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Villa vacation rentals in Monte San Savino

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Top-rated villa rentals in Monte San Savino

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Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

LocationFamilyHiking

4.93 out of 5 average rating, 254 reviews
Guest favorite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

ValueLocationWifi

4.9 out of 5 average rating, 240 reviews
Top guest favorite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

FamilyValueGrill

4.97 out of 5 average rating, 125 reviews
Top guest favorite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme

Charming Tuscan Villa with View forFamily&Friends

The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away

LocationValueBreakfast

4.97 out of 5 average rating, 128 reviews
Top guest favorite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

FamilyLocationGrill

4.92 out of 5 average rating, 331 reviews
Guest favorite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

FamilyValueIndoor spaces

4.96 out of 5 average rating, 166 reviews
Top guest favorite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

La Vignaccia (Farmhouse) - villa w/private pool

Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.

FamilyLocationLong stay

4.96 out of 5 average rating, 101 reviews
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

LocationFamilyBreakfast

4.98 out of 5 average rating, 105 reviews
Top guest favorite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

FamilyLocationWalkability

4.97 out of 5 average rating, 158 reviews
Top guest favorite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

ValueLocationIndoor spaces

4.98 out of 5 average rating, 182 reviews
Top guest favorite
Villa in Arezzo

Tuscany View - Villa Arianna

This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience.  While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

LocationValueCheckout

4.99 out of 5 average rating, 122 reviews
Guest favorite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

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, airconditioned bedrooms, 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.

ValueLocationHeating

4.89 out of 5 average rating, 307 reviews

Popular amenities for Monte San Savino villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top guest favorite
The image showcases a rustic stone farmhouse surrounded by lush vineyards and olive trees. The building features a classic roof with terracotta tiles, set against a clear blue sky. Green grass frames the scene, emphasizing the natural beauty of the countryside.
Villa in Impruneta

Agriturismo Podere Scaluccia Chianti, Florence

FamilyLocationDecor

4.99 out of 5 average rating, 121 reviews
Top guest favorite
A serene pool area is framed by lush olive trees and a spacious lawn. Two lounge chairs are positioned by the edge of the inviting pool, with the house visible in the background, showcasing its traditional architecture and surrounding greenery.
Villa in Lucignano

Unique Villa in Tuscany

FamilyLocationQuiet

4.93 out of 5 average rating, 41 reviews
Superhost
A swimming pool is situated within a fenced area, surrounded by olive trees and greenery. The water appears clear and inviting, and a white umbrella offers shade on one side. A staircase leads into the pool, enhancing accessibility.
Villa in Monte San Savino

Il Cerreto - Tuscan Ancient House

ValueFamilyLaundry

4.9 out of 5 average rating, 82 reviews
Guest favorite
Villa in Monte San Savino

Private villa with pool

LocationFamilyComfort

5.0 out of 5 average rating, 12 reviews
Guest favorite
Villa in Arezzo

Coaching House

LocationFamilyGetting around

5.0 out of 5 average rating, 66 reviews
Top guest favorite
A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.
Villa in Sinalunga

Gli sterpi

FamilyLocationBathroom

5.0 out of 5 average rating, 97 reviews
Guest favorite
An outdoor dining area is presented under a wooden pergola, featuring a long table set for meals. Soft lighting is provided by hanging fixtures, and the surrounding lush greenery complements the rustic stone structure in the background.
Villa in Lucignano

Villa Eleonora

LocationFamilyComfort

4.82 out of 5 average rating, 17 reviews
Guest favorite
A two-story stone villa is surrounded by vibrant flower beds, featuring blooming geraniums and lush greenery. Tall trees provide a natural backdrop, while multiple windows adorned with shutters create an inviting facade. Steps lead to the entrance, offering access to the charming garden landscape.
Villa in Lucignano

Sasso Canaldo Villa: elegant Tuscan farmhouse

ValueFamilyWalkability

4.96 out of 5 average rating, 24 reviews

Luxury villa rentals

Guest favorite
Villa in Montepulciano

Villa a Montepulciano con Piscina

ValueFamilySleep quality

4.92 out of 5 average rating, 146 reviews
Top guest favorite
Villa in Cortona

Tuscan Villa Luigina with Pool & Panoramic View

FamilyLocationDecor

4.81 out of 5 average rating, 108 reviews
Top guest favorite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

