Some info is shown in its original language. Translate

Vacation rentals with a pool in Grassina

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Grassina

  • Total vacation rentals

    Explore 70 vacation rentals in Grassina

  • Nightly prices starting at

    Grassina vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

  • Verified guest reviews

    Over 1,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Grassina vacation rentals include wi-fi 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.

1 of 1 pages1 / 1
Top guest favorite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5 out of 5 average rating, 210 reviews

Antico Podere del 1600 nel Chianti in Toscana

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizi ed esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con stupenda vista su castello colline e vigneti con tramonti mozzafiato.

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.
Condo in Fiesole
4.83 out of 5 average rating, 225 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 in Galluzzo
4.88 out of 5 average rating, 815 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 favorite
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
4.95 out of 5 average rating, 175 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.

Top guest favorite
Home in Greve in Chianti
4.99 out of 5 average rating, 107 reviews

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

Guest favorite
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 in Galluzzo
4.84 out of 5 average rating, 285 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 favorite
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 in Barberino Tavarnelle
4.98 out of 5 average rating, 211 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.

Superhost
An underground heated pool is surrounded by rustic brick walls, featuring soothing green water and a gentle current. The ceiling has exposed brick, creating an inviting, natural atmosphere. The space offers privacy, ideal for relaxation and rejuvenation.
Home in Careggi
4.82 out of 5 average rating, 152 reviews

Country House w/ heated Pool near the City Centre

Nestled in a centuries-old park, this 16th-century house offers a serene retreat, just 15 minutes by tram from the city. The true gem is the underground heated pool at 31°C, complete with a jacuzzi and waterfall, providing moments of relaxation in total privacy. The 2 bright suites, 2 full bathrooms, kitchen, and living room welcome guests in an atmosphere of elegance. Upon request: Dinner with a private chef and free transfer to and from the airport and train station.

Top guest favorite
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, 222 reviews

Il Castello di 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 favorite
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, 475 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 favorite
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.
Apartment in La Presura
4.86 out of 5 average rating, 272 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 favorite
Vacation home in Dimezzano
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.

Popular amenities for Grassina rentals with a pool