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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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Home in Montespertoli

4.84 out of 5 average rating, 69 reviews

Holiday immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a holiday immersed in the Tuscan countryside, with a large swimming pool 🌞💐equipped with the scents of nature, breathtaking landscapes and the pool will be the setting for the relaxation you are looking for. 🚴🏻Are you feeling the urgeto move around? Then you can swim, walk, or run through the paths around your country house 🏃. 🏛The strategic location of the apartment allows you to make excursions to Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style. "

Guest favourite

Cottage in Castiglion Fibocchi

5 out of 5 average rating, 38 reviews

Castellin di Bocco Tuscan countryhouse with pool

A pochi chilometri da Arezzo la casa è parte di un edificio che risale al 1623. Completamente isolata ma a pochi km da Arezzo Una splendida e ampia piscina è a disposizione e allieterà le calde giornate. Sviluppata su due livelli ha tre camere da letto e due bagni, una cucina attrezzata che affaccia su una terrazza-giardino, due ampi salotti dotati di smart tv, wifi Per gli amanti dell'avventura e dello sport, è possibile noleggiare e-bike e percorrere i sentieri che si snodano tra le colline.

Guest favourite

Flat in Gaiole In Chianti

4.76 out of 5 average rating, 21 reviews

Idyllic with shared pool in the heart of Chianti

Beautiful Gaiole, home of vintage bike-race Eroica, rolling hills with vineyards. Apt in prizewinning complex, lovely shared pool. Perfect for a family (1 bedroom). Discount for longer stays. NB: We ONLY rent to guests with good reviews. Apt: Kitchen, 1 bedroom (dbl + bunk). Lovely village w/ plenty of great restaurants incl michelin-star. No pets/smoking/parties! Shared pool, ping pong, gym. Fee for linen + A/C will be asked in advance. AC in the bedroom is not working, service is ordered.

Home in San Casciano in Val di pesa

4.83 out of 5 average rating, 89 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Guest favourite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Guest favourite

Flat in Montaione

4.98 out of 5 average rating, 40 reviews

Exclusive villa Lionella with private pool

Villa Lionella is an exclusive residence within 2 hectares of private park with swimming pool and independent entrance and private parking. It consists of a large living room with fireplace, dining room, kitchen with second fireplace, library with sofa bed. Upstairs 5 bedrooms with 3 bathrooms. In the basement billiard room, poker table, fitness area with sauna. Equipped with air conditioning, WiFi, linen and private pool. The villa is for the exclusive use of those who book it only

Villa in Poppi

4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Borgo Sereno is a small, ancient hamlet recently restored with art and passion, brought back to life respecting its original characteristics and masterfully turned into a splendid and unique holiday home for large groups. The property is located within a large private area on the green hill of the Casentino Forest National Park between Florence and Arezzo, only 4 km from the ancient medieval town of Poppi which was mentioned as one of the most beautiful towns in Italy.

Guest favourite

Villa in Siena

4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

Truthful Tuscan paradise just 12mins from Siena. Boasting two doubles and two twins, 3 bathrooms, a very large leaving room, a beautiful dining room with fire place, park, parking and pool are all private. It is the ideal old and authentic family retreat, nestled on top of the Montechiaro hill with 360 degrees views over Chianti. The host leaves in the adjacent house. In winter and early spring there is an extra charge of 50€ a day for heating.

Guest favourite

Loft in Scandicci

4.98 out of 5 average rating, 100 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and last floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location to explore Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation in the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees...and remember that all the vegetables of the Valline garden are at your disposal!

Villa in Monsummano Terme

4.8 out of 5 average rating, 5 reviews

Panoramic Farmhouse with Pool and Amazing Views

Nestled on the enchanting hills of Monsummano Terme, Le Due Terre Farmhouse, this contemporary yet timeless Tuscan farmhouse embodies the perfect blend of rustic charm and modern luxury. With breathtaking views that stretch across the rolling Tuscan landscape, every corner of this property exudes elegance and tranquility.<br><br>The centerpiece of this idyllic retreat is the panoramic pool, offering an oasis of relaxation.