LocationValueLayout

4.97 out of 5 average rating, 119 reviews
Guest favorite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo

Fabulous Farmhouse with Pool & 360 Panoramic View

FamilyLocationWifi

4.91 out of 5 average rating, 58 reviews
Top guest favorite
The aerial view captures the charming layout of Monticchiello, showcasing terracotta-roofed buildings surrounding a lush green garden adorned with soft lighting. A winding pathway leads to the garden, providing a serene outdoor area amidst the medieval architecture.
Villa in Monticchiello

Villa with garden. The Cardinal's Garden.

LocationFamilyBreakfast

4.98 out of 5 average rating, 95 reviews
Top guest favorite
Villa in Arezzo

Casa Napoleone - Tuscan Villa w/ pool near Cortona

FamilyLocationBathroom

4.96 out of 5 average rating, 27 reviews
Superhost
A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.
Villa in Pierle

Historic Villa Getaway with 6BR/9BA, Pool, Views

LocationFamilyPool

4.89 out of 5 average rating, 46 reviews
Guest favorite
A spacious villa is surrounded by lush countryside, featuring a well-maintained outdoor area with a swimming pool. Lounge chairs are arranged around the pool, and flowering trees and shrubs are visible. Nearby vineyards and rolling hills provide a scenic backdrop, enhancing the picturesque landscape.
Villa in Civitella in Val di Chiana

Villa with Pool Casa la Quiete

LocationFamilyBiking

4.9 out of 5 average rating, 94 reviews

Villa rentals with a pool

Guest favorite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino

Ortaglia di Sotto Farm

LocationFamilyKitchen

4.95 out of 5 average rating, 19 reviews
Top guest favorite
A charming brick farmhouse is framed by olive trees and lush gardens, providing a serene backdrop for the inviting pool. Sun loungers and umbrellas are arranged around the pool area, creating a relaxing outdoor space for guests to unwind.
Villa in Cortona

Villa Il Giardino di Diana (12 people)

LocationFamilyShared spaces

4.96 out of 5 average rating, 46 reviews
Top guest favorite
The image features a serene outdoor area with a spacious swimming pool surrounded by lounge chairs. Lush greenery and flowering plants line the poolside, while a stone wall and distant hills provide a peaceful backdrop under a clear sky.
Villa in Pieve a Socana

Villa Montanina - relax in esclusiva in Toscana

LocationFamilyShared spaces

4.99 out of 5 average rating, 83 reviews
Guest favorite
The spacious kitchen and dining area features rustic wooden beams and well-lit windows that invite natural light. A large dining table is surrounded by white chairs, accommodating several guests. An inviting seating area with a sofa and decorative elements enhances the communal atmosphere.
Villa in Arezzo

Tuscany Country House with swimming pool

ValueLocationPool

4.95 out of 5 average rating, 73 reviews
Superhost
A tranquil swimming pool is framed by sun loungers and umbrellas, offering a refreshing spot to relax. The villa is positioned above, showcasing its classic architecture and landscaped gardens, surrounded by lush greenery and blooming flowers.
Villa in Lucignano

Magnificent 1700's villa in Tuscany

ValueLocationLayout

4.81 out of 5 average rating, 67 reviews
Superhost
The exterior view of a single-story villa features a private pool surrounded by a wooden deck and several lounge chairs. A shaded portico with seating overlooks a garden filled with greenery and flowers, providing a serene outdoor space.
Villa in Arezzo

At Elena's

FamilyLocationComfort

4.65 out of 5 average rating, 17 reviews
Top guest favorite
A private swimming pool is surrounded by stone walls and olive trees. The inviting clear water reflects the blue sky. In the background, a rustic house with stone walls and a broad archway is visible, along with a pool house featuring a textured exterior.
Villa in San Giovanni d'Asso

Pasqui Villas : Tribbio private house pool WiFi

LocationFamilyView

5.0 out of 5 average rating, 37 reviews
Top guest favorite
An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.
Villa in Loro Ciuffenna

The Lazy Oak

LocationFamilyCheck-in

4.97 out of 5 average rating, 71 reviews

Destinations to explore