Ossaia Villas with Pool

Excellent 1539 Guest Reviews 4.65 /5

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Total Results: 427


Villa Lavinia: Swimming Pool, Property, Natural Landscape, Sunlounger, House, Outdoor Furniture, Leisure, Real Estate, Estate, Vacation 0% Interest Installments € 574 - € 672/night

Superb independent villa with private pool, WIFI, A/C, hot tub and TV

  •   12
  •   5
  •   3
: EAS182280
€ 574 - € 672per Night

Description

Property Summary
Podere Villa Lavinia is a charming vacation rental located at the gates of Chianti. The property comprises two houses accommodating eight and four people respectively, both equipped with kitchens. Enjoy the amenities including a swimming pool, yard, internet WiFi, and parking facilities. The manor house, known as 'Villa Lavinia,' enjoys a sunny position just 1 km from the center of Montevarchi, Italy.

Outdoors
Guests of Podere Villa Lavinia can revel in the shared 10-hectare fenced garden, offering privacy and serenity. Relax in your own private garden or take a dip in the seasonal swimming pool (8 x 4 meters, 135 cm depth), available from April 8th to October 28th. Unwind on the garden furniture or fire up the barbecue for an alfresco dining experience.

Other Information
The holiday rental provides conveniences like reception, WiFi, and heating (November 1st to April 15th). Access the property via a 200-meter unmade road, and park your vehicles in the roofed parking area on-site. Soak in the hot tub after a day of exploring the nearby attractions.

Distances and Attractions
Podere Villa Lavinia is ideally situated near charming locales like Cavriglia, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Siena, and Montalcino. It's just 5 km from the Montevarchi railway station and 39 km from the Rapolano Terme thermal baths. This vacation rental offers a tranquil retreat while being close to local attractions, making it perfect for those seeking a rejuvenating getaway. Villa Lavinia

Tegliaia: Water, Cloud, Sky, Plant, Property, Swimming Pool, Blue, Tree, Shade, Rectangle 0% Interest Installments € 249 - € 456/night

Pretty independent accommodation with private pool, A/C, WIFI, TV, patio and panoramic view

  •   10
  •   5
  •   5
: EAS186599
€ 249 - € 456per Night

Description

Property Summary
La Tegliaia is a traditional Tuscan stone house divided into two separate apartments that can accommodate up to six people. This vacation rental in Montevarchi, Italy, offers a Swimming Pool, Yard, Internet Wifi, and Parking. The property is a beautiful detached country house situated in a secluded panoramic position, surrounded by olive trees on the eastern side of Chianti.

Outdoors
The property features a fenced swimming pool measuring 5 x 10 meters with a depth of 140 cm, available seasonally from May 27th to September 15th. Outdoor amenities include an arbor measuring 20 m2, a terrace, garden furniture, and a barbecue.

Other Information
The house is equipped with a central heating system, a washing machine, and heating is available from November 1st to April 15th, which must be paid on the spot. The property is accessible via a narrow motor road.

Distances and Attractions
La Tegliaia is located in the countryside, 5 km from the center of Montevarchi, 45 km from Siena, and 50 km from Florence. The nearest grocery store is 2 km away, and the shopping center is 5 km away. Nearby attractions include Montegonzi, Bucine, Gaiole in Chianti, Castello di Meleto, Radda in Chianti, and Castellina in Chianti. Tegliaia

Il Canto Del Maggio: Swimming Pool, Landscaping, Garden, Outdoor Furniture, Eco Hotel, Resort, Villa, Backyard, Evergreen 10% Off Discount  Special Offer € 65 - € 255/night

Fantastic home with WIFI, pool, A/C, TV, patio, pets allowed and panoramic view

  •   6
  •   14
  •   6
  •   6
: EAS213742
€ 65 - € 255per Night
  Accommodation
La Castellana 2 1 1
Canto al Sole 2 1 1
Bellina 2 1 1
Canto alla Luna 4 1 1
Lilla 2 1 1
Cecilia 2 1 1
14 6 6

Description

Hospitality, Osteria "Gentile" with veg garden, Cooking School and a stunning infinity pool overlooking the valley: il Canto del Maggio, owned by Simona and her family, isn’t just a place to sleep — it’s a place where you meet a family deeply rooted in this land and in its rhythms.

Here guests are welcomed into six charming units that reflect a rare and authentic form of hospitality: the Albergo diffuso—literally, a ‘scattered hotel’. Developed in Italy, this model revitalizes once-abandoned villages by blending comfort with local tradition in a truly immersive experience- in fact the "borgo" is a shared community between locals that live here permanently, and travelers that was born in the late 1980's.

