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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
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.
Apartment
5 out of 5 average rating, 307 reviews

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.

Guest favourite
Apartment
4.9 out of 5 average rating, 127 reviews

New, bright, cozy Florence apartment with view

Hi! welcome to my bright and new apartment. You will have at your disposal: keyless opening (only 2 clicks); Fiber WI-FI; air conditioning; sofa bed; TV ; balcony (top floor overlooking Fiesole and the dome of the cathedral in the distance) and a full kitchen. Going down with the lift, the Tramvia will take you to the SMN central station in 8 min and the airport in 12 min. With 3 min walk, a large park and a shopping center for fun,eating well,shopping,groceries, training and a Low-cost parking

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.
Apartment
4.98 out of 5 average rating, 127 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
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
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
An open living space features exposed wooden beams and warm light from a large window. A kitchen area includes wooden cabinetry and appliances, while a dining table is set with chairs nearby. A sofa adds comfort to the room's inviting layout.
Barn
4.9 out of 5 average rating, 124 reviews

Charming ex. heybarn

A restored ex. hey-barn has a spacious bedroom, a bathroom and a kitchen.Access to the entrance is by a open "piazza" that also is the access to one of our other apartments. By a small staircase is the dedicated outdoorspace, table and chairs. The shared pool is open approx. end May to end September, time may vary. Heating system ONLY with wood-stove, handeld by guest.Not included in the rent a local tourist-tax; 2 euro/day/person over 14 years, the tax has to be paid in cash.

Guest favourite
Home
4.97 out of 5 average rating, 108 reviews

“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
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
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.
Apartment
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.
Flat
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.
Flat
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)

Top guest favourite
The suite features a spacious bed positioned against a decorative wall, complemented by a free-standing bathtub nearby. A window allows natural light to fill the room, showcasing the charming stone wall that adds character to the space.
Farm stay
4.99 out of 5 average rating, 102 reviews

Charming Farmhouse Suite

Tenuta Barosi, Isabella Suite - Experience the charm of Tenuta Barosi, a newly renovated agriturismo in 2024. Perched on a hilltop amidst olive groves, this serene retreat in Malmantile, a medieval village near Florence, offers stunning views and modern comforts.

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 £59 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 of Grassina holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grassina rentals

  • 4.7 Average rating

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