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Holiday rentals with a pool in Grassina

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grassina

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
A vintage-styled kitchen and dining area feature a small wooden table with colorful chairs, accompanied by a bicycle and a wall-mounted television. Kitchen appliances include a microwave and a minimalist cabinetry design. Natural light filters through a balcony door, opening to a garden view.
Condo in Scandicci
4.95 out of 5 average rating, 120 reviews

Appartamento Vintage con Piscina nel Chianti

Located at the first floor of LeVallineBed&Boutique complex, the Santa Croce apartment is the "writer's refuge". Enhanced by a vintage style, the two-room apartment, thanks to the sofa bed, can accommodate up to four people. Located in an ideal position for discover the Tuscany country side and Chianti is 15/20 minutes by car from Florence city center. Be inspired by it's particular atmosphere, walk among the olive trees until you reach the outdoor bio swimming pool, heated in the spring months.

Superhost
A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.
Home in Galluzzo
4.88 out of 5 average rating, 808 reviews

TREEhouse/casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.

Top Guest favourite
A private garden area is showcased, featuring a mini pool with a sleek white exterior. Two soft seating cushions are positioned nearby on wooden decking, under a shaded pergola. Lush green foliage surrounds the space, providing a serene atmosphere for relaxation.
Condo in San Marco
4.97 out of 5 average rating, 116 reviews

Garden & SPA -FlorArt Boutique Apartment

Elegante appartamento in palazzo d’epoca a pochi minuti a piedi dalle principali attrazioni d’arte, di ristorazione e dalla Stazione Centrale. Terrazza abitabile con giardino e vasca con funzione mini piscina, camera matrimoniale collegata a sala da pranzo con divano letto matrimoniale, bagno, cucina. Ambiente raffinato e curato in ogni minimo dettaglio. Appena fuori da ZTL con vista campanile di Giotto. Collegamento diretto con aeroporto, stazione e centro tramite la linea della tramvia T2

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 300 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

Top Guest favourite
A rustic dining area is highlighted by a long wooden table surrounded by several chairs. A vase of sunflowers sits at the center. The stone wall adds warmth to the space, while a clock and decorative items provide an inviting touch.
Home in Bagno A Ripoli
4.96 out of 5 average rating, 160 reviews

Casetta Melograno - Cozy farmhouse in Chianti

This house is part of an old building recently refurbished and in the past was a convent which used to be a part of the castle estate located in front of us. The interior design reflects the typical Tuscan style of furniture and materials. The kitchen is equipped with a fridge, induction hob, microwave, coffee machine, sink and utensils. Available daily, for breakfast you will find coffee/tea, milk, biscuits and cakes. it's recomended to have a car to reach the accomodation and to move.

Guest favourite
A serene outdoor seating area features white iron chairs adorned with floral cushions, set against a rustic stone wall. A nearby tree provides shade, surrounded by greenery and a view of the countryside, creating a peaceful spot for relaxation.
Home in Galluzzo
4.84 out of 5 average rating, 276 reviews

Old barn The Nepitella

The Antico Fienile La Nepitella in Florence is the perfect place for a vacation. You will find a residence immersed in the Tuscan landscape, just 15 minutes by car from the center of Florence and an hour from Siena. You will be surrounded by greenery and tranquility, with views of the historic Certosa dell'Ema, for a dream vacation. Three bus lines to Florence are nearby, and it is located 20 minutes from the Chianti region. It is a secluded corner, away from the usual tourist routes.

Guest favourite
A stone-built house is set against a backdrop of rolling hills. A crystal-clear swimming pool is surrounded by wooden decking. Lush greenery frames the scene, with tall pine trees and manicured gardens enhancing the landscape's natural beauty.
Home in Strada In Chianti
4.97 out of 5 average rating, 108 reviews

House “il colle”.nice house surrounded by vineyard

Da una porzione di casa colonica abbiamo ricavato un piccolo e grazioso appartamento. Il giardino è in parte esclusivo ed in parte in comune con la mia famiglia che vive nella’ altra parte della casa . La piscina è ad uso esclusivo degli ospiti. Il proprietario Gregorio , amante dello sport, offre gratis tour in bicicletta nella campagna toscana!!! Circondata da vigneti e bosco offre una situazione di estrema pace . Distante pochi minuti dal centro di Strada in Chianti

Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 210 reviews

Il Castello di Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Superhost
An open space studio with a dining area is visible, featuring a table set for a meal. Above, a loft area houses a spacious bed, while wooden stairs lead to it. Natural light enters through windows, highlighting the rustic decor and inviting ambiance.
Condo in Fiesole
4.86 out of 5 average rating, 198 reviews

Poggiolieto Studio - on hills 10' from city center

Poggiolieto is on the hills just 10 minutes far by car from the Historical center of Florence. The property is a tipical Tuscan country house surrounded by olive trees. The Studio is a two levels open space apartment; swimming pool in spring and summer time; private parking. The house is in a strategic location to be close enough for visiting Firenze's artistic city centre, but be in the peace of the countryside at home with garden and swimming pool.

Guest favourite
A tranquil outdoor pool is surrounded by well-maintained gardens and olive trees. Sun loungers are positioned along the poolside, providing space for relaxation. The stone-clad building in the background complements the landscape, contributing to the serene environment.
Apartment in La Presura
4.93 out of 5 average rating, 161 reviews

Country house 9 km to Florence-2+1g,free parking

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

Top Guest favourite
An outdoor swimming pool is framed by stone tiles and lush greenery, with a few umbrellas offering shade nearby. The serene atmosphere is enhanced by olive trees and cypress lining the background, creating a relaxing retreat surrounded by nature.
Apartment in La Presura
4.91 out of 5 average rating, 110 reviews

Farmhouse 9 kms to Florence-2+1

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

Popular amenities for Grassina rentals with a pool

Quick stats about holiday rentals with a pool in Grassina

  • Total holiday rentals

    Explore 50 holiday rentals in Grassina

  • Nightly prices starting at

    Grassina holiday rentals start at $139 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Grassina holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Grassina rentals

  • 4.7 Average rating

    Grassina stays receive an average rating of 4.7 out of 5 from guests