Our collaboration with this placa was born to promote a network of local chefs, farmers, winemakers, guides, and hospitality professionals — all working together to create meaningful moments that we hope will make your stay one to remember.
My team (I am Tuscany) and I will take care of the accommodation side of your experience — from the moment you book to the day you arrive. Before your stay, we’ll coordinate with you to plan any extra services or personalized experiences, so everything is ready and tailored to your needs before you arrive.
Simona, the soul of this place, will welcome you into her world: her home, her kitchen, around her table, or walking through the vegetable garden — the orto. On the plate, a cuisine that arises spontaneously: the garden decides the menu, and we simply follow its lead.

Together, we can plan special dinners in the garden or by the pool, enjoy breakfast on the terrace or your private patio, and explore much more — from local farmers’ markets and tastings to our favorite go-to places in the area.

Available experiences include:
-Harvesting ingredients directly from the garden and discovering the joy of simple, farm-to-table cooking
-Themed culinary workshops (vegetarian, pastry-making, regional cuisine)
-Activities that immerse you in the natural beauty, culture, and traditions of the area
-Private meals (including breakfast) served anywhere on the property
-Pop-up events hosted by the restaurant or the outdoor kitchen
-Private events and retreats tailored to your needs Il Canto Del Maggio

Poggio Cuccule: Water, Cloud, Sky, Property, Plant, Swimming Pool, Blue, Azure, Tree, Rectangle 0% Interest Installments € 310 - € 787/night

Private Holiday home with private pool, WIFI, TV, balcony, pets allowed, panoramic view

  •   16
  •   8
  •   6
: EAS188813
€ 310 - € 787per Night

Description

Property Summary
Poggio Cuccule, a beautiful stone house from the late 1700s, offers the perfect vacation rental for those seeking relaxation and immersion in the stunning natural surroundings of Montegonzi, near Montevarchi, Italy. The manor house boasts a fenced-off 7,000m2 plot, complete with a private swimming pool, yard, internet wifi, and parking. Accommodating up to 16 guests, it provides ample space for large groups or families to unwind.

Outdoors
Surrounded by olive groves, vineyards, and woods, Poggio Cuccule offers a panoramic view of the countryside that will leave you captivated. The property features a private swimming pool (6x12m), garden furniture, barbecue, and fireplace, creating an idyllic setting for outdoor enjoyment and alfresco dining.

Other Information
The property is situated in a quiet, sunny, and elevated position, accessible via a steep, unmade road (200m), necessitating a car for convenient transportation. Linen is changed weekly, and room cleaning services are available upon request for an additional fee. Guests also have the option to hire a cook to prepare delicious meals during their stay, allowing them to savor the flavors of the region.

Distances and Attractions
Conveniently located just 7km from Montevarchi, Poggio Cuccule is in close proximity to shops, grocery stores, and public transportation. Nearby attractions include the Moto Cross Circuit Miravalle and the town of Cavriglia, offering opportunities for exploration and adventure. Additionally, local farm products are available for purchase on-site, allowing you to indulge in the flavors of the countryside during your holiday rental stay. Poggio Cuccule

Caggiolo: Blue, Swimming Pool, Shade, Landscaping, Eco Hotel, Outdoor Furniture, Resort, Hacienda, Backyard, Villa 0% Interest Installments € 130 - € 272/night

Amazing holiday home with WIFI, A/C, pool, TV, patio, pets allowed and panoramic view

  •   4
  •   2
  •   2
: EAS213632
€ 130 - € 272per Night

Description

Property Summary
Caggiolo is a cozy and comfortable terraced house surrounded by picturesque meadows and vineyards. Nestled in a tranquil countryside setting, it offers a shared swimming pool (fenced and available seasonally from June 1st to September 30th, with designated pool hours from 9 AM to 8 PM), an outdoor shower, a terrace, garden furniture, and parking for two cars. This charming vacation rental provides amenities such as a yard, internet WiFi, and is conveniently located near shops, groceries, supermarkets, restaurants, and bakeries within a 5 km radius.

Outdoors
Enjoy the serene outdoor spaces at Caggiolo. Relax by the shared swimming pool, which is fenced for your safety and available seasonally from June 1st to September 30th, with designated pool hours from 9 AM to 8 PM. An outdoor shower allows you to freshen up after a refreshing dip. Unwind on the terrace, furnished with comfortable garden furniture, and soak in the beautiful surroundings of meadows and vineyards. The property also offers a yard, perfect for enjoying the fresh air and sunshine.

Other Information
Caggiolo is part of a residence comprising 6 houses, ensuring a peaceful and intimate setting. The property is conveniently located 5.5 km from the center of Monteroni d'Arbia and 9 km from the center of Buonconvento. It is well-equipped with baby equipment, making it suitable for families with children. The owner/gardener oversees the pool maintenance, ensuring a clean and well-maintained environment for your enjoyment.

