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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 in Noce
5 out of 5 average rating, 292 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.

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.
Apartment in Scandicci
4.95 out of 5 average rating, 118 reviews

Vintage apartment with swimming pool in 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
4.89 out of 5 average rating, 805 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.
Apartment in San Marco
4.96 out of 5 average rating, 107 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 in Bagno A Ripoli
4.96 out of 5 average rating, 159 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 dining table is set under the shade of lush trees, featuring a bottle of wine and glasses. The surrounding garden is filled with tall cypress trees and vibrant greenery, creating a serene atmosphere for outdoor dining.
Farm stay in San Casciano In Val di Pesa
4.78 out of 5 average rating, 163 reviews

Sperone: two floors apartment with pool

Just a few km from Florence and surrounded by vineyards and olive groves of the Principe Corsini estate, this is the ideal place for a classic Tuscan-style holiday in the heart of Chianti Classico. The private garden, which also provides access to the pool at Villa Le Corti, is ideal for relaxing and peaceful al fresco dining. The pool, open from June to September, has a breathtaking view of Tuscan rolling hills. The property includes a parking area reached from the entrance gate.

Top guest favourite
A spacious living area is furnished with a dining table and four chairs, complemented by a cozy sofa. Large windows offer views of the surrounding landscape, while subtle natural light filters through textured shades. A television is mounted on the wall, with a glimpse of an elegant bathroom in the background.
Loft in Scandicci
4.98 out of 5 average rating, 127 reviews

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!

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

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.

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, 433 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.

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 in La Presura
4.92 out of 5 average rating, 160 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
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano
4.96 out of 5 average rating, 190 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Superhost
A warm and inviting fireplace is surrounded by various decorative elements, including potted plants and wall art. Baskets filled with logs are neatly arranged, enhancing the cozy ambiance. Natural light enters through nearby windows, creating a bright and comfortable space.
Home in Tavarnelle Val di Pesa
4.89 out of 5 average rating, 174 reviews

Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

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 $104 SGD 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!

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