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Holiday houses in Casole d'Elsa

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Casole d'Elsa

  • Total holiday rentals

    Explore 10 holiday rentals in Casole d'Elsa

  • Nightly prices starting at

    Casole d'Elsa holiday rentals start at $101 AUD per night before taxes and fees

  • Verified guest reviews

    Over 390 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Casole d'Elsa holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Casole d'Elsa rentals

  • 5 Average rating

    Casole d'Elsa stays are highly rated by guests—averaging 5 out of 5!

Top-rated holiday rentals in Casole d'Elsa

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

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Top Guest favourite
Cottage in Casole d'Elsa
4.94 out of 5 average rating, 32 reviews

Whispering cypresses cottage. Stunning pool view.

✅ 45 m² entirely on ground floor with full,bright equipped kitchen ,1 double bedroom ,1 bedroom with 2 twin beds both with airco, 1 bathroom. Large patio with shade ideal for morning coffee and family meals ✅ Panoramic pool with glorious hill views ✅ 1 km easy walking to the medieval town Casole ,with cobblestone streets and delightful restaurants.A real hidden gem! ✅ Central location to visit the best Tuscany💖 Leccio Cottage is part of Monti 1824 farm,composed of 6 accommodations + pool

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Guest favourite
Condo in Casole d'Elsa
4.94 out of 5 average rating, 17 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.

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Top Guest favourite
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, 112 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

ValueFamilyQuiet

Top Guest favourite
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, 340 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.

LocationFamilyAccuracy

Top Guest favourite
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

LocationFamilyOutdoor spaces

Top Guest favourite
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).

FamilyLocationHospitality

Top Guest favourite
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, 181 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!

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Top Guest favourite
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, 223 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.

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Guest favourite
Castle in Tignano
5 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.

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Top Guest favourite
Home in Barberino Tavarnelle
5 out of 5 average rating, 75 reviews

Happy Stay in a Tuscany Home with Stunning Views

An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an samazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

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Top Guest favourite
Condo in Colle di Val d'Elsa
5 out of 5 average rating, 19 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

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Top Guest favourite
Dome in Volterra
4.98 out of 5 average rating, 120 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

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Popular amenities for Casole d'Elsa holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Casole d''Elsa?

    Casole d''Elsa has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Casole d''Elsa?

    Four-legged friends are welcome in Casole d''Elsa. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Casole d''Elsa?

    Yes! Work meets play with ease at over 10 vacation rentals in Casole d''Elsa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Casole d''Elsa vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Casole d''Elsa, available on Airbnb. Make a splash and soak up the sun in style!

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