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Holiday rentals with a pool in Grassina

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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 stars4 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 Certaldo

4.77 out of 5 average rating, 124 reviews

Lovely apartment in Chianti region

PauloRating, 5 stars4 months ago
What a lovely hidden gem, after a few days in busy Rome Giovanni places was exactly what we needed for a few days of relaxation. Closer to Pisa and Florence the apartment has everything we needed and the swimming pool was a bonus, so peaceful and clean. Giovanni very helpful and his home made bottle of wine was a lovely gesture. For certain one our favourite places we been this time in Italy.
Guest favourite

Home in Figline e Incisa Valdarno

5 out of 5 average rating, 26 reviews

Villa Siveri - private swimming pool - air con

SarahRating, 5 stars5 months ago
Great stay. The host is amazing do thoughtful responsive and kind. Gave my kids presents and a cooked for us. Just the most thoughtful can’t describe her as a host in any other ways. The only problems we encountered was the air conditioning in two of the rooms and a hard time getting to the house. Ask her to send you her exact location bc we got super lost.
Superhost

Home in Reggello

4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars4 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!
Guest favourite

Home in Pistoia

5 out of 5 average rating, 8 reviews

Countryside Cottage with Pool "Il Melograno"

CansuRating, 5 stars5 months ago
Everyone was wonderful, the accommodation was as described and the pool completely to ourselves. Giovanni was always super friendly and his family very accommodating. We would definitely recommend this location.
Superhost

Home in Cipressino

5 out of 5 average rating, 7 reviews

Countryside house with private pool and garden

MathiasRating, 5 stars4 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.
Superhost

Home in Firenze

4.79 out of 5 average rating, 67 reviews

Little Italy Planet : sweet house with Jacuzzi

CiroRating, 5 stars3 weeks ago
Very serious and responsive host, apartment equipped with all comforts. Ideal location to reach the center of Florence by bus in about 25 minutes. Easy to find parking on white stripes. Highly recommended.
Guest favourite

Home in Certaldo (Fi)

4.87 out of 5 average rating, 60 reviews

Paluffo Torre House

ShelbyRating, 5 stars6 months ago
My family of 5 including an infant, toddler and teen, had the best time at il Paluffo. It is a stunning property, the natural pool is unique and refreshing, they offer a ton of activities, local recommendations, and communication was always easy. Claudia, the manager, simply the best! She recommended us an amazing public pool in the hills of Tuscany, great for kids, and suggested some of the best places to eat nearby. It felt like she always had our best interest at heart. We would absolutely stay here again and will recommend to everyone we know!

Condo rentals with a pool

Superhost

Condo in Cavriglia

4.88 out of 5 average rating, 146 reviews

Chianti La Pruneta, Michelangelo apartment

JessRating, 5 stars3 months ago
Thanks for a fantastic few days Massimo! I don't think we could have picked a better place for our Tuscany holiday. The view of the valley was beautiful and the apartment was the perfect size for us two! The cooking class was amazing and we really loved the wine tasting at the local wineries as well.
Guest favourite

Condo in San Gimignano

4.95 out of 5 average rating, 123 reviews

Adalberto Apartment inside the Manor of Fulignano

NoniRating, 5 stars3 months ago
10/10 and we couldn't recommend it highly enough! Stunning location with the most picturesque view. The accommodation was well equipped, with everything we needed for our stay. Giovanni provided wonderful local recommendations from nearby towns - we will absolutely be coming back next time we are in Tuscany!
Superhost

Condo in Castelfranco di Sopra

4.83 out of 5 average rating, 232 reviews

House between Firenze, Arezzo, chianti e Siena

VasundharaRating, 5 stars3 months ago
Splendid location and excellent food! Perfect getaway in my opinion — I saw the prettiest sunset of my life surrounded by cats and ducks.
Guest favourite

Condo in Volterra

4.95 out of 5 average rating, 21 reviews

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

JanRating, 5 stars6 months ago
Wonderful place, very nice host. Thank you for your hospitality, Silvia
Guest favourite

Condo in Poggibonsi

4.73 out of 5 average rating, 253 reviews

PODERE VAL DI GALLO CHIANTI SIENA

JamieRating, 5 stars4 months ago
Loved our stay here. The property is beautiful and Silvia is a wonderful helpful host. We had everything we needed for us and our baby for a peaceful cozy stay.
Superhost

Condo in Castellina in Chianti

4.77 out of 5 average rating, 235 reviews

The Chianti House - IlVillinoFarmhouse

RebeccaRating, 5 stars3 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 stars17 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 stars3 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.

Home rentals with a private pool

Home in San Casciano V.Pesa (FI)

4.83 out of 5 average rating, 23 reviews

Ambrogetta by Interhome

Marte BergitteRating, 5 stars3 months ago
Very beautiful house and a dreamy view of Tuscany! Perfect home for us adults and children. But you need a car to get to the bakery. Nice restaurants close by.
Guest favourite

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 186 reviews

Stone House with Exclusive Pool Codilungo in Chianti

LeeRating, 5 stars3 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 stars8 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
Guest favourite

Villa in San Miniato

4.88 out of 5 average rating, 40 reviews

Villa with exclusive pool

AylaRating, 5 stars6 months ago
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. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

Home in Pieve a Presciano

5 out of 5 average rating, 3 reviews

Casavecchia by Interhome

NickRating, 5 stars16 months ago
Great holiday typical Toscan atmosphere.I strongly recommend,
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 stars3 months ago
We spent some nice autumn days at Francesca's place. It's much nicer than it's pictured. 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 go on 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 stars4 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

Suite Casa Luigi with exclusive pool

DanielleRating, 5 stars4 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 !!

Quick stats about holiday rentals with a pool in Grassina

  • Total rentals

    50 properties

  • Nightly prices starting at

    $113 AUD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    20 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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