
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.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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

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.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

The Castle of 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.

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.

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)

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)

Old Barn very close to Florence
Antico fienile indipendente immerso nel verde della campagna ,vicinissimo a Firenze e al Chianti ,con piscina condominiale estiva. (apertura 08/06 al 08/09) Cucina soggiorno e giardino al piano terra con un bagno, al primo piano camera matrimoniale dalla quale è necessario passare per accedere a una cameretta con tre letti, uno dei quali a castello. Sempre al primo piano è presente il secondo bagno.

Podere Guidi
Apartment in a panoramic villa between Florence and Siena in the heart of the Chianti region in a charming village. The swimming pool is open from 1 May to 30 September, from 9 am to 1 pm, with exclusive use for guests during these hours. For different needs, ask the host.

Farmhouse near Florence - Fienile
Our farmhouse, called Podere Vignola, is an original Tuscan farmhouse. It is surrounded by Chianti vineyards and it a very quiet and relaxing place but yet very close to Florence and a ideal place for those willing to explore the beauty of Tuscany.
Popular amenities for Grassina rentals with a pool
House rentals with a pool

Ancient Barn in Chianti with Pool

Romantic Tuscan Retreat • Pool&Views

Relaxation and charm in the Chianti hills

Villa of the Hydrangeas

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Ancient Tuscan Rural Residence

Villino Arancio - plunge pool with Duomo view

BOBO SUITE Relax in the Chianti Classico Gallo Nero
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Romantic Apartment with Pool in Chianti

Stone House in Chianti with pool and parking

Adalberto Apartment inside the Manor of Fulignano

Casa Rebecca with a small private pool

House between Firenze, Arezzo, chianti e Siena

Ginestra: Private Pool Overlooking Florence

New, bright, cozy Florence apartment with view
Home rentals with a private pool

Sole by Interhome

Ambrogetta by Interhome.

Stone House with Exclusive Pool Codilungo in Chianti

Casa Bensa by Interhome

Il Poggetto by Interhome

Podere San Lorenzo by Interhome

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive 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 € 68 per night before taxes and fees

Verified guest reviews
Over 1,380 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Grassina holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Grassina rentals

4.8 Average rating
Grassina stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Flat rentals Grassina
- Rentals with a fireplace Grassina
- House rentals Grassina
- Rentals with a patio Grassina
- Family-friendly rentals Grassina
- Rentals with a washing machine and dryer Grassina
- Pet-friendly rentals Grassina
- Rentals with outdoor seating Grassina
- Rentals with pools Metropolitan City of Florence
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Ponte Vecchio
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
- Mugello Circuit
- Castiglion del Bosco Winery
- Basilica of Santa Croce




