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Vacation rentals in Castell'In Villa

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Top-rated vacation rentals in Castell'In Villa

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 504 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 133 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
Villa in Chianciano Terme
4.97 out of 5 average rating, 125 reviews

Villa with View for Family & Friends, in Tuscany

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top guest favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 152 reviews

Villa di Geggiano – Guesthouse

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. 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 idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Guest favorite
Villa in Castell'In Villa
5 out of 5 average rating, 7 reviews

Villa marielena chianti farnhouse - villa marielen

Villa Marielena is a beautifully restored Tuscan farmhouse located in the prestigious Castel in Villa area of Gaiole in Chianti, one of the most renowned wine regions in Italy. Surrounded by vineyards and olive groves, the villa offers privacy, panoramic views, and direct access to the landscapes that make Chianti famous. The property enjoys a privileged position for exploring Tuscany’s wine country. The vibrant town of Castelnuovo Berardenga is only 8 km away, while Siena and many of ...

Guest favorite
Castle in Tignano
4.96 out of 5 average rating, 24 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Guest favorite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.9 out of 5 average rating, 124 reviews

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 150 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Guest favorite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay in Cavriglia
4.92 out of 5 average rating, 366 reviews

Chianti La Pruneta, Raphael 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.

Guest favorite
A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.
Farm stay in Gaiole in Chianti
4.94 out of 5 average rating, 254 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Top guest favorite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.98 out of 5 average rating, 213 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Top guest favorite
Farm stay in Siena
4.97 out of 5 average rating, 315 reviews

Authentic Tuscan Country House WITH A/C

L'appartamento "Pergola" (75 mq), è una delle due unità abitative indipendenti che compongono l'agriturismo Terra Rossa, situato nel cuore della campagna senese a pochissimi minuti di macchina dal centro storico.

Popular amenities for Castell'In Villa vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Castell'In Villa