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House vacation rentals in Castelfiorentino

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Popular amenities for Castelfiorentino house rentals

House rentals with a pool

Guest favorite
A serene outdoor area features a swimming pool surrounded by lush greenery and olive trees. Sun loungers are positioned on the wooden deck beside the pool, while a covered seating area provides shade. Scenic hills and a distant villa are visible in the background.
Home in Pistoia
4.92 out of 5 average rating, 133 reviews

dependance in villa Toscana

DustinRating, 5 stars2 weeks ago
My wife and I stayed at Marco’s for a week for our honeymoon. We both loved it. Pool was beautiful and peaceful. The property is fantastic the pictures don’t do it justice. As amazing as it looks in the photos it is 1000 times better in person. The front gate made everything feel so secure. Walking up the steps to the guest house we were hit with a nice floral smell with all the daisies growing everywhere. Such a peaceful and beautiful property. The view was stunning looking over the mountains. The place was perfect. The kitchen was everything we needed and more, the pull out couch allowed us to relax and watch tv at the end of the night. The patios were perfect for coffees and meals. And the bed was nice and comfortable. Marco left a flower pedal heart on the bed for us which was a nice personal touch. We met his parents (who stay in the main house) they were very kind and gave us our privacy. There was lots of information about the area and things to do. Wish we stayed longer
Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.
Guest favorite
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 93 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars2 months 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
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, 140 reviews

Casetta Melograno – Cozy farmhouse in Chianti

JacobRating, 5 stars1 week 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.
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, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars1 month ago
What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.
Superhost
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 stars1 month 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
A charming stone barn features a wide entrance with wooden pillars, framed by vibrant yellow flowers in the foreground. Steps lead to the door, surrounded by lush greenery and a serene landscape, highlighting the peaceful atmosphere of the Tuscan countryside.
Home in San Gimignano
4.98 out of 5 average rating, 46 reviews

La Moraiola - Characteristic Tuscan barn

LinasRating, 5 stars2 days ago
Egizia’s home was the ideal place for our family’s Tuscan getaway. It had everything we needed. Egizia was an excellent host, great communicator, great recommendations. We would stay here again.
Guest favorite
A rectangular swimming pool is situated in front of a rustic stone farmhouse. Five lounge chairs are arranged along the pool's edge, with an umbrella providing shade. The building features green shutters and is surrounded by lush landscaping.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 69 reviews

Chianti House Stunning view 20 min. from Florence

ThompsonRating, 5 stars4 days ago
Tommaso was very responsive and fantastic! Check in was a breeze. The pool was great. Overall, it was a great stay for our trip in Tuscany!

Weekly house rentals

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
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks 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!
Superhost
A sunlit garden area features a reclining lounge chair positioned on lush green grass, surrounded by rolling hills and trees. The scenery offers a clear view of the countryside, with a bright blue sky and fluffy clouds enhancing the serene atmosphere.
Home in Gambassi Terme
4.85 out of 5 average rating, 27 reviews

Finest country house. 3 bed rooms and shared pool

HelenRating, 5 stars10 months ago
Enjoyable stay. Close to many beautiful towns.
Guest favorite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 99 reviews

Explore Chianti from a Charming Stone House

ShelbyRating, 5 stars1 week ago
Best part of our Italy trip! We loved our stay at Casa Marinella, and Monica has thought of every detail to make for a wonderful and peaceful vacation! Relax by the pool and enjoy breathtaking views. Be sure to stop by Gelateria di Castellina for a scoop of cremino gelato and try the fiorentina steak at Osteria La Sosta di Pio VII.
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 83 reviews

The charming cottage in Tuscany with breathtaking views

PoojaRating, 5 stars2 days ago
Stella is a beautiful person and a perfect host. Everything immediately felt like home. She explained everything very nicely. The location was serene and she gave a lot of information on things to do in that area. Would love to come again for sure.
Guest favorite
A bright kitchen features a large wooden window overlooking a leafy garden. Fresh flowers are arranged in a vase on the countertop, accompanied by a bowl of eggs. Natural light enhances the space, highlighting the white cabinetry and sink area.
Home in Colle di Val d'Elsa
4.94 out of 5 average rating, 65 reviews

Countryhometuscany - House with Garden -

GabrielleRating, 5 stars2 weeks 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.
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, 97 reviews

Casa Luigi Suite with exclusive pool

DerekRating, 5 stars3 days ago
I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.
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 stars1 month 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 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, 14 reviews

Golden View - Dream farmhouse in Tuscany

KshitijaRating, 5 stars6 days ago
This has to be one of the nicest Airbnbs we’ve stayed it. The accommodation was luxurious in an absolutely stunning area of Tuscany. The rolling fields and cypress tree made a spectacular setting for this beautiful house. We had hired a car and this place was a 20 minute drive from Siena. Our only regret was not staying here longer.

