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Vacation 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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Home in Florence

4.89 out of 5 average rating, 724 reviews

TREEhouse/casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the Duomo and 30' from Siena. Come and live with us; enjoy our olive trees, the kitchen garden and our family life style away from the working rhythm. By providing wifi only in the communal courtyard we suggest our guests to utilize internet only when is really needed. Taking a break from been connected with elsewhere and enjoy the 'here and now' could be our best present to you!

Aug 28 – Sep 4

G$63,578 GYD per night

Condo in Noce

5.0 out of 5 average rating, 127 reviews

Vergianoni estate nestled in the Chianti with a pool

Podere Vergianoni is located in the beautiful hills of Chianti. The apartment is furnished in perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and unique, handcrafted furniture. Inside you will find a large living room with kitchen ,sofa bed , a bathroom and a bedroom with double bed. In the large outdoor courtyard you will find at your disposal a swimming pool on a breathtaking terrace where you can enjoy a wonderful view of the view with unique sunsets!

Jan 5 – 12

G$29,108 GYD per night

Apartment in Fiesole

4.84 out of 5 average rating, 178 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.

Feb 7 – 14

G$23,396 GYD per night

Condo in Strada in Chianti

4.94 out of 5 average rating, 325 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

Your separate apartment in our secluded 12th century farmhouse has its own entrance and is on two levels; kitchen and sitting area is on the first floor, beds and bath are upstairs. The large fireplace in the kitchen is very typical in these old houses. In the sleeping rooms we have air conditioning. The garden is unique , a place to relax and enjoy. If there is no available date check out our second new listing, same property, "Chianti Patio Apartment" Pleased to welcome you!

Feb 9 – 16

G$21,845 GYD per night

Home in Strada In Chianti

4.96 out of 5 average rating, 114 reviews

BOBO RELAX SUITE in Chianti Classico Gallo Nero

This is a beautifulapartment located a few kilometers from Florence (19km) where you can enjoy a completely private panoramic pool....not shared with anyone... The accommodation is a recently renovated open space consisting of entrance hall, kitchen, bathroom with hydromassage , bedroom...the TV is also with Netflix. The tourist tax of € 1.50 per person from 14 years onwards...up to 7 consecutive days..and in the period from June 1 to October 31 the rate is €2.00

Oct 28 – Nov 4

G$16,214 GYD per night

Castle in Ferrano

4.99 out of 5 average rating, 162 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.

Mar 25 – Apr 1

G$61,046 GYD per night

Bed and breakfast in Pelago

4.92 out of 5 average rating, 206 reviews

DELUXE Tenuta Risalpiano Room

Our deluxe rooms are ideal for couples stays, couples with children who want to enjoy the beauty of the hills. Thanks to their large size ranging from 23 to 26 square meters, they can have triple occupancy with the addition of a third bed. The rooms are equipped with a private bathroom with shower and bidet, closet or closet room with dresser to store clothes in complete safety. Among the comforts, TV, Wi-Fi, courtesy kit, minibar (for a fee).

Oct 11 – 18

G$30,533 GYD per night

Apartment in La Presura

4.91 out of 5 average rating, 109 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)

Apr 7 – 14

G$30,713 GYD per night

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 311 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Nov 30 – Dec 7

G$34,003 GYD per night

Home in Bagno a Ripoli

4.94 out of 5 average rating, 102 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.

Oct 18 – 25

G$21,890 GYD per night

Tower in Fiesole

4.95 out of 5 average rating, 153 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.

Sep 23 – 30

G$175,478 GYD per night

Apartment in Pontassieve

4.91 out of 5 average rating, 171 reviews

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.

