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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 Montespertoli

4.84 out of 5 average rating, 69 reviews

Holiday immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped pool 🌞💐The scents of nature, the breathtaking landscapes and the swimming pool will be the setting for the relaxation you are looking for. 🚴🏻‍♂️🏃‍♀️Then if you feel the need to move around you can swim, walk, or run through the trails around your country home. 🏛The strategic location of the apartment allows you to hike in Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style.”

Apartment 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, 88 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.

Home in Cerbaia

4.9 out of 5 average rating, 21 reviews

Podere Villanuova 2

Cute apartment in the tuscan countryside with a beautiful pool, set in Cerbaia, 20 km away from Florence. It is in a great position to visit many of the highlights of Tuscany and the wine region of Chianti. We rent a small apartment that has a living room with kitchen, a main bedroom, one bathroom. The house has a beautiful and spacious garden with a big pool overlooking the tuscan hills. In the property there is the villa of the owners and another apartment that we rent here on airbnb.

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.

Apartment 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

Loft in Scandicci

4.98 out of 5 average rating, 98 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!

Apartment in Montespertoli

4.89 out of 5 average rating, 19 reviews

Cozy Apart. in Cottage,4/5people,SWPOOL,AIRCO,WIFI

2 double bedrooms (of which one may be changed with 2 or 3 single-beds), 2 full bathrooms, a livingroom with a working fireplace, a closet, a kitchen fully equipped with stove, fridge, freezer, dish-washer, microwave, moka (Italian Coffe-Maker), toaster, kettle, American-coffee-machine. Digital-Terrestrial-Television (DTT). Private heating. Private shady garden, equipped with BBQ, tables and chairs.Wi-Fi. FREE AIR-CONDITIONING!!

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.

Apartment 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.

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.

Apartment in San Gimignano

4.97 out of 5 average rating, 33 reviews

Spacious apartment for couples or families

Charming apartment in the countryside: from here you can enjoy the best view of the towers of San Gimignano It is a perfect accommodation for walking and relaxing. The Focolare, with an entrance from the outside stairs, is on the first floor of the house. The living room has a fireplace Full kitchen two bedrooms with double bed,with en-suite bathroom.

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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 Fiesole

4.97 out of 5 average rating, 30 reviews

Scenic country house with large pool near Florence

Home in Certaldo

4.77 out of 5 average rating, 124 reviews

Lovely apartment in Chianti region

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

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

Home in Firenze

4.78 out of 5 average rating, 64 reviews

Little Italy Planet : sweet house with Jacuzzi

Home in Certaldo (Fi)

4.87 out of 5 average rating, 60 reviews

Paluffo Torre House

Condo rentals with a pool

Condo in Cavriglia

4.88 out of 5 average rating, 146 reviews

Chianti La Pruneta, Michelangelo apartment

Condo in San Gimignano

4.95 out of 5 average rating, 123 reviews

Adalberto Apartment inside the Manor of Fulignano

Condo in Castelfranco di Sopra

4.83 out of 5 average rating, 232 reviews

House between Firenze, Arezzo, chianti e Siena

Condo in Volterra

4.95 out of 5 average rating, 21 reviews

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

Condo in San Casciano in Val di pesa

4.89 out of 5 average rating, 161 reviews

Belvedere

Condo in Castellina in Chianti

4.77 out of 5 average rating, 235 reviews

The Chianti House - IlVillinoFarmhouse

Condo in Gavinana

5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

Condo in San Casciano in Val di Pesa

4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

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

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

Villa in San Miniato

4.88 out of 5 average rating, 40 reviews

Villa with exclusive pool

Home in San Gimignano

4.75 out of 5 average rating, 4 reviews

Villa Alba by Interhome

Home in San Casciano in Val di pesa

5 out of 5 average rating, 41 reviews

Charming villa with pool in the Chianti hills

Villa in Pian di SCO

5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

Home in Tavarnelle Val di Pesa

4.93 out of 5 average rating, 92 reviews

Casa Luigi Suite with Exclusive Pool

Quick stats about vacation rentals with a pool in Grassina

Total rentals
60 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

Destinations to explore