Holiday rentals with a pool in Montalcino

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Top-rated rentals with a pool in Montalcino

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

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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

13–20 Apr

$846 SGD per night

Guest favourite

Home in Orvieto

5.0 out of 5 average rating, 181 reviews

Vineyards Paradise

Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

8–15 Apr

$486 SGD per night

Guest favourite

Serviced apartment in San Quirico d'Orcia

4.78 out of 5 average rating, 174 reviews

Studio apartment (2+1) in Val d 'Orcia - Tuscany

A few steps from the historic center of the medieval San Quirico d 'Orcia and just 100 meters from the supermarket, a stay made of silence and quiet passage of time, of days with a relaxing and refreshing atmosphere, characteristic of the lifestyle in Val d' Orcia. The Taste of Tranquility is guaranteed by a park of 5000 square meters that offers shady meadows and trees suitable for reading or simple rest. Ideal for a stay with an "ancient" flavor, combined with all the modern comforts.

21–28 Feb

$161 SGD per night

Guest favourite

Flat in Asciano

4.96 out of 5 average rating, 112 reviews

Loggiato 1 in farm stay with shared pool

Apartment for 2 people IN the Santa Lucia farm stay (farmhouse divided into 7 apartments) IN the Crete Senesi 10 km from Siena. Located on the first floor with a private coffee table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), bathroom with shower and living room with functional kitchen. Outdoor space with table and chairs on the ground floor. Paid air conditioning in the room according to consumption.

3–10 Oct

$132 SGD per night

Guest favourite

Flat in Caminino

4.92 out of 5 average rating, 129 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.

14–21 Mar

$215 SGD per night

Guest favourite

Flat in Laviano

4.95 out of 5 average rating, 100 reviews

Farmhouse with swimming pool with wonderful view

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eight vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

20–27 Apr

$205 SGD per night

Guest favourite

Farm stay in Murlo

4.99 out of 5 average rating, 136 reviews

Country house near Siena

The apartment is on the ground floor of a farmhouse of 1600, it is very cozy, the floors are in wood and the walls are painted in bright colors. The house consists of a large kitchen, a bedroom where there is also a sitting area with a comfortable sofa that can accommodate two people and a fireplace near the sofa. The house is surrounded by beautiful hills and woods. In front of the house there is a terrace where to eat, and a garden with deckchairs.

30 Dec – 6 Jan

$197 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

Flat in Montalcino

4.97 out of 5 average rating, 30 reviews

Studio Flat with pool for 2 people

The Paradise of Frassina offers accommodation in 1 charming apartment for your vacation in Montalcino. The apartment, the Studio, is furnished in a rustic style and equipped with all the comforts (private pool, parking, Wi-Fi, equipped kitchen, air conditioning, private outdoor space), the perfect place to relax listening to the harmonies of Mozart and taste a glass of Brunello, by the infinity pool overlooking the vineyards.

15–22 Oct

$199 SGD per night

Guest favourite

Home in Anghiari

4.99 out of 5 average rating, 196 reviews

Casa Rosmarino Eco-Wellness Country Home

Price Includes: - WELLNESS HOT TUB w/Jacuzzi Infrared SAUNA - FOOD & DRINKS 1 Welcome Aperitivo 1 Wine 1 Nespresso w/Capsules - COMFORT Heater 2 Night Included, Extra Night 25 Euro Shower Gel / Shampoo / Hair Dryers Bathrobes / Flips Flops Wood for the HotTub and Fireplace - EXTRA (not included) MASSAGES PASTA Making Class, Oil/Truffle/Wine TASTING Please INQUIRE for price & availability

3–10 Dec

$647 SGD per night

Guest favourite

Flat in Montalcino

4.99 out of 5 average rating, 80 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

1–8 Sep

$967 SGD per night

Guest favourite

Flat in Montalcino

4.89 out of 5 average rating, 323 reviews

Panoramic Country Suite Montalcino

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

13–20 Apr

$251 SGD per night