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Holiday rentals with a pool in Grassina

Find and book unique homes with a pool on Airbnb

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 €70 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

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • 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

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
Home
4.99 out of 5 average rating, 104 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

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, 339 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

Superhost
The swimming pool glimmers under a partially cloudy sky, surrounded by lush olive trees and vegetation. Sun loungers are positioned nearby, offering space for relaxation, while a stone wall provides a rustic backdrop, enhancing the serene atmosphere of the outdoor area.
Apartment
4.83 out of 5 average rating, 224 reviews

Poggiolieto Suite - 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 typical Tuscan country house surrounded by olive trees. The Suite is a flat apartment (bedroom, living room with a sofa bed, bathroom and kitchen). 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.

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
4.88 out of 5 average rating, 814 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.

Guest favourite
A refreshing swimming pool is situated on a wooden deck, surrounded by lush greenery. The clear blue water reflects the bright sky, dotted with fluffy white clouds. In the background, a picturesque hillside is visible, providing a serene countryside view.
Home
4.84 out of 5 average rating, 284 reviews

Old barn The Nepitella Firenze

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.

Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage
4.98 out of 5 average rating, 210 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

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, 221 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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
The kitchen area features wooden cabinetry and a dining table surrounded by chairs. A traditional chandelier hangs from the ceiling. The room includes a stove, sink, and a television on a wooden sideboard, with decorative items and local artwork adorning the walls.
Home
4.95 out of 5 average rating, 128 reviews

Casa Nespolo – 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, microwave, coffee machine, sink and utensils. Available daily, for breakfast you will find coffee/tea, milk, biscuits and cakes. IT'S RECOMMENDED TO HAVE A CAR TO REACH THE HOUSE!

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, 473 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 serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.
Flat
4.86 out of 5 average rating, 271 reviews

Countryhouse 9 kms to Florence-3+2,free park, wine

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)

Guest favourite
Holiday home
4.89 out of 5 average rating, 315 reviews

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment

Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower
4.95 out of 5 average rating, 214 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Popular amenities for Grassina rentals with a pool