Distances and Attractions
Caggiolo is situated in a prime location, with various amenities and attractions within easy reach. Shops, groceries, supermarkets, restaurants, and bakeries are just 5 km away, while the bus stop "SR 2 Cassia" is 1000 km from the property. The railway station "Monteroni d'Arbia" is conveniently located 5 km away. For those seeking beach time, the sandy beach "Marina di Grosseto" is 80 km away, and the thermal baths "Rapolano Terme" are 39 km from the property. Golf enthusiasts can enjoy an 18-hole golf course located 28 km away, while tennis courts are available 5 km from the property. Walking paths can be accessed directly from the house, stretching 100 m. Nearby attractions include the charming towns of Montalcino (20 km), Siena (20 km), and Pienza (36 km), offering a glimpse into the rich history and culture of the region. Caggiolo

San Donnino: Property, Swimming Pool, House, Building, Real Estate, Home, Villa, Residential Area, Estate, Leisure € 76 - € 315/night

Cosy flat with WIFI, pool, patio and panoramic view, close to Siena

  •   7
  •   31
  •   13
  •   11
€ 76 - € 315per Night
  Accommodation
San Donnino 1 5 2 2
San Donnino 2 2 1 1
San Donnino 3 2 1 1
San Donnino 4 5 2 1
San Donnino 5 7 3 3
San Donnino 6 6 2 2
San Donnino 7 4 2 1
31 13 11

Description

Seven spacious, charactaristic apartments that have been tastefully and meticulously restored, located in a large farmhouse that was once a medieval Church. The farmhouse has a beautiful interior court yard, and about 50 m away is a completely renovated barn. Located south of Siena on the edge of the Crete Senesi, the property enjoys a tranquil, panoramic position inside a large farm (400 hectares) that produces wine and olive oil. Magnificent view of the countryside, characterized by the rolling hills of the Val D’Orcia and the city of Siena on the horizon. The apartments are furnished in a comfortable, rustic style. Outside, guests may use a charming, partially covered terrace (110m2) with a beautiful view.
The property can also be rented in its entirety for small groups, in which case guests may use a large, shared common room with kitchen.
Access to the property is via a 3 km unpaved but well-maintained road.
Distances: Ville di Corsano with small supermarket, restaurant/pizzeria, bar, post office, bus stop (Siena) 3,8 km away, Siena 19 km, Radda in Chianti 52 km, San Gimignano 62 km away, Arezzo 63 km, Volterra 67 km away, Florence (airport) approx. 90 km, Marina di Grosseto (beaches) 89 km away, Pisa (airport) approx. 180 km, Rome 250 km away.
At guests’ disposal: large oval swimming pool (12 x 16 m - depth 1,4 m / 1,8 m – open from 16/05 to 30/09) in a sunny, panoramic position, shower, 5 bicycles. Wi-fi internet and laundry room (outdoor) available. Covered parking within the grounds.
Extra services to be paid on the spot: Baby bed (free of charge). Maid service available upon request (€ 12,- / hour). It is possible to rent a large common room (30 people) with kitchen (large oven, dishwasher, freezer) and bathroom with shower ((price on request) accessible from outside or through apartments Donnino 1 and 5.

Please carefully check if there are any extra costs to be paid on site! San Donnino

Montevarchi 613: Water, Plant, Sky, Swimming Pool, Building, Tree, Shade, Rectangle, Body Of Water, Leisure   Special Offer 0% Interest Installments € 87 - € 188/night

Unique multi-unit villa with WIFI, A/C, pool, TV, patio and pets allowed

  •   2
  •   8
  •   2
  •   2
€ 87 - € 188per Night
  Accommodation
Le Poggiole 613.1 4 1 1
Le Poggiole 613.2 4 1 1
All 2 Accommodations 8 2 2

Description

Property Summary
Le Poggiole is a large working farm located in the picturesque countryside of Montevarchi, Italy. It features two apartments in the residence, making it an ideal vacation rental for families and groups. The property boasts a range of amenities to ensure a comfortable stay, including a swimming pool, yard, internet WiFi, parking, and the option for an installment plan. Guests can also purchase farm products from the local sale and enjoy the company of the owner, who resides on the premises.

Outdoors
The farm offers guests shared use of a 6-hectare fenced area, complete with trees, meadows, and a stunning 16 x 7 m swimming pool with depths ranging from 130 to 250 cm. The pool is available seasonally from May to September and is maintained by the owner/gardener. Additionally, there is an outdoor shower and barbecue area for guests to enjoy.

Other Information
The property also features a restaurant and a washing machine for shared use (extra fee applies). Heating is available from November to April and can be paid on the spot. Breakfast is available upon request (extra fee applies). Access to the property is via a 100 m long bumpy motorway, and parking is available on the premises.

Distances and Attractions
Le Poggiole is conveniently located near various attractions, including a shop (3 km), supermarket (6 km), railway station (8 km), outdoor swimming pool (3 km), indoor swimming pool (3 km), 9-hole golf course (60 km), tennis court (5 km), and riding stable (3 km). Please note that a car is recommended to explore the area. Montevarchi 613

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