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Holiday rentals with a pool in Grassina

Find and book unique homes with a pool on Airbnb

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Popular amenities for Grassina rentals with a pool

House rentals with a pool

Guest favourite
Home in Fiesole
4.97 out of 5 average rating, 30 reviews

Scenic country house with large pool near Florence

YvonneRating, 5 stars6 months ago
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.
Superhost
Home in Florence
5 out of 5 average rating, 4 reviews

New Florence "Afrodite" suite with pool

SarahRating, 5 stars3 days ago
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!
Superhost
Home in Reggello
4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars6 months ago
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!
Top Guest favourite
Home in Reggello
5 out of 5 average rating, 43 reviews

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.

MayaRating, 5 stars7 months ago
We were very pleasantly surprised! Perfect for a peaceful stay with a group. I absolutely recommend:)
Top Guest favourite
Home in Pistoia
5 out of 5 average rating, 8 reviews

Country Cottage with Pool "Il Melograno"

FedericaRating, 5 stars7 months ago
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
Superhost
Home in Cipressino
5 out of 5 average rating, 7 reviews

Countryside house with private pool and garden

MathiasRating, 5 stars7 months ago
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.
Guest favourite
Home in Certaldo
4.87 out of 5 average rating, 61 reviews

Paluffo Tower House

BrianRating, 5 stars6 days ago
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.
Guest favourite
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 136 reviews

Nada Home

JessicaRating, 5 stars1 week ago
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

Top Guest favourite
Condo in San Gimignano
4.95 out of 5 average rating, 124 reviews

Adalberto Apartment inside the Manor of Fulignano

DaveRating, 5 stars4 days ago
Great stay, incredible views, good location….
Guest favourite
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 453 reviews

Casa Rebecca with a small private pool

ValeriaRating, 5 stars1 week ago
Perfect accommodation to find peace and tranquility, the pool could not be used for temperatures but it is definitely a great comfort for the hottest days! Benedetta was a really hospitable and very kind host (as was her beautiful dogs!). Highly recommended to relax and enjoy peace in the middle of nature.
Superhost
Condo in San Gimignano
5 out of 5 average rating, 4 reviews

Apartment Melissa

StéphanieRating, 5 stars82 months ago
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.
Guest favourite
Condo in Volterra
4.95 out of 5 average rating, 21 reviews

Three-room apartment with 2 bedrooms and private garden, swimming pool

JanRating, 5 stars8 months ago
Wonderful place, very nice host. Thank you for your hospitality, Silvia
Superhost
Condo in Castellina in Chianti
4.77 out of 5 average rating, 235 reviews

The house in Chianti - IlVillinoFarmhouse

RebeccaRating, 5 stars6 months ago
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
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars19 months ago
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!
Guest favourite
Condo in San Casciano In Val di Pesa
4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

DavidRating, 5 stars6 months ago
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.
Superhost
Condo in Fiesole
4.88 out of 5 average rating, 180 reviews

Poggiolieto Studio - on hills 10' from city center

TheresaRating, 5 stars1 month ago
Very loving and sweet hosts. A very cozy and pretty accommodation. We liked it very much 🥰

Home rentals with a private pool

Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 187 reviews

Stone House with Exclusive Pool Codilungo in Chianti

LeeRating, 5 stars5 months ago
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.
Home in Poggibonsi
4.5 out of 5 average rating, 4 reviews

The Nest by Interhome

MartinRating, 5 stars10 months ago
"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. For excursions to the well-known area with San Gimignano, Volterra, Siena, Florence, etc., an ideal starting point. Highly recommended
Home in Fucecchio
5 out of 5 average rating, 3 reviews

Il Poggio Farmhouse by Interhome

NilsRating, 5 stars7 months ago
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!
Top Guest favourite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
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!
Top Guest favourite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 41 reviews

Charming villa in the Chianti hills

WilhelmRating, 5 stars5 months ago
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.
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
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!!
Guest favourite
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 92 reviews

Casa Luigi Suite with exclusive pool

DanielleRating, 5 stars6 months ago
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 !!
Home in Borgo San Lorenzo
4.86 out of 5 average rating, 7 reviews

The Barn by Interhome

PhilipRating, 5 stars11 months ago
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 holiday rentals with a pool in Grassina

  • Total rentals

    50 properties

  • Nightly prices starting at

    $126 AUD 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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