
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
Michael greeted us on arrival and was extremely welcoming and took time to show us around his beautiful home. This was a family holiday with 6 adults and the ample space both inside and out worked perfectly for us all, we felt at home and relaxed. The whole house is extremely luxuriously and well equipped, we used the BBQ and the pizza oven both of which worked perfectly. Michael was always available to help with any questions we had and the location is perfect for day trips to Firenze, Siena etc. We enjoyed a wonderful week and would thoroughly recommend Michael’s home.

New Florence "Afrodite" suite with pool
Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!

House with pool among olive trees plantation
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.
We were very pleasantly surprised! Perfect for a peaceful stay with a group. I absolutely recommend:)

Country Cottage with Pool "Il Melograno"
Charming villa in total relaxation. Lots of green space and a beautiful pool... all just for us. Giovanni was super welcoming and kind. An experience to repeat, highly recommended! Greetings from Fede and Kevin

Countryside house with private pool and garden
Such an amazing place! I would recommend EVERYONE to go there! Violante and her husband are such nice hosts. We had a wonderful time there and will not hesitate to come back next year. Thanks a lot.

Paluffo Tower House
We had such a fantastic stay (family of six). Only disappointment was having to leave. The setting and hospitality was great. The stairs within the tower unit proved a little onerous but only added to the historic feel… plus the view once on top made the climb more than worth it. Also, the cooking class with Monica was terrific. She was excellent and very patient and playful with our children. We hope to return again soon.

Nada Home
Comfortable house in the Tuscan countryside. Beautiful views, and easy to manage day trips to surrounding areas. Nada was great at communicating and had many recommendations. Her daughter coming for a cooking class was a fun afternoon activity.
Condo rentals with a pool

Adalberto Apartment inside the Manor of Fulignano
Great stay, incredible views, good location….

Casa Rebecca with a small private pool
Perfect accommodation to find peace and quiet, we were unable to use the pool due to the temperatures but it is certainly a great comfort for the hottest days! Benedetta was a very hospitable and kind host (as well as her beautiful dogs!). Highly recommended for relaxing and enjoying peace in the midst of nature.

Apartment Melissa
We stayed in the Melissa apartment and it was great, very spacious and bigger than expected. The apartment is self-catering and has all that you need to cook and have a great time. There is no terrace for this apartment, but they are many areas around the property that allow for some outdoor time. The location was beautiful, amazing views, great swimming pool and an overall very relaxed place. The property is 15 mins away from San Gimignano and very close to the bigger towns/villages to visit. Having a car is a must. The staff, the welcome and overall communication was lovely and easy, I would definitely recommend staying here.

Three-room apartment with 2 bedrooms and private garden, swimming pool
Wonderful place, very nice host. Thank you for your hospitality, Silvia

The house in Chianti - IlVillinoFarmhouse
We loved our stay here. It took us a couple of attempts to find it - but we were driving in pouring rain and fog (which was actually very picturesque!). Liza’s instructions were very clear and she was patient and helpful with me as I navigated our way there. The space was lovely - my daughter slept on the pull out sofa bed and the configuration of the living room meant that it became a separate bedroom for her which she loved. Nearby Castellina in Chianti is an absolute delight of a town - just a few minutes away - and another 30 or so minutes further and you have all the jewels of the Tuscan region within easy reach. Thanks so much Liza and Daniela for looking after us. Bec and Maxine

Luxury Views aircon Shared Pool parking cooking
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!

lovely farm- apartment (Fox)
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.

Poggiolieto Studio - on hills 10' from city center
Very loving and sweet hosts. A very cozy and pretty accommodation. We liked it very much 🥰
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
The Stone House was gorgeous - beautifully and thoughtfully decorated, with amazing views. It was private yet easy to get to many amenities/tuscany towns/wineries nearby. Emanuela and Giovanni were very responsive to our questions and requests. We requested for help to buy a bouquet of flowers to surprise our friend for her birthday on the day we arrive - not only did they take the time to help us buy it, they refused to let us pay for it! it was too cold for us to use the pool but I can imagine how wonderful it would have been if we could have used it. all in all, it was a great place to enjoy a dreamy tuscan holiday.

The Nest by Interhome
"The Nest" in the Localitá Torri is a beautiful place. High-quality, absolutely complete and lovingly furnished. Penibel clean. There was nothing missing at all. There is a lot of passion in the apartment. This fits the owner who did the check in and check out himself. Such a pleasant, nice person. An ideal starting point for excursions to the well-known area with San Gimignano, Volterra, Siena, Florence, etc. Absolutely recommended

Il Poggio Farmhouse by Interhome
We had a very good time here! The Airbnb is a separate part of a nice house on a hill, it is spacious and has everything you need. You can sit outside and there is a nice swimming pool. The hosts were very nice and always available for help/tips. I definitely recommend this place!

Historic home with exclusive pool
We (7 friends) enjoyed staying at the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She sent us a lot of tips about the area (including the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed something, an answer came very quickly. The villa is well equipped and the surroundings are beautiful. There is plenty of parking space. Only the potholes and the access to the villa are a bit challenging - but doable!

Charming villa in the Chianti hills
We spent a few nice autumn days at Francesca's. It is much nicer than shown in the photos. The house is fantastically and quietly located on a hill. The amenities are high quality and Francesca was always available at short notice. We would definitely vacation there again.

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!!

Casa Luigi Suite with exclusive pool
Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!

The Barn by Interhome
We where met by the owners , talked through the villa, got directions to and from our venue As we arrived late we needed to eat, they found us a local restaurant and booked our table. They gave us two other restaurant recommendations, both of which we used , one of them twice. Incredible value for great fresh food, pizza and pasta.
Quick stats about vacation rentals with a pool in Grassina
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ294 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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- Duomo di Firenze
- Ponte Vecchio
- Teatro Verdi
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Basilica of Santa Maria Novella
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Mercato Centrale
- Stadio Artemio Franchi
- Pitti Palace
- Santa Maria della Scala
- Basilica di Santa Croce
- The Boboli Gardens
- Pinocchio Park
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Vecchio
- Teatro Tuscanyhall
- Piazza della Repubblica
- Teatro della Pergola
- Podere La Marronaia, Sosta alle Colonne
- Palazzo Medici Riccardi