
Vacation rentals with a pool in Grassina
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Top-rated rentals with a pool in Grassina
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House rentals with a pool

Scenic country house with large pool near Florence
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

Wonderful country house
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.

Cercis - La Palmierina
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

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!

Old barn The Nepitella
We had a very nice stay. We recommend this place.

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.

Paluffo Tower House
Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

Gaiole in Chianti Poggio Casabianca
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!
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

Adalberto Apartment inside the Manor of Fulignano
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

Casa Rebecca with a small private pool
Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

House between Firenze, Arezzo, chianti e Siena
We immediately fell in love with this property. Everything here makes up the image that can be made of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!

Ginestra: Private Pool Overlooking Florence
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.

New, bright, cozy Florence apartment with view
Super cozy and well-furnished apartment — clean, spacious, and quiet. Separate air conditioners in the living room and bedroom, reliable Wi-Fi, and a lovely balcony with a nice view. The location is peaceful and pleasant, just a few stops from the city center, with good grocery stores and restaurants nearby. I really enjoyed my stay here and hope to come back again in the future!

Belvedere
Marcello’s place felt serene and relaxing and our time here was just delightful. We absolutely loved the lemon garden we had all to ourselves, the grounds of the property are picturesque with a joyful companion of Tommy, Alina and Pistacchio. All is beautifully maintained and the apartment is elegant and cosy. We did appreciate proper mosquito nets, stable and fast internet for working, a proper dedicated workspace, sparkling clean apartment, great kitchen equipment, a garden table with a parasol offering plenty of shade, sun loungers by the swimming pool and a that the pool was kept very clean for us to be able to refresh in it during the hot days. Marcello is so friendly, warm and communicative. He spoilt us with his kind generosity and hospitality that you understand immediately why he is a super host, he really cares about his guests. Thank you so much dear Marcello for making our stay so enjoyable. We hope to be back one day.
Home rentals with a private pool

Sole by Interhome
Incredible host. Incredible house. You feel like you are inside a postcard. The most beautiful views are all around you. We did not want to leave. Just breathtaking.

Ambrogetta by Interhome.
Our stay unfortunately ends tomorrow and it was beyond our expectations🙏🏻 The Villa was exceptional, clean, cozy with spectacular views of the Chianti Plains❤️ The Villa, the pool, the flowers, the plants, the nature that surrounded us, allowed us to enjoy our vacation far beyond everything we could have imagined! Our host ,Signore Boncorso , made our stay unforgettable thanks to his exceptional hospitality and valuable advice! Grazie mille! A perfect score! 5 stars xxxxx A 5 Stars ⭐️⭐️⭐️⭐️⭐️ and more!

Stone House with Exclusive Pool Codilungo in Chianti
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Nicoletta by Interhome
Nicoletta greeted us at check in and gave us a tour of the property. She was always responsive and timely. The listing quite frankly undersold the size, space, and beauty of the entire package. The house kept its historical charm while offering the modern amenities including large updated bathrooms, pool, gardens, lounging areas, and a full kitchen. Staying here was truly and escape to the country side where the private pool overlooked an amazing and secluded view of the area. This house is ideal for those seeking an authentic Italian villa. It was really an amazing experience.

Explore nature in the center of Vigneti Chianti
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

Historic home with exclusive pool
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. There is plenty of parking. Only the potholes and the access to the villa are a bit challenging - but doable!

Charming villa in the Chianti hills
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.

Villa il Palagio in the Tuscan countryside
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Quick stats about vacation rentals with a pool in Grassina
Total rentals
50 properties
Nightly prices starting at
G$16,728 GYD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Ponte Vecchio
- 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
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Pinocchio Park
- Teatro Verdi
- Nelson Mandela Forum
- Palazzo Vecchio