view over the Tuscan hills is amazing. The pool area was top notch. We especially enjoyed the ping pong table near the pool area. Agnese and her family were really gracious hosts, and communicating with her was easy and efficient. We would love to come back, and can definitely recommend it to everyone!
Guest favorite
A rectangular private pool is surrounded by a grassy area and olive trees, providing a serene outdoor setting. Six lounge chairs are placed neatly around the pool, offering space for relaxation. The sky is partly cloudy, enhancing the natural beauty of the surroundings.
Home in San Miniato
4.92 out of 5 average rating, 101 reviews

Lovely house in a scenic and paiceful location

CedricRating, 5 stars5 days ago
We stayed at Maria’s home for a long family weekend with 6 adults. There is quality ac, 3 bathrooms and 3 good double beds. The private pool is very good with comfortable lounge chairs. Cooking easy in the fully equipped kitchen. Recommended!

Weekly house rentals

Guest favorite
A clear swimming pool is surrounded by well-maintained greenery, featuring lounge chairs with umbrellas for shade. The pool area offers a relaxing atmosphere, with sunlight filtering through the nearby trees, creating a serene outdoor space.
Home in Montelupo Fiorentino
5 out of 5 average rating, 5 reviews

Villa Le Masse - La Torre Residence

GitteRating, 5 stars2 days ago
Thank you for a wonderful stay. Lovely cooling pool, private area. Very beautiful surroundings with vineyard as a neighbor. Great hiking and biking routes just outside the area. Car is required when shopping or visiting small towns and restaurants. You can easily bike around both on bike paths and roads. We used the good recommendations the hosts gave us, not least led to very good restaurant visits. The beds are good, very nice quality bed linen. When we arrived at the road leading up into the hills to the property, we were guided by the hosts who drove in front of us. Otherwise, it would probably have been hard to find. Thanks for that. We can only send a lot of great recommendations for this place. Thank you🤩❤️
Guest favorite
A spacious living room features exposed wooden beams above, with a cozy seating arrangement of soft sofas. A rustic wooden coffee table sits in the center, surrounded by warm, terracotta-tiled floors. A classic fireplace provides a focal point, complemented by thoughtful decorative accents.
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!
Guest favorite
The exterior of a charmingly rustic house is framed by olive trees, showcasing a stone facade and a gated entrance. Steps lead up to the entrance, surrounded by lush greenery and potted plants. A glimpse of a patio area is visible in the background.
Home in Scandicci
4.92 out of 5 average rating, 52 reviews

Le Piccole Scalette "Under the Tuscan Sun"

JoelRating, 5 stars1 month ago
We had a wonderful time. Truly felt like we were under the Tuscan sun. The views from all of our bedrooms were breathtaking. Patrizia was so lovely, so attentive, so thoughtful - made reservations for us at a few local restaurants, where of course, the food was amazing. Patrizia responded to our texts quickly and was so helpful across the board! The location is off the beaten path, but close to some smaller towns and only about 25 minutes into the heart of Florence. You will need a car to get to and from anywhere. It was easy enough to take day trips, driving to so many wonderful towns to visit for the day, parking at one of the parking lots in each town, enjoying the day and returning 'home' to relax.
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 80 reviews

The charming cottage in Tuscany with breathtaking views

JetRating, 5 stars4 days ago
What a magical, unforgettable place to stay! The home is the perfect size for two, and we felt right at home. It’s very clean with plenty of towels, blankets, pillows, and cooking appliances. We really enjoyed waking up to the sound of birds singing and having breakfast on the patio before making excursions to Siena, Florence, Poppi, or nearby Rufina. The neighbor’s cats also greeted us home when we returned (very lovingly!). Would absolutely love to stay again!
Guest favorite
A charming stone house from the 18th century is framed by vibrant greenery and flowering plants. The entrance is adorned with blooming roses, leading to a cozy patio area that provides a glimpse of the inviting atmosphere created by multiple plants and well-kept gardens.
Home in Vinci
4.95 out of 5 average rating, 21 reviews

Casa Marcello

QinRating, 5 stars2 weeks ago
Great experience, splendid house and still a very hom
Top guest favorite
A spacious living area is presented, featuring a contemporary sectional sofa adorned with cushions. The room is highlighted by a stone accent wall and a modern fireplace. Large windows provide natural light, while a round coffee table sits centrally, enhancing the inviting feel of the space.
Home in Monteroni d'Arbia
5 out of 5 average rating, 10 reviews

Golden View - Dream farmhouse in Tuscany

JamesRating, 5 stars4 days ago
Perfect peaceful location. In the countryside but close to amenities and 25 minutes to historic Siena with endless restaurants. And in secure gated area. Beautiful views and amenities in the apartment, with sauna and indoor and outdoor hot tubs. A must stay if looking for quiet, peaceful Tuscan experience.
Guest favorite
An outdoor terrace is shown with a dining table set for meals. Comfortable chairs surround the table, and vibrant plants add greenery. The expansive view of rolling hills under a clear blue sky is prominently featured, providing a serene backdrop.
Home in Montespertoli
4.94 out of 5 average rating, 88 reviews

Terrazza paradiso - For family and friends

AnkeRating, 5 stars3 weeks ago
This airbnb is in a stunning location and the house is absolutely beautiful- it is super clean and we were extremely comfortable; the terrace is lovely, very spacious and the interior is beautifully designed throughout. As for the location, there is a Coop nearby, roughly a 5 minute drive or a 10-15 minute walk. The village has a bakery and an optician, a little pizza take away place etc and some restaurants which we did not try as we were on day trips to either Pisa, San Gimignano, Florence (park and ride), Lucca, Siena, Arezzo, Livorno or Pistoia - all reachable within about an hour and each location had its own charm. I can recommend the house/location for its homely feel. It is definitely worth a visit! The few queries I had were replied to within a few minutes. Thank you for letting us stay.
Superhost
A living area features light pink walls and terracotta tile flooring. A spacious sofa and a wicker chair are arranged around a small table. Natural light filters through sheer curtains, illuminating the space. An arched doorway leads to another room, adding architectural interest.
Home in Montespertoli
4.82 out of 5 average rating, 49 reviews

Chiantihouse

PascaleRating, 5 stars8 months ago
warm welcome with great tips for sightseeing and restaurants. Fabio is very available and ready to help. Beautiful surroundings.

