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House vacation rentals in Valpiana

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Popular amenities for Valpiana house rentals

House rentals with a pool

Guest favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars2 days ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
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!
Guest favorite
An outdoor swimming pool is surrounded by green grass and features a clear blue water surface. Sun loungers are positioned nearby, while a panoramic view of hills and distant landscape can be seen in the background. The area is well-lit and inviting.
Home in Catabbio
4.89 out of 5 average rating, 159 reviews

Country house La Meria

AlexRating, 5 stars1 month ago
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!
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
Guest favorite
A serene stone pool reflects the clear sky, set against a backdrop of lush trees and rolling hills. The inviting water is framed by a stone deck, with a single umbrella providing shade nearby. The tranquil landscape offers a peaceful escape.
Home in Pievescola
4.94 out of 5 average rating, 173 reviews

Antico Borgo Ripostena – n. 8 Old House

HannahRating, 5 stars3 weeks ago
Beautifully finished holiday home in a lovely peaceful setting with great views. Well set up for small children, with toys and play area in the communal spots and a toy box in the apartment on request. Martina was an excellent host, very responsive and helpful. Thank you!
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!
Top guest favorite
Aerial view of a rustic stone house surrounded by greenery and olive trees. A rectangular pool is visible, with turquoise water and purple umbrellas shading lounge chairs. The expansive garden features lush grass and landscaped foliage, providing a serene and spacious outdoor environment.
Home in Volterra
4.93 out of 5 average rating, 179 reviews

Collina Power

DeanRating, 5 stars1 week 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
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!

Weekly house rentals

Top guest favorite
A private garden is surrounded by greenery, featuring a wooden deck with a dining table and chairs. A lounge chair rests on the grass, complemented by colorful flowers. Stone walls of the house provide a rustic backdrop, enhancing the serene atmosphere.
Home in Suvereto
4.96 out of 5 average rating, 47 reviews

The house in the Castle and the secret garden

SallyRating, 5 stars2 weeks ago
What an incredible place to stay! Diana opens up her whole home to you and it is so welcoming, plus has everything you need for a relaxing stay. The architecture of the building itself is beautiful and Diana has lovingly restored this, the interiors are well thought out and the space is used cleverly to make use of the space in the apartment. The house guide has really great information about the area, and Diana was kind enough to offer us more tips on things to do, plus booked some reservations for us for dinner. Thank you for being such an attentive host, it made our stay much more enjoyable.
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 vibrant yellow house stands amidst greenery, featuring multiple windows with dark shutters. A hammock is stretched between two trees, offering a relaxing spot. In the foreground, a dining set with chairs is visible, providing an outdoor seating area surrounded by grass.
Home in Bivio di Ravi
4.96 out of 5 average rating, 49 reviews

Casa Elicriso

BettyRating, 5 stars3 days ago
We only stayed a night as we had extended our trip by a day but I would’ve stayed longer! The hosts were very nice and accommodating, they were responsive and gave us local tips on beaches etc! The place was just as they described. The area was peaceful and the garden was cute during the day and night! I would definitely recommend :) thanks so much!
Top guest favorite
A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.
Home in Montemassi
4.96 out of 5 average rating, 48 reviews

Capezzuolo 33

MathildeRating, 5 stars3 days ago
Amazing. We fell in love with Tuscany and with Montemassi. Lucia and Marco’s place is a little cozy nest in the most beautiful surroundings. If you like wine, you’ll be happy with all the beautiful wineries nearby. Would definitely come back! Thanks to Lucia and Marco for the amazing welcome and for their attention to detail!
Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 79 reviews

Captain's House | Monte Grosso, Elba

CaterinaRating, 5 stars1 week ago
The Captain's House is a place that reconciles you with the world. Beauty is experienced for the eyes, spirit, and mind. The views are breathtaking, the view from every window is a painting, and peace and tranquility are guaranteed. The hosts have created a masterpiece by renovating the house: they have respected the original structure by adding every possible comfort. Andrea and Michael are very kind, they anticipated all our possible needs, they provided us with fresh flowers and fragrant herbs in every room, fresh fruit and everything necessary to "start" the kitchen (oil, salt, spices, etc.). Due to a technical issue, we were unable to use the Jacuzzi for one day and they offered us a dinner to apologize. We've never found hosts of this level. We hope to be able to go back and take back those pieces of our hearts that we left at the Captain's House.
Top guest favorite
A bright interior space is shown, featuring a table with chairs set for breakfast. A cozy sofa is positioned nearby, and a cabinet holds decorative elements. A well-equipped kitchenette is visible, with dishes neatly arranged on the counter. A window offers a view of the outside garden.
Home in Roccastrada
5 out of 5 average rating, 5 reviews

