Vacation rentals with a pool in Asciano

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Asciano

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 196 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Guest favorite

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Guest favorite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 191 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Guest favorite

Villa in Siena

4.89 out of 5 average rating, 274 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet. In winter and early spring there is an extra charge of 40€ a day for heating.

Guest favorite

Home in Castellina in Chianti

4.98 out of 5 average rating, 104 reviews

StageROOM03 -Chianti Idillic Country living

This beautiful country house is located in the Borgo di Tuopina, a hamlet overlooking the Chianti hills, only 10 mins drive from Siena and Castellina in Chianti. This original Tuscan country house has been completely renovated in 2019 and boasts 2 bedrooms, 2 bathrooms, TV, a fully equipped kitchen with a dishwasher, two fridges and a washing machine. The outdoor marble hot-tub allows you to fully relax while enjoying the amazing views of the surroundings.

Guest favorite

Castle in Ferrano

4.99 out of 5 average rating, 182 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.

Guest favorite

Cottage in Lucardo

4.99 out of 5 average rating, 238 reviews

Best view ever & private pool

Antique Tuscan barn made into a comfortable home with private swimming pool. Best views ever. Close to Florence, Siena and Pisa. Very quiet, yet easy to reach. Sunsets you can only dream of. Ideal Tuscan getaway for family or two couples. The house has two bedrooms and two bathrooms plus a guest bathroom on the ground floor. The pool has a panoramic edge and whirlpool section. There are two restaurants on walking distance (a few hundred meters).

Guest favorite

Loft in Siena

4.95 out of 5 average rating, 219 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Guest favorite

Rental unit in Carpineto

4.96 out of 5 average rating, 157 reviews

Tuscany Countryside, Peace & Relax 10 min from Siena

Our accommodation is close to Siena, so to the nightlife, the city center but also to the small airport of Ampugnano, the parks, and public transport. You'll love our place because of the light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our place is good for couples, sole adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favorite

Tower in Fiesole

4.94 out of 5 average rating, 181 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.

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 358 reviews

Old hayloft on the Chianti hills

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. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Guest favorite

Home in Asciano - Chiusure - Monte Oliveto Maggiore

4.96 out of 5 average rating, 176 reviews

Country House in the Crete Senesi

County house deep into the natural reserve that surrounds the village of Chiusure and the Abbey of Monte Oliveto Maggiore. Intimate oasis of relax with private garden and pool located in the heart of Siena's area between Val d'Orcia and Crete Senesi