Guest favourite

Flat in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

Unique experience in a real, old Tuscan farmhouse. Podere Casa Muricce is the place for people who love nature, animals, woods, but also close to the main places of interest in Tuscany. Situated on the top of a hill high 400mt, carefully restructured according to the tradition, Casa Muricce is the typical ancient Tuscany house in stone: all the furnishings, even doors, are original from Tuscany houses of `700/'800.

Guest favourite

Townhouse in Barberino Tavarnelle

4.96 out of 5 average rating, 81 reviews

Tower dating back to 1212 in the heart of Tuscany

In the heart of Tuscany, newly renovated apartment in old farmhouse restored from the ground up. Only 30 minutes from Florence and 40 from Siena. A/C in every room and screens on door and windows Extremely quiet, with all comforts including a common infinity pool with large private umbrella for shade. Relax outside with a glass of wine or tour around chianti from this conveniently located home.

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Popular amenities for Grassina rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Fiesole

4.97 out of 5 average rating, 30 reviews

Scenic country house with large pool near Florence

Guest favourite

Home in Civitella in Val di Chiana

4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

Guest favourite

Home in Figline e Incisa Valdarno

5 out of 5 average rating, 26 reviews

Villa Siveri - private swimming pool - air con

Home in Reggello

4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

Guest favourite

Home in Reggello

5 out of 5 average rating, 42 reviews

Villa in Tuscany - Reggello, with pool and WiFi.

Guest favourite

Home in Pistoia

5 out of 5 average rating, 8 reviews

Countryside Cottage with Pool "Il Melograno"

Home in Cipressino

5 out of 5 average rating, 7 reviews

Countryside house with private pool and garden

Guest favourite

Home in Volterra

5 out of 5 average rating, 8 reviews

Authentic farm vacation 10 km from the city

Apartment rentals with a pool

Guest favourite

Apartment in San Gimignano

4.95 out of 5 average rating, 123 reviews

Adalberto Apartment inside the Manor of Fulignano

Guest favourite

Apartment in Volterra

4.95 out of 5 average rating, 21 reviews

Three-room apartment with 2 bedrooms and private garden, pool

Guest favourite

Apartment in Poggibonsi

4.73 out of 5 average rating, 253 reviews

PODERE VAL DI GALLO CHIANTI SIENA

Apartment in Castellina in Chianti

4.77 out of 5 average rating, 235 reviews

The Chianti House - IlVillinoFarmhouse

Apartment in Gavinana

5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

Guest favourite

Apartment in San Casciano in Val di Pesa

4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

Apartment in Gambassi Terme

4.89 out of 5 average rating, 45 reviews

Panoramic apartment with pool and private garden

Apartment in Fiesole

4.88 out of 5 average rating, 178 reviews

Poggiolieto Studio - on hills 10' from city center

Home rentals with a private pool

Home in San Casciano V.Pesa (FI)

4.83 out of 5 average rating, 23 reviews

Ambrogetta by Interhome

Guest favourite

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 186 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Home in Poggibonsi

4.5 out of 5 average rating, 4 reviews

The Nest by Interhome

Home in Fucecchio

5 out of 5 average rating, 3 reviews

Casale il Poggio by Interhome

Guest favourite

Villa in San Miniato

4.88 out of 5 average rating, 40 reviews

Villa with exclusive pool

Guest favourite

Home in San Casciano in Val di pesa

5 out of 5 average rating, 41 reviews

Charming villa in the Chianti hills

Guest favourite

Villa in Pian di SCO

5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

Guest favourite

Home in Tavarnelle Val di Pesa

4.93 out of 5 average rating, 92 reviews

Casa Luigi Suite with Exclusive Pool

Quick stats about holiday rentals with a pool in Grassina

Total rentals
50 properties
Nightly prices starting at
₹6,063 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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