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Vacation rentals with a pool in Montaione

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Montaione

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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, 293 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favorite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 204 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Guest favorite
A dining table is set under the shade of lush trees, featuring a bottle of wine and glasses. The surrounding garden is filled with tall cypress trees and vibrant greenery, creating a serene atmosphere for outdoor dining.
Farm stay in San Casciano In Val di Pesa
4.78 out of 5 average rating, 163 reviews

Sperone: two floors apartment with pool

Just a few km from Florence and surrounded by vineyards and olive groves of the Principe Corsini estate, this is the ideal place for a classic Tuscan-style holiday in the heart of Chianti Classico. The private garden, which also provides access to the pool at Villa Le Corti, is ideal for relaxing and peaceful al fresco dining. The pool, open from June to September, has a breathtaking view of Tuscan rolling hills. The property includes a parking area reached from the entrance gate.

Top guest favorite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top guest favorite
A spacious living area is furnished with a dining table and four chairs, complemented by a cozy sofa. Large windows offer views of the surrounding landscape, while subtle natural light filters through textured shades. A television is mounted on the wall, with a glimpse of an elegant bathroom in the background.
Loft in Scandicci
4.98 out of 5 average rating, 127 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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, 433 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 favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 124 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favorite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano
4.96 out of 5 average rating, 190 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Guest favorite
A spacious living area features a traditional stone fireplace with a wooden beam mantle. Decorative tiles line the floor, and light enters through two windows on either side. A potted plant adds a touch of greenery, while an elegant television is positioned nearby.
Home in Barberino Tavarnelle
4.9 out of 5 average rating, 171 reviews

La Casa di Nada - Suite

Every window of my house opens onto wonderful views of the Tuscan hills, an enchantment that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room, I have a beautiful fireplace all for you. A practical, complete laundry room in this refuge in the Heart of Chianti

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, 313 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.

Top guest favorite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay in Palaia
4.98 out of 5 average rating, 179 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded 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.

Top guest favorite
A serene pool area is featured, surrounded by well-maintained greenery. Several lounge chairs are positioned along the pool's edge, inviting relaxation. The sky is clear and blue, complementing the tranquil setting of the property.
Villa in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 164 reviews

Podere Guidi

Apartment in a panoramic villa between Florence and Siena in the heart of Chianti in a charming village. The swimming pool is open from May 1st to September 30th, from 9 a.m. to 1 p.m. with exclusive use for guests during this time. For different needs, ask the host.

Popular amenities for Montaione rentals with a pool

Quick stats about vacation rentals with a pool in Montaione

  • Total vacation rentals

    Explore 20 vacation rentals in Montaione

  • Nightly prices starting at

    Montaione vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 140 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Montaione vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montaione rentals

  • 4.7 Average rating

    Montaione stays receive an average rating of 4.7 out of 5 from guests

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