Vacation rentals with a pool in Province of Siena

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Top-rated rentals with a pool in Province of Siena

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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

Oct. 31 – Nov. 7

$720 CAD per night

Guest favourite

Farm stay in Montepulciano

4.96 out of 5 average rating, 136 reviews

Separate room, between Cortona and Montepulciano

We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

Mar. 7 – 14

$135 CAD per night

Guest favourite

Apartment 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.

Oct. 17 – 24

$138 CAD per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 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. Here time passes slowly according to ancient traditions. 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, original and working fireplace, parking free, WI-FI internet.

Feb. 24 – Mar. 3

$1,094 CAD per night

Guest favourite

Home in Rietine

4.85 out of 5 average rating, 185 reviews

Gaiole in Chianti Poggio Casabianca

We invite you in the heart of Chianti area. Poggio Casabianca is a little family homestead located in the Chianti Classico region exactly in the hearth of Tuscany. The owners live here and they offer at their guests an apartment with a big living room-kitchen with a big door that open directly to the garden, a bathroom with shower and a confortable doublebed room. Outside in the garden ther is a pool, shared with the owner, where you can refreshing and relaxing during the summer.

Oct. 11 – 18

$173 CAD per night

Guest favourite

Apartment in Caminino

4.92 out of 5 average rating, 129 reviews

Pieve di Caminino Historic Farm

The ancient Pieve di Caminino farm, now organic, is an important historical site: a former medieval village at the intersection of two ancient Roman streets, it hosted two saints (the 12th century church is now a private museum, which can be visited by guests by appointment). Today it covers 200 acres of gated private property, located on a scenic hill. Seven homes share an estate with a (seasonal) pool, two ponds, a century-old olive grove, vineyard, and a cork forest.

Mar. 14 – 21

$222 CAD per night

Guest favourite

Apartment 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.

Apr. 23 – 30

$210 CAD 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.

Nov. 1 – 8

$139 CAD per night

Guest favourite

Loft in Siena

4.94 out of 5 average rating, 194 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

Dec. 3 – 10

$322 CAD per night

Guest favourite

Farm stay in Castelnuovo dei Sabbioni

4.92 out of 5 average rating, 301 reviews

Chianti La Pruneta, Raffaello Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Oct. 24 – 31

$205 CAD per night

Guest favourite

Condo in arezzo

4.97 out of 5 average rating, 198 reviews

Esplora la natura al centro di Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Feb. 17 – 24

$405 CAD per night

Guest favourite

Cottage in Montagnano

4.93 out of 5 average rating, 116 reviews

Charming cottage in Tuscany

Charming cottage located on a hill overlooking 360 degrees. Oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ area Inside the room with French bed, living room with sofa bed, bathroom, kitchenette and indoor and outdoor dining space. Ideal for couples and families with one/two children. Cot available

Nov. 9 – 16

$169 CAD per night