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Vacation rentals in Casole d'Elsa

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Top-rated vacation rentals in Casole d'Elsa

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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, 153 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
Condo in Casole d'Elsa
4.94 out of 5 average rating, 16 reviews

Dimora San Donato - Apt.1985

Dimora San Donato, located in the historic centre of Casole d'Elsa, combines refinement and elegance. The interiors, spacious with great attention to detail, offer a perfect blend between tradition and modernity. The location allows guests to immerse themselves in the daily life of the village, surrounded by a breathtaking landscape of rolling hills and centuries old cypresses. The Dimora represents a journey into the heart of Tuscany, where history, culture and natural beauty come together.

Top guest favorite
A sunny pool area is surrounded by lush greenery, featuring a rectangular swimming pool with a sunlit patio. Several green and white umbrellas provide shade over lounge chairs, inviting guests to relax in the outdoor space.
Condo in Casole D'Elsa
4.97 out of 5 average rating, 109 reviews

Manuela appartamento con piscina in agriturismo

Sarete ospitati in un appartamento situato al primo piano ,con ingresso indipendente e vi si accede salendo 17 scalini .E' composto da una cucina , due camere, una matrimoniale e una con 2 letti singoli , un bagno con doccia zanzariere alle finestre. Piccolo balcone condiviso con l'appartamento GIRASOLI. È OBBLIGATORIO PAGARE LA TASSA DI SOGGIORNO AL CHECK IN 1€ a persona per i primi 5 giorni . Riscaldamento consentito dal 1^ novembre al 15 aprile (Legge regionale)€ 20,00 al giorno

Superhost
A rustic stone building is framed by lush greenery, featuring large arched windows and wooden detailing. A paved pathway leads to the entrance, while outdoor furniture invites relaxation in the garden. The bright blue sky complements the tranquil countryside setting.
Cottage in Casole d'Elsa
4.79 out of 5 average rating, 24 reviews

Meadow view Cottage. Scenic pool + secret terrace

✅ 80 m² on 2 floors with equipped kitchen ,1 double bedroom + ensuite full bathroom, 1 bedroom with twin beds + ensuite full bathroom, both with airco. Private little garden +BBQ and secret patio...so many options for your daily meals or dinners under the stars! ✅ Glorious scenic pool ✅ 1 km walking to the medieval town Casole with restaurants and cafès ✅ Central location to visit many hidden gems +Unesco Heritage Sites Olivo Cottage is part of Monti 1824,composed of 6 units + pool

Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 339 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

Top guest favorite
A charming street in the historical center is lined with rustic brick buildings. Potted plants and flowers adorn the facades, while the pathway features a mix of smooth stone and tile. Overhead, the sky is partially cloudy, allowing natural light to illuminate the scene.
Apartment in Casole d'Elsa
4.97 out of 5 average rating, 32 reviews

Appartamento Mirella in centro storico

Comodo appartamento per 2-4 persone, in centro storico a Casole d’Elsa, con vista panoramica dalla terrazza sulle colline toscane. A 18 km da San Gimignano, 25 km da Volterra e 35 km da Siena. L’alloggio offre due camere, una matrimoniale e una doppia con letti singoli, bagno con doccia, sala da pranzo con divano e tv, cucina, terrazza, cantina, Wi-Fi, stanzino esterno con lavatrice. Parcheggio gratuito a 2 e 5 minuti a piedi, concesso il carico e scarico. CIN: IT052004C2R23DIUHK

Top guest favorite
An open-plan living area is shown, featuring warm, rustic décor with exposed wooden beams and terracotta flooring. A dining table for six is visible, alongside comfortable seating arrangements. The kitchen area, equipped with modern amenities, is integrated into the space, providing a welcoming atmosphere.
Apartment in Casole d'Elsa
5 out of 5 average rating, 37 reviews

Casa Vacanze "Anna" - IL MUSICISTA per 4-5 persone

“IL MUSICISTA” E' situato nel centro storico, all'interno di una casa del 1400 E' vicino a Siena, Firenze, San Gimignano, Volterra, ed alla zona del Chianti. Adatto a chi ama la campagna, ma vuole i vantaggi offerti da un Paese con tutti i servizi: negozi,ristoranti,bar,posta,banca,farmacia,chiesa,uff.turistico, museo. Vivi l'esperienza estiva di un paese che alterna la sua quiete a momenti animati da feste,mercatini,musiche e la tradizione del Palio (nella 2^ domenica di luglio).

Top guest favorite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 180 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 221 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favorite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 52 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Guest favorite
Cottage in Colle di Val d'Elsa
4.82 out of 5 average rating, 91 reviews

Rustico Toscano con piscina

Rustico con affaccia su tipica aia senese. E' al piano terra ed è composto da soggiorno cucina, un bagno e camera da letto con vista sul verde delle colline toscane. Ha un vasto giardino e piscina. Il Cottage è a uso esclusivo. La zona è molto tranquilla e ideale per vacanze in tutto relax. Ci troviamo nel mezzo a due significative città come Siena e Firenze, ma se volete scoprire borghi tipici a pochi km San Gimignano, Volterra, Monteriggioni.

Guest favorite
A rustic stone building features a charming entrance adorned with blooming flowers and lush greenery. The structure showcases traditional architecture with arched doorways and a tiled roof, set against a clear blue sky and surrounded by serene natural beauty.
Vacation home in Casole d'Elsa (SI)
4.92 out of 5 average rating, 225 reviews

Charming farmhouse with garden, views & pool

Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

Popular amenities for Casole d'Elsa vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Casole d'Elsa