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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
Flat
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
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
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
An inviting kitchen area features a glass dining table surrounded by blue chairs. Stone walls complement modern cabinetry and appliances, illuminated by a contemporary circular light fixture. A warm ambiance is created by the rustic elements and soft lighting throughout the space.
Flat
4.96 out of 5 average rating, 23 reviews

Il Frantoio (Hot Tub + Fireplace)

Romantic ✨ retreat in the heart of Tuscany — perfect in every season 🍂 Welcome to Palazzo Riccardi, a historic building in the charming village of Rivalto, where Tuscan authenticity meets modern design. Let yourself be won over by the wood-burning fireplace, the bathroom with a hot tub and a warm and enveloping atmosphere. Ideal for couples looking for relaxation and charm, this apartment is a perfect nest in every season but it is in autumn and winter that it becomes truly magical 💫

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

In the Tuscan green, Podere I Places with swimming pool Ap1

In an ancient farmhouse from the 1800s, a lovely apartment surrounded by greenery in the Tuscan countryside, on a hill with beautiful sea views. It has 3 double rooms with private bathroom, equipped kitchen, dining room and outdoor area ideal for outdoor dinners and relaxation. Seasonal 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.

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, 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
A panoramic view captures a charming estate set against rolling hills and a clear blue sky. The property features a saltwater pool surrounded by lush greenery. The landscape is dotted with cypress trees and fields in varied shades of green and brown.
Guest suite
5 out of 5 average rating, 37 reviews

Oliva Suite - La Vitaverde Agriturismo

Adults only - minimum age 18 years | Our suites are self-catering apartments, and we do not offer traditional hotel services! Agriturismo La Vitaverde is more than just a place to stay. Nestled among gentle hills and fragrant olive groves, our lovingly restored estate combines tradition and comfort in perfect harmony. Here, you can escape the hustle and bustle of everyday life, enjoy the rustic charm of the region, and immerse yourself in the relaxed lifestyle of Tuscany.

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
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 IT050012C2LZ3CHRNQ)

Guest favourite
Flat
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.

Guest favourite
Home in Lajatico
5 out of 5 average rating, 6 reviews

Margherita: Tuscany views, Pool & Walk to Village

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

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
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 favourite
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
4.99 out of 5 average rating, 314 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.

Guest favourite
The living area features a cozy seating arrangement with a yellow sofa and a white armchair. A wooden dining table with chairs is positioned near an arched window, providing a view of the outdoors. Exposed wooden beams and terracotta tiles complement the rustic design.
Flat
5 out of 5 average rating, 18 reviews

Gorgona - cozy apartment in farmhouse

Relax in this quiet and cozy accommodation in the agriturismo of our wine estate. Thanks to the antique details of wood and brick and the furnishings in traditional style combined with modern comforts and its warm atmosphere, it will fill your days of freedom and relaxation.

Popular amenities for Guardistallo rentals with a pool

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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 £45 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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