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Vacation 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 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, 305 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.

Guest favorite
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 favorite
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.

Guest favorite
An inviting outdoor space is presented, featuring a clear pool reflecting the evening sky. Comfortable lounge chairs are arranged nearby on the well-maintained lawn, surrounded by potted plants. The scenic hillside view in the background adds to the serene atmosphere.
Condo in Morrona
4.96 out of 5 average rating, 142 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

My husband and I fell in love at first sight with this beautiful place. So we have moved here our whole life. Ideally located on the hill of Morrona,this landscape affords unique views over the hills near Pisa,put us in direct contact with a calm nature and gives us a wonderful spectacle of the fascinating and surprising course of seasons. The location is enhanced by the swimming pool with hydromassage,for those seeking a moment that will remain on their skin and in their hearts for a long time

Guest favorite
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 favorite
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.
Vacation home in San Gimignano
4.96 out of 5 average rating, 50 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 favorite
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)

Top guest favorite
A refreshing pool area features a thatched umbrella providing shade over several sun loungers. The calm water reflects the surrounding Tuscan landscape, which includes rolling hills and a clear blue sky with scattered clouds.
Apartment in Santa Luce
4.96 out of 5 average rating, 75 reviews

Modigliani apt in the wild Tuscany Hills~Le Fraine

Nestled in the heart of the wild Tuscan hills, at 15 km from the sea, lies Le Fraine. A working farm resort, surrounded by vineyards and olive groves with a privileged view of the Santa Luce natural lake reserve. Where Nature prevails and our guests are treated like friends. Experience a memorable stay immersed in nature, with all the comforts and privacy you could wish for.

Top guest favorite
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.

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, 316 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
A spacious bedroom is illuminated by natural light filtering through a Velux window in the angled ceiling. The room features a comfortable bed with a light-colored headboard, accompanied by nightstands with bedside lamps. A wooden wardrobe and a colorful area rug add warmth to the space.
Apartment in Riparbella
5 out of 5 average rating, 45 reviews

Cancellaia - lovely attic apartment in farmhouse

Take it easy in this attic apartment on the second floor of the farmhouse of 1745, in the farmhouse of our winery. A cozy, quiet, and relaxing space, equipped with a large kitchen, small living room with table and TV, large double bedroom and a nice bathroom with shower.

Top guest favorite
The suite features a spacious bed positioned against a decorative wall, complemented by a free-standing bathtub nearby. A window allows natural light to fill the room, showcasing the charming stone wall that adds character to the space.
Farm stay in Lastra a Signa
4.99 out of 5 average rating, 100 reviews

Charming Farmhouse Suite

Tenuta Barosi, Isabella Suite - Experience the charm of Tenuta Barosi, a newly renovated agriturismo in 2024. Perched on a hilltop amidst olive groves, this serene retreat in Malmantile, a medieval village near Florence, offers stunning views and modern comforts.

Popular amenities for Guardistallo rentals with a pool

When is the best time to visit Guardistallo?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,265 GYDG$32,999 GYDG$34,252 GYDG$30,284 GYDG$28,195 GYDG$32,999 GYDG$39,474 GYDG$46,783 GYDG$32,372 GYDG$35,088 GYDG$36,550 GYDG$44,486 GYD
Avg. temp7°C8°C10°C13°C17°C21°C24°C24°C21°C17°C12°C8°C

Quick stats about vacation rentals with a pool in Guardistallo

  • Total vacation rentals

    Explore 130 vacation rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo vacation rentals start at G$12,531 GYD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Guardistallo vacation rentals include wi-fi 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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