Jan 14 – 21

G$73,677 GYD per night

Vacation rentals for every style

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Popular amenities for Grassina rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Certaldo

4.91 out of 5 average rating, 110 reviews

Paluffo Stillo House

Apr 10 – 17

G$72,569 GYD per night

Home in San Martino

4.95 out of 5 average rating, 176 reviews

Casa Bada - Barn

Feb 28 – Mar 7

G$54,989 GYD per night

Home in Florence

4.81 out of 5 average rating, 227 reviews

Old barn The Nepitella

Mar 13 – 20

G$43,765 GYD per night

Home in Florence

4.88 out of 5 average rating, 137 reviews

Il Melograno, Florence hills & pool & olive oil

Dec 24 – 31

G$34,558 GYD per night

Home in Sorana

4.96 out of 5 average rating, 243 reviews

Tuscan Nature Views From Casa Gave

Jan 8 – 15

G$19,803 GYD per night

Home in Casale

4.86 out of 5 average rating, 153 reviews

Infinity view

Nov 8 – 15

G$103,189 GYD per night

Home in Terranuova Bracciolini

4.96 out of 5 average rating, 105 reviews

Villa Lolù with private heated swimming-pool

Sep 28 – Oct 5

G$136,701 GYD per night

Home in Barberino Val D'elsa

4.97 out of 5 average rating, 103 reviews

Podere Villetta La Colombaia

Jan 11 – 18

G$27,938 GYD per night

Condo rentals with a pool

Condo in Florence

4.93 out of 5 average rating, 138 reviews

VILLA LE PERGOLE - Florence

Jul 11 – 18

G$57,767 GYD per night

Condo in arezzo

4.97 out of 5 average rating, 198 reviews

Explore Nature in Downtown Chianti Vigneti

Dec 30 – Jan 6

G$55,278 GYD per night

Condo in San Gimignano

4.95 out of 5 average rating, 110 reviews

Adalberto Apartment inside the Manor of Fulignano

Apr 17 – 24

G$27,777 GYD per night

Condo in Castellina In Chianti

4.78 out of 5 average rating, 287 reviews

relaxation among the vineyards of Chianti1-IlVillinoFarmhouse

Oct 22 – 29

G$30,053 GYD per night

Condo in Castelnuovo dei Sabbioni, caviglia

4.89 out of 5 average rating, 122 reviews

Chianti La Pruneta, Michelangelo apartment

Sep 12 – 19

G$28,594 GYD per night

Condo in Greve in Chianti

4.86 out of 5 average rating, 149 reviews

ROSA cosiest and romantic studio

Oct 19 – 26

G$23,079 GYD per night

Condo in Rignano sull'Arno

4.81 out of 5 average rating, 120 reviews

Panoramic apartment, WiFi, swimming pool, terrace

Oct 19 – 26

G$36,125 GYD per night

Condo in Casole d'Elsa

4.93 out of 5 average rating, 124 reviews

La Casetta

Dec 27 – Jan 3

G$44,170 GYD per night

Home rentals with a private pool

Cottage in San Filippo A Ponzano

4.98 out of 5 average rating, 172 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Apr 16 – 23

G$88,745 GYD per night

Home in San Casciano in Val di pesa

4.82 out of 5 average rating, 74 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Oct 28 – Nov 4

G$158,946 GYD per night

Home in Tavarnelle Val di Pesa

4.92 out of 5 average rating, 73 reviews

Casa Luigi Suite with Exclusive Pool

Sep 10 – 17

G$51,059 GYD per night

Home in Pescia

4.77 out of 5 average rating, 13 reviews

Aurora by Interhome

Apr 12 – 19

G$76,093 GYD per night

Villa in San Miniato

4.86 out of 5 average rating, 37 reviews

Villa with exclusive pool

Apr 28 – May 5

G$90,383 GYD per night

Villa in San Casciano in Val di pesa

5.0 out of 5 average rating, 29 reviews

Charming villa with pool in the hills of Chianti

Oct 24 – 31

G$94,424 GYD per night

Home in Greve in Chianti

5.0 out of 5 average rating, 16 reviews

Casa 360 by Interhome

G$97,560 GYD per night

Villa in Casino di Terra

4.81 out of 5 average rating, 62 reviews

Private Retreat in Tuscan Countryside

Sep 9 – 16

G$89,710 GYD per night

Quick stats about vacation rentals with a pool in Grassina

Total rentals
50 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
G$16,721 GYD before taxes and fees

Destinations to explore