Private house rentals

Superhost
A tranquil swimming pool is surrounded by a well-maintained garden, reflecting the soft colors of the sunset. Lush greenery and vineyards are visible in the background, enhancing the serene atmosphere, while comfortable loungers are placed nearby for relaxation.
Home in Barberino Tavarnelle
4.8 out of 5 average rating, 54 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

RyanRating, 5 stars1 month ago
Beautiful home near Chianti. Clean and comfortable, with amazing vineyard/sunset views. The hosts were very responsive and friendly, and they gave clear instructions. One thing to note is that the property is listed as "Entire Home", but it is actually a condominium that shares walls and outdoor common areas with the neighbors. There is a divider in the backyard between us and the neighbors, but it is not completely private. Overall, we had a great time here.
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.97 out of 5 average rating, 32 reviews

Family Forest - Pool in the Crete Senesi

Majed Rating, 5 stars3 weeks ago
A beautiful and quiet place, surrounded by nature, scenery and host, friendly and available to answer all questions at any time , everything was great ..
Top guest favorite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
5 out of 5 average rating, 20 reviews

Villa le Scope 5*

ColeRating, 5 stars4 days ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Top guest favorite
A rustic farmhouse features a warm yellow facade with a terracotta roof. Shaded areas are provided by tall cypress trees. A charming entrance is highlighted by blue wooden shutters and a red door. Colorful flowers and greenery frame the home, contributing to the inviting outdoor setting.
Home in Barberino Tavarnelle
4.89 out of 5 average rating, 61 reviews

Farmhouse I CACHI - Chianti Tuscany, pool & ten

SamRating, 5 stars8 months ago
The only thing more amazing than the Farmhouse itself was the host. Let's start with the house - it is a second house on a larger property, yet still was more than big enough for our group of 5. It had a very rustic feel, which was just what we were looking for in Tuscany. The grounds include a pool and tennis court, both of which were in amazing condition and used by our group. The location was picturesque, and we relaxed on the grounds and enjoyed the amazing views. Now for the host - he was extremely responsive and kind. He went out of his way to ensure we had an enjoyable experience, including recommending local restaurants and wineries. Our rental car got a flat tire in the middle of Tuscany and he came to pick us up during the middle of the night, and helped coordinate a tow truck the following day. I could not recommend this Air BnB any more, and look forward to coming back in the future.
Guest favorite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 95 reviews

Casa Luigi Suite with exclusive pool

RachelRating, 5 stars2 weeks ago
Our stay at Casa Luigi with Giovanna and Luigi was absolutely perfect. I wish I could give it more than 5 stars. Not only was the place absolutely spotless, even the grounds were perfectly attended to and such a pleasure to walk through and sit in. Giovanna and Luigi were both so kind and friendly - we felt right at home. The apartment itself was very comfortable and had everything our family of 4 needed. My two teenage daughters were thrilled to have their own sleeping spaces and greatly enjoyed just staying at the apartment to enjoy the space and the grounds on a few days. It was the first place on our trip all over Italy where we actually wanted to stay at the Airbnb instead of sightseeing! I wish we could have stayed longer. This place is an absolute gem and I cannot express how much we absolutely loved our stay there!
Superhost
The stone mansion, reflecting rustic architecture, is set in a verdant landscape. A spacious lawn leads to the property, with elegant trees framing the view. The newly added exclusive pool is visible, inviting relaxation under the clear sky, just 15 km from Florence.
Home in San Casciano In Val di Pesa
4.95 out of 5 average rating, 42 reviews

[Villa San Jacopo Florence] Pool | Vineyards

MichaelRating, 5 stars3 weeks ago
We were a group of 10 staying Friday to Sunday at the villa. It is nestled in the beautiful Tuscan countryside. The rooms are spacious and the common areas perfect for a large group. It was very clean throughout. The kitchen is well designed and easy to use for a crowd. We deployed the large BBQ for a meal at home on the first evening. A cocktail, a steak and a view of the rolling hills - how charming! I would strongly recommend renting a car or cars because the village is some walk away. There is a large and well stocked Co-op about 10 minutes’ drive from the property. Giulia on behalf of the host was simply brilliant. She was very responsive and helpful, and full of good recommendations. I would not hesitate to endorse this property and its management - we had a brilliant stay and would happily come back again.
Top guest favorite
A gravel pathway meanders through a serene landscape, flanked by tall cypress trees. Lush greenery surrounds the area, with hints of olive trees visible in the background under a clear blue sky.
Home in Vinci
5 out of 5 average rating, 11 reviews

Il Palagio

MohammadRating, 5 stars1 week ago
Outstanding accommodation. Pristine, spacious yet very cozy. Very helpful host. 10/10 would come again
Guest favorite
An expansive infinity pool is surrounded by lush greenery, reflecting the clear blue sky. Sun loungers are positioned along the pool’s edge, inviting relaxation. The gentle slopes of the Chianti countryside provide a serene backdrop, enhancing the tranquil outdoor setting.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 67 reviews

Chianti House Stunning view 20 min. from Florence

AshlynnRating, 5 stars7 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!

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