Apartment in the countryside

Dr. SveaRating, 5 stars9 months ago
Exceptionally beautiful apartment furnished with a lot of love and taste in a beautiful, well-kept complex! The beautiful, well-kept pool is the icing on the cake that makes the complex perfect. We really enjoyed the four-course dinner under the stars, but there are also so many good restaurants in the area that you can't try them all. Chiara and Stefano are the perfect hosts, you can learn a lot of interesting things from them! They also attach great importance to sustainability, the facility is self-sufficient and only organic wines are produced in the associated winery.
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
A logo featuring a house with a welcoming doorway, adorned with potted plants on either side. The design includes the text 'DEPENDANCE LA BANDITA' and 'ESTD 2023,' framed by delicate floral elements, suggesting a curated and inviting space.
Home in Marina di Castagneto Carducci
4.98 out of 5 average rating, 55 reviews

La Bandita Dependance

JonasRating, 5 stars1 week ago
Azzurra's place was one of the best, if not the very best, AirBnB we have ever stayed at. The flat is great and the grounds are absolutely stunning. Best of all, though, it is located within a short drive of some of the most stunning spots in Italy, with plenty of variety for those that want it (beach, vineyards, old towns, etc.) On top of all this, Azzurra was super responsive and attended to our every need. We would stay here again in a heartbeat. A small highlight are Oliver and Duccio, their two dogs, who often joined us for breakfast and lunch in the garden.

Private house rentals

Top guest favorite
A panoramic view depicts rolling green hills extending toward the coastline. The azure sky is adorned with scattered clouds, while the sea glistens in the distance. A sheer curtain is visible in the foreground, framing the serene landscape.
Home in Campiglia Marittima
5 out of 5 average rating, 37 reviews

apartment in farmhouse

ChantalRating, 5 stars1 month ago
Gorgeous place, warm and generous host - this is a unique experience where everything feels good, with eye for detail and comfort. Nice daytrips (Petra Winery and villages, coast) to be mixed with relaxing and enjoying the view. Very grateful for the three days, the kindness, dog Pepe, the fab handpicked wild flower bouquets and nice conversations. Going up and down the mountain is an experience too and so worth it!!!! Big thank you Susanna, also for the drives and the car! Would love to come back & we recommend this big and comfi appartement for 2-3 day stay or longer!
Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars1 week ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favorite
An outdoor terrace features a table and chairs surrounded by lush greenery and potted plants. A bar counter with stools offers scenic views of the expansive Tuscan landscape, with rolling hills and a clear blue sky visible in the background.
Home in Monterotondo Marittimo
5 out of 5 average rating, 25 reviews

Villa Tuscany 5 bedrooms panoramic terrace

SannaRating, 5 stars5 days ago
We had a fantastic stay at Giada’s house! The house is just as beautiful as it looks in the pictures, but the view is something you simply can’t capture in a photo – it’s breathtaking. The house was the perfect size for me and my three friends, and it had everything we needed to relax and enjoy a peaceful holiday. The village has a small shop and a couple of restaurants, which suited us perfectly. I hope to return to the house and the village someday in the future! Giada is very friendly, helpful, and quick to respond to messages. She deserves a warm thank you for her patience – our flight was heavily delayed and we didn’t arrive until after midnight, but it was no problem for her, and she responded even at that late hour. The house is a perfect place to stay for those who want privacy, to spend lots of time outdoors, and just unwind. Simply a perfect accommodation. Looking forward to our next visit!
Guest favorite
An outdoor dining area is showcased under a shaded pergola, featuring a large table adorned with a colorful tablecloth. Surrounding the table are white chairs with a scenic view of vineyards, and a stone barbecue area is positioned nearby.
Home in Suvereto
4.86 out of 5 average rating, 14 reviews

Art Beds & Garden

SalouaRating, 5 stars7 months ago
This apartment is absolutely exceptional! Everything is perfectly combined for a memorable stay in this beautiful area: strategic location, close to the thermal baths, superb beaches!!! just 1.5 hours from Siena, Florence, and close to Pisa. The exteriors are pleasant, and everything is designed to make everyone feel comfortable, and even more. We were a group of 9 (adults, teenagers, children and a baby), and we all found our space thanks to an optimal layout. The apartment is huge and nicely decorated. As for Monica, she is much more than welcoming, she is a real gem! Her kindness, hospitality, clarity, understanding and adaptability far exceeded all our expectations. She made us feel perfectly fine. I highly recommend this unforgettable experience in this wonderful area. Thanks Monica!
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!
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
Home in Pereta
5 out of 5 average rating, 54 reviews

Bel Casale with sea view and the mediaeval village

JustinRating, 5 stars1 week ago
I’ve been to many places but this is the first time I can say I was truly in love with a home. The pictures you see in the description are just a fraction of the beauty. The hosts are absolutely wonderful, the property is stunning, and it puts you in the heart of Tuscany. We will be back time and time again.
Guest favorite
The exterior of a rustic stone building is captured, featuring terracotta pots with young citrus trees planted in front. A gravel driveway leads to the entrance, with steps ascending to the porch. A red tractor is positioned to the left, enhancing the agricultural setting.
Home in Gerfalco
4.94 out of 5 average rating, 48 reviews

Barn of Vignanova in Alta Maremma (Montieri)

PhilippRating, 5 stars3 weeks ago
A wonderful quiet stay. If we had known how the street to the place of residence was, we probably wouldn't have booked it. Now, once we have made this trip, we would do it again and again. A wonderful place. Thx

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Valpiana
  6. House rentals