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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

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

4.97 out of 5 average rating, 182 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite

The spacious living area features a modern gray sectional sofa positioned in front of a sleek kitchen. A dining table with black chairs is set nearby, with large windows allowing natural light to illuminate the open space and providing views of the surrounding hills.

Apartment in Pievescola

4.99 out of 5 average rating, 117 reviews

Tuscan View 360: 3 bedr, 2 baths, free parking

Elegante e moderno appartamento situato nel borgo di Pievescola, tra Siena e Firenze, vicino a Monteriggioni e Parco Fluviale. A pochi passi dal ristorante, mini market, panificio, pasticceria, farmacia e banca. Ad uso esclusivo, raggiunto con scale al piano primo, si divide in: • 3 Camere da letto con materassi memory • 2 Bagni con doccia a cascata • Finestre con vista a 360 gradi sui colli • Soggiorno, cucina professionale e zona pranzo • Lavanderia interna con lavatrice e asciugatrice

Top guest favorite

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

4.96 out of 5 average rating, 252 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

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

4.99 out of 5 average rating, 188 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 lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.

Home in Castellina in Chianti

4.98 out of 5 average rating, 117 reviews

StageROOM03 -Chianti Idillic Country living

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 165 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

A spacious living area features a large window with elegant curtains, allowing natural light to illuminate the room. A comfortable sofa adorned with a cozy blanket is positioned facing a wooden coffee table, while a television and decorative elements add to the ambiance.

Condo in San Gimignano

4.94 out of 5 average rating, 124 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Top guest favorite

A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.

4.95 out of 5 average rating, 240 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Top guest favorite

The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.

Farm stay in Simignano

4.91 out of 5 average rating, 233 reviews

Casa al Gianni - Fico

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favorite

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 in Greve in Chianti

4.99 out of 5 average rating, 410 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Top guest favorite

The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.

Farm stay in Pisa

4.99 out of 5 average rating, 304 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.

Castle in Barberino Tavarnelle

4.88 out of 5 average rating, 113 reviews

Suite in Castle of Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

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Popular amenities for Casole d'Elsa vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Casole d'Elsa

Top guest favorite

A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.

Cottage in San Gimignano

4.97 out of 5 average rating, 74 reviews

Romantic House in Tuscany with jacuzzi

Top guest favorite

An outdoor space features a clear blue swimming pool surrounded by neatly trimmed grass and greenery. Sun loungers can be seen near the pool, with a stone pathway leading to nearby structures and trees dotting the background, creating a serene landscape.

Apartment in Colle di Val d'Elsa

5 out of 5 average rating, 6 reviews

La Loggetta, authentic Tuscany

Top guest favorite

A modern swimming pool is surrounded by a spacious wooden deck, lined with lounge chairs, offering expansive views of the rolling hills and olive groves. A large tree provides shade next to the pool, creating a serene outdoor space for relaxation.

Farm stay in Lastra a Signa

5 out of 5 average rating, 65 reviews

Authentic Farmhouse Apartment

Top guest favorite

The exterior of the two-story apartment is shown, featuring a staircase leading to the entrance. A stone pathway runs through a lush garden, adorned with potted plants. The building is complemented by a natural stone feature in the foreground, creating a welcoming entry space.

Townhouse in Quartaia

5 out of 5 average rating, 52 reviews

Casa Lida [Giardino+Parcheggio]

A private swimming pool is surrounded by a manicured lawn, featuring two lounge chairs with decorative pillows. A gazebo is visible in the background, offering a shaded area. Warm lights illuminate the garden and the villa, creating an inviting evening ambiance.

Villa in Capannori

4.97 out of 5 average rating, 33 reviews

Luxury Tuscany Villa on the hill with private pool

Top guest favorite

A sunlit veranda features ornate wooden ceiling details and floral-patterned seating. Potted plants create a lush atmosphere, while large windows offer views of the outside. A dining area with a table and chairs is visible, framed by elegant arched doors that open to the terrace.

Apartment in Centro Storico

5 out of 5 average rating, 35 reviews

Loggia in the Santo Spirito district

Top guest favorite

A tranquil terrace is surrounded by vibrant greenery, featuring a wooden table set for dining. Soft sunlight bathes the area, casting gentle shadows. The expansive view showcases rolling hills and distant mountains, creating a serene backdrop for outdoor relaxation.

Home in Pontassieve

4.97 out of 5 average rating, 91 reviews

The charming cottage in Tuscany with breathtaking views

Top guest favorite

A rustic stone building is set against a backdrop of rolling green hills and olive trees. A shaded pergola is visible in the foreground, offering a space to relax and enjoy the scenic views of the Tuscan countryside.

Farm stay in Radicondoli

5 out of 5 average rating, 16 reviews

The pomegranate, Podere il Giglio

Quick stats about vacation rentals in Casole d'Elsa

Total rentals
10 properties
Nightly prices starting at
R1,412 ZAR before taxes and fees
Total number of reviews
350 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool

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 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!
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.

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