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Holiday rentals in Montespertoli

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Montespertoli

  • Total holiday rentals

    Explore 30 holiday rentals in Montespertoli

  • Nightly prices starting at

    Montespertoli holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 1,630 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 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

    30 of Montespertoli holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montespertoli rentals

  • 4.9 Average rating

    Montespertoli stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Montespertoli

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

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Top guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment in Noce
5.0 out of 5 average rating, 218 reviews

Historic 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising exclusive services and experiences tailored to you. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you will find a saltwater swimming pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills and vineyards, with breathtaking sunsets.

Top guest favourite
A well-maintained garden features a green lawn surrounded by olive trees. Colorful flower pots with red blooms accent the space. A shaded seating area under a canopy provides a cozy spot for relaxation, with additional garden ornaments and a path leading through the landscape.
Cottage in Montespertoli
4.91 out of 5 average rating, 141 reviews

Casa del Sole in Chianti

Typical Tuscan country house in stone with fireplace, large garden, with parking. In the garden, there is a barbecue and wood-burning oven for pizza. The house is nestled among the vineyards and olive groves of Chianti Classico in a small country village. It is 4 km from San Casciano Val di Pesa, 20 km from Florence, 22 km from San Gimignano and 40 km from Siena. A1 Impruneta highway exit 8 km, SGC Fi-Siena 3 km. The house has three bedrooms, one of which is in the annex with bathroom and independent access.

Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 338 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top guest favourite
Home in Montespertoli
5.0 out of 5 average rating, 23 reviews

Villa la scuderia quiet luxury private garden pool

Once a 19th-century horse stable, this Tuscan home was discovered by my mother : a Dutch artist and traveller, she moved here in search of beauty, nature and light. She stayed for twenty years. My brother and my daughter grew up running barefoot on these ancient terracotta floors. Even today I still fall in love with the light that enters through the old arches and reflects into the house and the flower-filled private garden.its not an hotel is a lifetime experience, welcome to” La scuderia “.

Top guest favourite
The entrance features a sturdy door with a reflective surface, framed by a rustic stone wall and accented by a decorative lantern. A window with iron bars contains flower pots, contributing to the charming exterior of the villa.
Guest suite in Montespertoli
4.98 out of 5 average rating, 136 reviews

Villa i Lecci 1

At Villa i Lecci you will have an accommodation for exclusive use, surrounded by the beautiful Chianti landscape, just 1.8 km from the town center. The two double bedrooms, cozy and spacious, are connected by a corridor to the living room with fireplace and to the dining room with kitchen. Perfect for a relaxing pool vacation or a tour of Chianti and the main Tuscan cities, Florence, Siena, Pisa, San Gimignano and Volterra. Suitable for couples, families, and groups of friends.

Guest favourite
A dining area is illuminated by natural light pouring through an open window. A wooden table is set for four, surrounded by white chairs. Scenic hills are visible through the window, enhancing the inviting atmosphere of the space.
Flat in Montespertoli
4.92 out of 5 average rating, 146 reviews

La Chicchera, ground floor apt with panoramic view

La Chicchera is a recently renovated apartment with attention to detail in a very quiet street in the centre of Montespertoli, a small town in the heart of Chianti and a short distance from Florence and all the other cities of art in Tuscany. Mini-markets, bars, pharmacies, restaurants, shops, banks are within easy walking distance; bus stops are also within walking distance. We will be happy to welcome you and be part of your stay in Tuscany with tips and tricks!

Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favourite
A charming house is framed by lush greenery, with several trees dotting the manicured lawn. The exterior features warm tones, complemented by a covered porch area. Various plants provide a natural ambiance, enhancing the serene outdoor space.
Home in Montespertoli
4.84 out of 5 average rating, 148 reviews

I Limoni Apartment in Tuscany

In the Chianti hills between Florence Siena rich in history and evocative natural sceneries, the cradle of civilizations that have left an artistic and cultural heritage of unparalleled value, surrounded by unspoiled nature luxuriant vineyards cultivated as gardens, centuries-old olive groves, imposing cypresses, is the "VillaBassa" farm is located. easily accessible Florence 30 min Pisa 50 min Siena 50 min S.Gimignano 30 min Monteriggioni 45 min

Top guest favourite
A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.
Villa in Montespertoli
4.95 out of 5 average rating, 219 reviews

Farmhouse in Chianti

Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Top guest favourite
A panoramic view captures a hillside town featuring a historic tower, surrounded by lush greenery and rolling vineyards. The landscape displays a blend of trees, fields, and distant hills under a clear sky, showcasing the natural beauty of the Tuscan countryside.
Holiday home in Montespertoli
4.95 out of 5 average rating, 146 reviews

Chianti Panorama | House with 3 En-Suite Bathrooms

Immerse yourself in the authentic magic of Chianti 🍷 in our exclusive country home 🏡, boasting panoramic views over Montespertoli and its rolling hills . Strategically located just 1 km from the town center and main amenities 🛍️ like cafes ☕, restaurants 🍽️, and supermarkets 🛒, it is within easy reach of Florence , San Gimignano , Volterra and Siena . All the wonders of Tuscany will be just a charming day trip away!

Guest favourite
An aerial view captures a rustic countryside villa nestled within lush greenery and olive groves. The structure features a tiled roof and surrounded by trees, with a separate building visible nearby. The serene landscape enhances the sense of privacy and tranquility.
Home in Montespertoli
4.91 out of 5 average rating, 126 reviews

Costalmandorlo, a rustic home in the heart of Tuscany

Costalmandorlo is your peaceful corner in the center of Tuscany. A charming country cottage restored and furnished with care and with a style that combines ancient and modern. Here you can slow down and relax surrounded by the sounds of nature, admiring beautiful sunsets and having long breakfasts in the garden. A short distance between Florence, Siena and Pisa, it is an excellent base for touring Tuscany.

Guest favourite
A charming entrance features a stone facade with a wooden door framed by a decorative wrought-iron security grate. Steps lead to the door, flanked by a potted plant and shrubs, adding a touch of greenery to the welcoming entrance.
Home in Montespertoli
4.95 out of 5 average rating, 108 reviews

CASA DI CARLA spacious apartment in Chianti

Spacious and bright Tuscan-style apartment located in a characteristic village near Tavarnelle Val di Pesa. Quiet and peaceful, in the heart of the Chianti hills, in an excellent location for reaching Florence and other Tuscan cities of art. Private garden, with gazebo, sofas and barbecue, adjacent to the apartment. Public parking is available nearby.

Popular amenities for Montespertoli holiday rentals

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Montespertoli?

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

  • Are there vacation rentals with a dedicated workspace in Montespertoli?

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

  • Are there Montespertoli vacation rentals on Airbnb with pools?

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

  • Are there family-friendly apartment rentals in Montespertoli?

    Montespertoli has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Montespertoli?

    Experience the best of Montespertoli with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Montespertoli have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Montespertoli. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Montespertoli have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Montespertoli. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Montespertoli have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Montespertoli. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Montespertoli have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Montespertoli. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Montespertoli?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.