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Holiday rentals 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 £52 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    10 of Casole d'Elsa holiday rentals include wifi 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
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.
Flat
5 out of 5 average rating, 37 reviews

Holiday House "Anna" - the MUSICIAN for 4-5 persons

"the MUSICIAN" IS located IN the historic center, inside a house from 1400 IS near Siena, Florence, San Gimignano, Volterra, and the Chianti area. Suitable for those who love the countryside, but want the advantages offered by a country with all the services: shops,restaurants,bars,post office,bank,pharmacy,church, tourist office, museum. Live the summer experience of a country that alternates its tranquility with moments animated by parties,markets,music and the tradition of the Palio (on the 2nd Sunday of July).

Top guest favourite
A welcoming entrance features a stone wall adorned with vibrant flower pots. A spacious patio leads to the home, complemented by a wooden bench and a picturesque natural landscape in the background, showcasing rolling hills under a clear sky.
Home
4.99 out of 5 average rating, 107 reviews

Casa Panorama

Welcome to Casa Panorama! A cozy apartment situated in the wonderful Tuscan countryside just a stone's throw away from the medieval town of Casole d'Elsa.Casa Panorama is in between some of the most beautiful locations such as Siena,Monteriggioni,Florence,San Gimignan,Volterra and many other hidden hilltop Tuscan jewels.Our house is situated less than 1 km from the center of the very romantic town of Casole d'Elsa where there are restaurants and much to see as far as culture and art is concerned

Guest favourite
Cottage
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

Guest favourite
Apartment
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.

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.
Flat
4.97 out of 5 average rating, 32 reviews

Mirella apartment in the historic center

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 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
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.

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.
Apartment
4.97 out of 5 average rating, 112 reviews

Manuela apartment with pool in farmhouse

You will be staying in an apartment located on the first floor, with a separate entrance and accessed by climbing 17 steps. It consists of a kitchen, two bedrooms (one double and one with 2 single beds), a bathroom with a shower and mosquito nets on the windows. Small balcony shared with the GIRASOLI apartment. IT IS MANDATORY TO PAY THE TOURIST TAX AT CHECK-IN: €1 per person for the first 5 days. Heating is allowed from 1 November to 15 April (regional law) at €20.00 per day

Top guest favourite
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.
Apartment
5 out of 5 average rating, 56 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.”

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay
4.92 out of 5 average rating, 276 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 475 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.
Flat
4.99 out of 5 average rating, 85 reviews

Herons Superior Apartment - Splendid view!

Goditi una vacanza all'insegna dello stile in questo spazio nel centro di San Gimignano. Finemente arredato e con una vista spettacolare sulle colline toscane, Herons Superior Apartment è pronto a ospitarti insieme alle persone che ami. ___________________________________________________ Tassa di soggiorno da pagare sul posto secondo il seguente calcolo: 2,5€ X numero di ospiti sopra gli 11 anni X numero di notti (si pagano al massimo 5 notti).

Guest favourite
A bright and functional kitchen area is showcased, featuring wooden beams overhead and light-colored cabinetry. A dining table is set with dishes and glasses, complemented by a vintage-style blue refrigerator. Essential appliances and a stove are included, highlighting a comfortable cooking space.
Flat
4.92 out of 5 average rating, 26 reviews

Chianti, apartment in a Villa

Elegant apartment in a historic villa in the heart of Chianti, carefully furnished to offer comfort and functionality to travelers from all over the world. The strategic location allows you to explore the wonders of Tuscany: San Gimignano (25 min), Volterra (30 min), Monteriggioni (35 min), Siena (40 min), and Florence (1 hour). Perfect for those who want relaxation, culture, breathtaking landscapes and fantastic food and wine tours.

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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