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Holiday rentals with a pool in Guardistallo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Guardistallo

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 in Noce
5 out of 5 average rating, 303 reviews

Podere Vergianoni nestled in Chianti with a pool

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.

Guest favourite
Farm stay in Casale Marittimo
4.86 out of 5 average rating, 7 reviews

In the Tuscan countryside, Podere I Luoghi with swimming pool Ap1

In an old 19th-century farm, a lovely apartment surrounded by the greenery of the Tuscan countryside, on a hill with a beautiful sea view. It has 3 double bedrooms with a private bathroom, an equipped kitchen, a dining room and an outdoor area ideal for outdoor dining and relaxation. Seasonal swimming pool from June to September. Just 12 km from the sea, perfect for visiting villages such as Bolgheri, Castagneto Carducci, Montescudaio and Volterra, among hills, vineyards and authentic flavors.

Guest favourite
A clear, tranquil salt-water infinity pool reflects the bright blue sky and scattered clouds. Lush greenery, including tall cypress and evergreen trees, frames the pool area, enhancing the serene outdoor environment.
Loft in Rosignano Marittimo
4.95 out of 5 average rating, 112 reviews

Il Cubetto -Sea Studio: sense of peace and freedom

Our little place, Il Cubetto, inaugurated with the 2020 season, stands in full Tuscan country and is particularly distinctive because of its absolute exclusivity: only two studio apartments within our 7000 sqm of garden planted with many fruit trees, with great attention to any detail. Our guests, a maximum of two per studio apartment, have the use of a salt-water infinity swimming pool overlooking the valley. Depending on the car they drive, they can park next to the cottage or beside the road.

Top guest favourite
Flat in Caminino
4.91 out of 5 average rating, 184 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Guest favourite
The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.
Home in Volterra
4.93 out of 5 average rating, 193 reviews

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

Guest favourite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 123 reviews

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

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 in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 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
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Holiday home in San Gimignano
4.96 out of 5 average rating, 48 reviews

Peaceful tuscan house with pool in Tuscany

An oasis of peace located in the heart of Tuscany and on the wine roads! -A strategic area between Certaldo, San Gimignano, Siena and Florence. -Casa Valentina is hidden in a grove where you will enjoy fresh air, a stream with the chirping of birds and a wonderful swimming pool where you can enjoy our breathtaking views -A newly renovated house that meets the historicity of the property, the comfort and the contemporaneity that makes it unique in its style.

Guest favourite
The tranquil salt-water pool reflects the colors of the sunset, creating a serene atmosphere. Lush landscapes surround the pool area, with silhouettes of trees and hills visible in the background. A patio set can be seen nearby, suggesting a space for relaxation.
Home in Chianni
5 out of 5 average rating, 16 reviews

The Cottage to relax and enjoy

Detached country house – for exclusive use – in stone and glass from the 18th century; ideal for 4 people. The spacious wooden terrace at the house with a large dining table invites you to socialize. On the terrace by the saltwater pool (10m x 5m, depth 1.4m-2.4m), you can relax on the sun loungers and deckchairs. Large property with olive and fruit trees, completely self-sufficient accommodation thanks to photovoltaics. (CIN IT050012C29N4AT4OD)

Superhost
Flat in Castagneto Carducci
5 out of 5 average rating, 13 reviews

Podere Bagnoli: Acanto House

A blast from the past. This enchanting apartment, created from the original settlement of the farmhouse, still preserves the charm of the past intact. The large fireplace with the frescoed coat of arms is a real piece of history, which tells the story of the family that once lived here. The stylish floors, exposed beams and furniture create a warm and welcoming atmosphere. Everything contributes to making the environment unique and evocative.

Guest favourite
Flat in Santa Luce
4.93 out of 5 average rating, 56 reviews

Leonardo apt. in the wild Tuscany hills~ Le Fraine

Treat yourself to a holiday immersed in the Tuscan countryside, surrounded by vineyards and olive groves. The Leonardo apartment is located on the first floor of the farmhouse. It features a bedroom with a double bed, a bathroom with a shower, and a living room with a kitchen and a sofa bed. From the window, you can catch a glimpse of the old olive grove, and the first rays of sunlight will gently wake you to start your day in the best way.

Top guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Farm stay in Castagneto Carducci
4.99 out of 5 average rating, 114 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Popular amenities for Guardistallo rentals with a pool

When is the best time to visit Guardistallo?

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Avg. price$239 SGD$201 SGD$209 SGD$185 SGD$172 SGD$201 SGD$241 SGD$285 SGD$197 SGD$214 SGD$223 SGD$271 SGD
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Quick stats about holiday rentals with a pool in Guardistallo

  • Total holiday rentals

    Explore 130 holiday rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    110 of Guardistallo holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Guardistallo rentals

  • 4.6 Average rating

    Guardistallo stays receive an average rating of 4.6 out of 5 from guests

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