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.

0 of 0 items showing

1 of 3 pages

Superhost

Home in Montespertoli

4.83 out of 5 average rating, 70 reviews

Vacation immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a holiday immersed in the Tuscan countryside, with a large equipped swimming 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 you can swim, walk or run among the trails around your home in the countryside. 🏛The strategic location of the apartment allows excursions to Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style."

Guest favourite

Home in San Casciano In Val di Pesa

4.84 out of 5 average rating, 91 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 Cerbaia

4.9 out of 5 average rating, 21 reviews

Villanuova Power 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.

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.

Superhost

Serviced 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

Guest favourite

Flat in Le Piastre

4.93 out of 5 average rating, 28 reviews

Il Fienile, pool, hot tub, sauna, quiet located

These holiday accommodations consist of 6 apartments, tastefully furnished and each with a private terrace/garden area. This place is perfect for a relaxing holiday surrounded by nature. The property has large lawns surrounded by flowerbeds, a barbecue, a table tennis, a Jacuzzi as well as a sauna, and a swimming pool (11x5, open june-september). Nearby there is a stream along which one can take long walks. Wi-Fi connection at the reception. Welcome gift. Heating included.

Superhost

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.

Top guest favourite

Loft in Scandicci

4.98 out of 5 average rating, 106 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, 15 minutes by car from Florence and San Casciano! Take a moment to relax on the beautiful panoramic terrace over Florence, or cool off in the bio pool among olive trees...and remember that all the vegetables in the garden of the Villas are at your disposal!

Top 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.

Guest favourite

Farm stay in Gaiole in Chianti

4.97 out of 5 average rating, 100 reviews

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2

Beautiful charming 1 bedroom ground floor apartment in the Le Miccine villa. Surrounded by vines and nature. Ideal location for visiting Tuscany or relaxing by the pool. Wine tasting on site and helpful staff. We are classified as a 4 Sunflower Agriturismo.