Private house rentals

Guest favorite
A stone house with a rustic charm is enveloped by lush greenery and blooming wisteria. Large windows and a distinctive arched window enhance the facade, while vibrant plants add warmth to the exterior. The surrounding landscape features rolling hills in the distance under a partly cloudy sky.
Home in Fiesole
4.97 out of 5 average rating, 32 reviews

Scenic country house with large pool near Florence

ChristopherRating, 5 stars1 month ago
Absolute Perfection in Fiesole!** Michael’s villa in Fiesole is nothing short of spectacular. From the moment we arrived, we were mesmerized by the breathtaking views of the Tuscan countryside and Florence in the distance. The location is ideal—peaceful, romantic, and just a short drive from the heart of Florence, making it the perfect blend of serenity and convenience. The villa itself is stunning—spacious, elegantly decorated, and equipped with every amenity you could need. The outdoor terrace was our favorite spot, where we enjoyed morning coffee with panoramic views and evening wine under the stars. The lush gardens and private pool added an extra touch of luxury to our stay. Michael was an exceptional host—attentive, welcoming, and full of great local recommendations. His hospitality truly made our experience unforgettable. If you’re looking for a dreamy Tuscan escape with world-class scenery, impeccable style, and top-notch service, this is the place. We can’t wait to
Top guest favorite
A bright sitting area features floral-patterned sofas arranged around a wooden coffee table. A decorative fireplace is centered against the wall, accompanied by built-in shelves displaying various items. Natural light enters through large windows, enhancing the soft color palette of the room.
Home in Lucca
5 out of 5 average rating, 15 reviews

Elegant ancient villa Lucca

LeahRating, 5 stars1 month ago
From the moment we were greeted by Isabella, Massimo and their son, to the moment we said goodbye we felt right at home. The house is well located. It was nice to leave the hustle of the old city and retreat to the expansive peaceful terrace of the house for an “aperitivo” before dinner. The beds were comfortable and we all slept well after long days of touring. One of our favorite things was collecting water from the town spring, which was just a few doors away.
Top guest favorite
An outdoor seating area features four wooden chairs arranged around a central table. The view highlights rolling hills and lush greenery, with mountains visible in the distance under a clear blue sky.
Home in Montecatini Alto
5 out of 5 average rating, 33 reviews

Montecatini Alto Art View

GarethRating, 5 stars6 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.
Guest favorite
An outdoor pool is set within a wooden deck, surrounded by greenery and overlooking the hills of Tuscany. Sun loungers are positioned nearby, with an umbrella providing shade. The clear water reflects the open sky, enhancing the serene landscape.
Home in Certaldo
4.94 out of 5 average rating, 33 reviews

Tognazzi Casa Vacanze - Panoramic Villa

CarlieRating, 5 stars3 weeks ago
Wonderful home for our family of four including a one year old and three year old. Authentic, private, clean and in an amazing location with a beautiful view. This was our favourite Airbnb of all time.
Top guest favorite
An aerial view depicts the medieval village of Palaia, characterized by its charming terracotta rooftops and lush greenery. The surrounding Tuscan hills create a scenic backdrop, with a glimpse of the communal garden featuring a swimming pool. The landscape reflects the authenticity of the area.
Home in Palaia
4.98 out of 5 average rating, 45 reviews

Conte Martini House

BoydRating, 5 stars3 days ago
Andrea en Simone, Are very welcoming, the location is a smal walk but with good directions easy to find. Palaia and the accommodation has amazed us, with a amazing home away from home. Great facilities, terrace, jacuzzi, pool, and not to forget amazing views. As a base to explore there is alot of interesting places to go to witin a hour drive. big cities, smaller towns, wineries, and with a tiny bit extra travelling time the sea. We had a great stay with our friends and made some great memories. would recommend the accommodation, as well as the hosts, and would definitely stay again. Kind Regards, Boyd and Naomi
Top guest favorite
A private pool is surrounded by lush greenery and flowering shrubs, inviting relaxation. Lounge chairs are positioned nearby under the shade of trees, creating a serene outdoor space. The pool area is accessible, providing a peaceful retreat for guests.
Home in San Gimignano
4.98 out of 5 average rating, 41 reviews

Tuscany:Stone house, private pool and garden

MarceloRating, 5 stars1 week ago
This house is the perfect place for two families traveling together. It’s incredibly cozy, thoughtfully designed, and fully equipped with amenities that let you truly enjoy the beauty of the Tuscan countryside. From the moment we arrived, we felt at home. The hosts went above and beyond — welcoming us with fresh fruit, traditional sweets, bottled water, coffee, milk, and a selection of Tuscan wines, which we truly appreciated. They also provided high-quality Italian hygiene products, which added a thoughtful and luxurious touch to our stay. One of the highlights for us was the host’s responsiveness. Communication was always fast, helpful, and friendly — a detail that made a big difference. We didn’t get a chance to use the private pool due to our tight schedule, but the property still gave us a real sense of independence, comfort, and safety. I 100% recommend this property. It’s a peaceful, beautiful place — perfect for relaxing, connecting with nature, and creating memories
Top guest favorite
The image captures a scenic view of a rustic home surrounded by lush olive groves and rolling hills. The two-story structure features a traditional tiled roof and green trees providing shade. The open landscape beyond displays a peaceful natural setting, evoking a sense of tranquility.
Home in Vinci
5 out of 5 average rating, 81 reviews

Villa Vestra in Vinci holiday home

Laura And ArnRating, 5 stars1 day ago
My husband and I had the great pleasure of spending 8 days at this beautiful Airbnb. Truly, this is the best Airbnb we've ever stayed in, and we travel a lot! With big intentions to explore the Tuscan area we essentially did nothing and stayed put. Why? It's just that beautiful. The view is spectacular, and the accommodations are very comfortable. The hosts have provided everything you need for a deep relaxing holiday. Of course if you choose to explore, there is much to see and do in the local area. We'll save all of our exploring for next time! Thank you Sylvia and Julio for a magic vacation.
Guest favorite
A traditional stone house with a sloped roof features wooden shutters and a central door. An awning provides shade over a dining table set on a well-maintained lawn. Surrounding flowers and greenery create a peaceful outdoor setting, reflecting a serene countryside ambiance.
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.

Destinations to explore