
House holiday rentals in Grassina
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Top-rated house rentals in Grassina
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House rentals with a pool

dependance in villa Toscana
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

Borgo Bottaia "L'Arrampicata" 5 pax
An absolutely beautiful Borgo in the Tuscan Hills with easy access to Florence by car or bus. Better in real life than in the photos! We loved our time staying at Borgo Bottaia and would stay there again.

Private villa/swimming pool in Tuscany
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!

Charming estate with views
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

The Owl: view, pool and garden
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.

Casa di Lyndall - Entire house with exclusive pool
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Antico Borgo Ripostena – n. 8 Old House
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

Country House w/ heated Pool near the City Centre
Giacomo greeted us right away once we areived to his beautiful home. Him and his wife navigated us throughout the home and described how to use all the amenities. He was kind and always available when we needed something. The home is beautiful, private and is surrounded by gorgeous nature. I highly recommend Giacomo's home. Thank you for everything!
Weekly house rentals

Casa del Gelsomosino
The house is very cozy and spacious. The well-equipped kitchen, the bedroom with very comfortable mattress and pillows, the very spacious and above all extremely clean bathroom, as in general the whole house, very clean and fragrant. The house also remains very cool, despite the high temperatures we found during our stay. It is located in the hills a stone's throw from Florence, in a super quiet village surrounded by olive trees. Irene was always kind and very helpful, even giving us advice on a mechanic in the area as we had problems with our car. One small note: unfortunately, you can hear the "noises" coming from upstairs... those who are not early risers could be woken up.

New Florence “David” apartaments with private pool
Wonderful, had a lovely time and it was all as we imagined, Simone is extremely accommodating and has a helpful answer to any question. Top Air bnb

Podere Tignano, 4-bedroom villa in the Chianti!
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!

THE RED BARN - private garden and swimming pool
Some places don’t feel like destinations — they feel like memory. Even if you’ve never been there before. The Red Barn in Impurneta is that kind of place. It’s hard to explain without slipping into clichés, but the truth is… it felt like coming home to somewhere I didn’t know I’d left. A patch of land so beautiful, so utterly peaceful, that it silences the noise in your head you didn’t realize was there. The views stretch forever, soft and golden, like the world finally exhaled. The air is kind. The silence is full. You don’t just stay here — you heal here. Every inch of the property felt intentional. Familiar. Like a childhood memory you thought you’d imagined, but turns out was real all along. I can’t explain it. And maybe I shouldn’t try too hard. Some places just are. And this place — it’s special. We left slower than we arrived. Not because of the luggage or logistics, but because a part of us wanted to stay. Maybe always will. And if we’re lucky, life brings us back here aga

The charming cottage in Tuscany with breathtaking views
So Beautyful location and views. House is charming and clean. we recommend.

"La Cappella" ancient country church
La Capella was beautiful! Titti was there to welcome us and made sure we had everything we needed. This stay is in between the beautiful Tuscany country and the city of Florence. Perfect to get both experiences! We would absolutely stay here again!

Residenza Carlotta - Luxury and design beside Arno
Fantastic airbnb in the heart of Florence! Walkable distance to all main attractions- incredibly beautiful restored apartment which felt more like a house as it is on two floors. Without a doubt the best airbnb i have ever staid at

Chiantishire Cottage
We had a wonderful stay at Chiantishire Cottage. A very beautiful house with an even more beautiful view close to Florence. Highly recommended for anyone who likes peace and quiet, but close enough that you can easily visit a town by car. The daily visits of the sweetest dog Camillo made our vacation even more memorable. I would recommend Chiantishire Cottage to everyone.
Private house rentals

7 min Cantina Antinori | Pool | Casa Sala & Pepe
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.

Bright barn in the hills just beyond Florence
Exceptional in everyway. One of the most beautiful homes I have ever stayed. Additionally, Antella is a lovely town and only a short distance from Firenze. It is the best of all worlds, living in the countryside only a short distance from one of the most beautiful cities in the world. I must also add that Bianca and Andreas are two of the nicest people you will ever meet. An incredible place.

[Little Escape] 4 Beds + Private Panoramic Pool
Our stay in Montebenichi was almost indescribable. Having been to Tuscany before, this time was pure magic. The flat is within the compound of a 12th century fortress village that is mostly inhabited by residents. Tommaso had stocked the kitchen with plenty of coffee, milk, water, juices, snacks and his grandmother's amazing Limoncello! The pool area has the most incredible view with an outdoor kitchen where Tommaso arranged for us to have a traditional Tuscan cooking class. He also made reservations for us at the village Michelin-rated restaurant that is just steps from the flat. One of our favorite things was hearing the wolves of Tuscany howl in the distance - no need to be afraid - it was pure magic. We saw very few tourists which made the experience even better. Moreover, Tommaso was THE BEST HOST we have ever had while staying at an Airbnb. His dedication to ensuring the perfect stay for us was truly a standout. We can not say enough good things about our stay!

Apartment in Villa - Private Parking and Terrace
Our extended family had a wonderful Christmas in Francesca‘s lovely home. We enjoyed the art and the cozy comforts. The kitchen is well equipped to cook and serve a beautiful holiday meal. We hope to be back!

Sassineri Country House
Unique accommodation with all the comforts. The pool and barbecue area are worth the stay.

La Loggia – Casine al Sole
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.

Sweet life in Tuscany , but so close to Florance
We had a lovely stay and Simona was keen to ensure that we were happy. The villa has a lovely rustic feel. Ignore the no entry sign at the end of the dirt track road and drive up through the trees. You park right outside the house. It was a little more expensive for us as we were only 2, staying in a place for 4. The dog was lovely and friendly ( although looks as though he might not be as Alsatian breed I think ). There is a lovely restaurant in San Polo with a lovely garden out the back… about 7 mins away.

Supersuites with breathtaking views in Chianti
I could not wait to write this review! AMAZING place to stay. We stayed at Silvia’s house for 2 nights with our 3 children, I wish we could have stayed longer. From the moment we arrived we were greeted with warmth, respect and kindness. In fact, Kindness radiates from Silvia and her husband, both of them could not of been more lovely, their hospitality was charming and humbling. The home was traditional, yet cosy and comfortable the views are spectacular and our children of course were very happy in the amazing pool! We took a day trip to Florence which was 20 min drive, you can also reach by bus. If you choose to stay here you will feel like part of the family, Silvia had lots of lovely little gestures that go above and beyond, and Michael was always there for recommendations and to answer any questions. He even booked us a reservation at a local restaurant for the night we arrived, fabulous meal and place! We won’t forget this place. And we certainly won’t forget the hosts.
Quick stats about house rentals in Grassina
Total rentals
20 properties
Nightly prices starting at
₹5,182 before taxes and fees
Total number of reviews
960 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- Palazzo Vecchio
- The Boboli Gardens
- Spiaggia Marina di Cecina
- Santa Maria della Scala
- Nelson Mandela Forum