
Holiday 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

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!

Sassineri Country House
Alloggio unico e dotato di tutte le comodità. Area piscina e barbecue valgono il soggiorno.

The Owl: view, pool and garden
Ein unvergesslicher Aufenthalt im Herzen der Toskana! Die Wohnung liegt traumhaft schön in der Natur – umgeben von sanften Hügeln, Weinbergen und unzähligen Olivenbäumen, die in der Sonne silbern schimmern und das Landschaftsbild einfach magisch machen. Die Aussicht ins Tal ist atemberaubend schön – man könnte stundenlang einfach nur dastehen und schauen. Der 28 Meter Pool? Besser geht es nicht – perfekt gelegen mit Panoramablick, absoluter Ruhe und einer Atmosphäre, die zur puren Entspannung einlädt. Was diesen Ort aber wirklich besonders macht, sind die Menschen: Jacopo, Sophia und ihre Kinder haben uns mit einer so herzlichen Offenheit empfangen, dass wir uns sofort wie bei guten Freunden gefühlt haben. Es ist einfach schön, solchen Menschen zu begegnen – authentisch, warm und voller Lebensfreude. Und dann war da noch Luba, die Schäferhündin – ein echtes Herz auf vier Pfoten! Sie hat uns jedes Mal mit solcher Freude empfangen, dass wir sie sofort ins Herz geschlossen haben.

Casa di Lyndall - Entire house with exclusive pool
Wir hatten eine wunderbare Woche in Lyndalls Haus in Lecchi in Chianti! Das Grundstück, das Haus und der Pool waren sogar größer und schöner als erwartet. Die Landschaft ist traumhaft – perfekt zum Entspannen. Die Küche war hervorragend ausgestattet, sodass wir fast jeden Tag gekocht haben. Auch die Restaurant-Empfehlung im Ort war ein Volltreffer. Wir haben uns rundum wohlgefühlt und würden jederzeit gerne wiederkommen. Vielen Dank, Lyndall!

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!

Supersuite con vista mozzafiato nel 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.

SUITE BOBO Relax nel Chianti Classico Gallo Nero
Licio ha sido de los mejores anfitriones que he tenido en Airbnb. Todo genial. Además me enamoré de su casa, el pasaje y todo Chianti. Espero volver!

Paluffo Stillo House
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!
Apartment 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.

Stone House in Chianti with pool
Monica and Sandro are great hosts. We felt home right away. Their recommendations in the near area were all great. They know really great restaurants and places to buy olive oil nearby. And they always helped us when we needed some ideas on what to do or where to go. The home is on a calm hill in the middle of olive trees. We liked the place a lot. It was very hot during our stay so the pool helped to cool down during the daytime. We can fully recommend the place and enjoyed our two week stay. We will come back...

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.

Villa La Loggia 1.0
We hebben enorm genoten van ons verblijf. Jonathan heeft ons super warm ontvangen en ons rondgeleid. Enorm mooi appartement, die heel mooi gedecoreerd was. Jonathan gaf ons ook enkele tips mee om uit te eten en Firenze te bezoeken. Dankjewel!

House between Firenze, Arezzo, chianti e Siena
Nous avons été de suite sous le charme de cette propriété. Tout ici compose l'image qu'on peut se faire de la belle campagne Toscane. Tout en haut de la colline surplombant la vallée, la vue y est splendide et romantique. La propriété a été renovée avec le confort d'aujourd'hui tout en conservant son âme d'autrefois. On s'y sent de suite bien, l'energie est bienfaisante, la nature, les animaux, tout est en harmonie! L'accueil, la cuisine d'Oscar, la superbe piscine, la terrasse ombragée, les petits-dejeuners copieux fait maison! C'est plus qu'un coup de coeur, cet endroit est une pépite! Nous reviendrons!

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.

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.

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!
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
Notre séjour se termine malheureusement demain et c’était bien Au delà de nos attentes🙏🏻 La Villa était exceptionnelle, propre, confortable avec une vue spectaculaire sur les Plaines du Chianti❤️ La Villa, la piscine, les fleurs, les plantes, la nature qui nous entourait, nous a permis de profitez de nos vacances bien au delà de tout ce que nous avions put imaginer! Notre hôte ,Signore Boncorso , a rendu notre séjour inoubliable grâce à son accueil exceptionnel et ses précieux conseils! Grazie mille! Une note parfaite! 5 étoiles xxxxx Un 5 Étoiles ⭐️⭐️⭐️⭐️⭐️ et plus!

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!

Il Poggetto by Interhome
Beautiful location in the country side. Perched on top of the hill with 360 degree views of surrounding vine fields. We even got to see them harvesting the grapes.

Villa di charme sulle colline del Chianti
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.

Poggio de'Galli by Interhome
We spent the most wonderfull 2 weeks here in this beautifull location. Hosts were the most helpfull, warm and friendly. Any troubles or questions we had, they helped and answered quickly. Their olive oil is also tasty, we can recommend it. The home was as pictured, clean and even in hot days relatively cool. Very lovely accommodation and the views were spectacular. Pool was a great joy during hot days. Location is great. We did not have a car rented but managed still to get around nicely. There is a short, about 15 minute hike to the bus stop to go to Florence but it is managetable when you reserve enough time. There is also a supermarket on the bus route which was great. Taxi from Florenze was not a problem. Getting a taxi here to go to Florence is harder and we recommend calling the taxi service and avoiding the application. This is if you are planning not to have a car. A wonderfull stay all in all. Highly recommend!

Villa il Palagio nelle campagne toscane
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!!

Suite Casa Luigi con piscina esclusiva
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.
Quick stats about holiday rentals with a pool in Grassina
Total rentals
50 properties
Nightly prices starting at
$102 SGD 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