Apartment vacation rentals in Radicondoli

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Top-rated apartment rentals in Radicondoli

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Top guest favorite

The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.

Apartment in Siena

Villa di Geggiano – Alfieri Suite

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

FamilyLocationHospitality

4.99 out of 5 average rating, 169 reviews

Guest favorite

Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.

Apartment in Asciano

Loggiato 2 Apartment in Tuscany with pool

The Loggiato 2 apartment for 2 people is located in the Santa Lucia farmhouse (THE FARMHOUSE IS DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is a two-room apartment located on the first floor with a private table in front of the windows of the entrance loggia. There is a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen and television. The apartment has air conditioning in the room (for a fee).

ValueFamilyDecor

4.94 out of 5 average rating, 161 reviews

Top guest favorite

A bright living room features a white sofa adorned with decorative pillows, positioned near a large window that opens to a terrace with panoramic views. Natural light floods the space, highlighting the rustic stone wall and simple coffee table with a vase of flowers.

Apartment in Radicondoli

Tuscan Hilltop Retreat | Views, Charm, Fireplace

Imagine waking up to rolling Tuscan hills, stepping onto your private terrace with a cup of coffee, and realizing you have nowhere else to be. No crowds, no tour buses—just church bells, the fragrance of home‑cooked food, and the peaceful rhythm of an authentic hilltop village. This 14th‑century stone duplex in Radicondoli sits at the heart of a real working village—not a tourist set piece—and puts you within easy reach of Siena, Florence, San Gimignano, and the Chianti wine region.

LocationFamilyBeach

4.98 out of 5 average rating, 51 reviews

Top guest favorite

A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.

Apartment in Montemassi

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

LocationFamilyCondition

4.98 out of 5 average rating, 129 reviews

Top guest favorite

The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.

Apartment in Siena

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

FamilyValueLayout

4.97 out of 5 average rating, 116 reviews

Top guest favorite

An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.

Apartment in Gavignano

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Guests have access to a furnished garden, free Wi-Fi, a shared swimming pool, a wood-burning oven, a barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse, recently renovated in the Tuscan tradition and divided into three comfortable apartments.

FamilyLocationRiver

4.92 out of 5 average rating, 390 reviews

Top guest favorite

The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.

Apartment in Montalcino

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.

ValueFamilyGetting around

4.99 out of 5 average rating, 118 reviews

Guest favorite

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

Apartment in Monteroni d'Arbia

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

LocationValuePets

4.94 out of 5 average rating, 288 reviews

Top guest favorite

An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.

Apartment in Monteriggioni

Comfort Apartment in the Chianti Vineyards

Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, kitchenette, a double bedroom, a private bathroom with shower, and air conditioning.

LocationFamilyBreakfast

4.93 out of 5 average rating, 455 reviews

Top guest favorite

An aerial view captures the medieval village of Certaldo, featuring terracotta rooftops and winding streets. The lush greenery surrounding the village adds a natural touch, while historic buildings stand prominently, showcasing varied architectural styles. The placement of the highlighted property is evident within the quaint atmosphere.

Apartment in Certaldo

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

LocationFamilyParking

4.98 out of 5 average rating, 138 reviews

Top guest favorite

A balcony provides a scenic view of Piazza del Campo, showcasing the surrounding historic buildings. A small table and chair invite relaxation, while the colorful sunset casts a warm glow over the area, highlighting the lively atmosphere with people enjoying the space below.

Apartment in Siena

A BALCONY ON THE PIAZZA OF THE PALIO

Three windows with balcony overlooking Piazza del Campo that allows access to an exclusive terrace with breathtaking views of the Piazza del Palio and the Palazzo Pubblico. One bedroom, large super-equipped kitchen. Sofa bed available to comfortably accommodate up to 4 people

LocationValueDecor

4.87 out of 5 average rating, 271 reviews

Top guest favorite

A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.

Apartment in Montalcino

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.

ValueLocationPool

4.9 out of 5 average rating, 406 reviews