Holiday rentals with a pool in Casole d'Elsa

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Top-rated rentals with a pool in Casole d'Elsa

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Guest favourite

Home in Localita' Pievescola

4.93 out of 5 average rating, 147 reviews

Antico Borgo Ripostena – no. 8 Casa Vecchia

Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning. PRIVACY: EACH APARTMENT HAS A PRIVATE ENTRANCE AND TERRACE FOR TOTAL PRIVACY CLEANING: APARTMENTS ARE DISINFECTED WITH CERTIFIED EQUIPMENT BEFORE EACH ARRIVAL POOL: EACH APARTMENT HAS A DESIGNATED SPACE RESERVED AT THE POOL. SMART SERVICES: WEB CHECK-IN

20–27 Apr

$289 SGD per night

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 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

6–13 Apr

$845 SGD per night

Guest favourite

Apartment in Noce

5.0 out of 5 average rating, 126 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!

15–22 Nov

$196 SGD per night

Guest favourite

Flat in Caminino

4.92 out of 5 average rating, 130 reviews

Pieve di Caminino Historic Farm

L'antica fattoria Pieve di Caminino, oggi biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due antiche strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

1–8 Jan

$211 SGD per night

Guest favourite

Holiday home in Casole d'Elsa (SI)

4.92 out of 5 average rating, 175 reviews

Off the beaten path Tuscan Farmhouse, great views

Away from it all in the heart of Tuscany, Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. Perfect for couples and older families to relax, recharge or work remotely, the apartment has a private entrance and garden with outdoor seating area and a private rooftop balcony - stunning views, fantastic sunsets and big night skies. There are two other independent apartments on the olive farm that share the pool and private parking.

28 Sep – 5 Oct

$202 SGD per night

Guest favourite

Farm stay in Provincia di Siena

4.99 out of 5 average rating, 148 reviews

Agriturismo La Villa - Il Castagno, Pool & Garden

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

3–10 Oct

$560 SGD per night

Guest favourite

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.

1–8 Mar

$406 SGD per night

Guest favourite

Cottage in Chianni

4.98 out of 5 average rating, 118 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3)

14–21 Feb

$220 SGD per night

Guest favourite

Cottage in Lucardo

4.99 out of 5 average rating, 216 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).

20–27 Jan

$366 SGD per night

Guest favourite

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.

30 Nov – 7 Dec

$221 SGD per night

Guest favourite

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.

23–30 Sep

$1,148 SGD per night

Guest favourite

Apartment in San Gimignano

4.95 out of 5 average rating, 110 reviews

Adalberto Apartment inside the Manor of Fulignano

Nella campagna di San Gimignano, in antica fortificazione risalente all'anno 1000 ora dimora di campagna, situata su di un colle con veduta panoramica, affittasi bellissimo appartamento di ca. 60mq con vista su San Gimignano e sui vigneti circostanti

21–28 Apr

$181 SGD per night