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Holiday rentals with a pool in Poggibonsi

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Poggibonsi

  • Total holiday rentals

    Explore 20 holiday rentals in Poggibonsi

  • Nightly prices starting at

    Poggibonsi holiday rentals start at £67 per night before taxes and fees

  • Verified guest reviews

    Over 640 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Poggibonsi holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Poggibonsi rentals

  • 4.7 Average rating

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

Top-rated rentals with a pool in Poggibonsi

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

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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.
Apartment
5 out of 5 average rating, 340 reviews

Podere Vergianoni nestled in Chianti with a pool

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 a shuttle service and exclusive experiences tailored to your needs. 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'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

Guest favourite
Home
4.96 out of 5 average rating, 134 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
Home
4.91 out of 5 average rating, 195 reviews

La Casa di Nada - Suite

From every window of the house, beautiful views open onto the rolling Tuscan hills, a constant delight throughout the stay. The home is bright and welcoming, with comfortable bedrooms each featuring a private bathroom, a living room with a fireplace, and a fully equipped kitchen, the true heart of the home. For those who wish, it is possible—upon request—to enjoy a simple and authentic moment of cooking together, just like in a family home. A peaceful retreat in the heart of Chianti.

Top guest favourite
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
4.98 out of 5 average rating, 211 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa
4.99 out of 5 average rating, 137 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favourite
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
4.98 out of 5 average rating, 131 reviews

Private Chianti Cottage, Garden & Vineyard Views

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.

Guest favourite
Home
4.91 out of 5 average rating, 120 reviews

SuiteLouise.pool, Hot Tub,homeGym & private Garden

SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle
4.99 out of 5 average rating, 222 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favourite
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
5 out of 5 average rating, 133 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 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 aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Flat
4.92 out of 5 average rating, 381 reviews

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

Top guest favourite
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
4.96 out of 5 average rating, 202 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.

Popular amenities for Poggibonsi rentals with a pool

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Poggibonsi
  6. Rentals with pools