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Holiday rentals with a pool in Guardistallo

Find and book unique homes with a pool on Airbnb

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 $102 NZD per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Guardistallo holiday 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

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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Guest favourite
Bungalow in Riparbella
4.93 out of 5 average rating, 41 reviews

Superior Lodge with 2 bedrooms and outdoor tub

An open air holiday in a comfortable solution: first bedroom with 1 bunk bed and a single bed, and a second one with a double bed; bathroom with shower, hairdryer, linen and courtesy kit. Living room with equipped kitchenette, small fridge and veranda. Our tents are located in a panoramic position, and is possible to enjoy the pools in our Resort - seasonal opening. Easily accessible by car, with a big and free of cost parking; outdoor tub for exclusive use, air conditioning, TV and free wi-fi. 

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Superhost
A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.
Home in Galluzzo
4.88 out of 5 average rating, 817 reviews

TREEhouse / casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.

LocationValueSleep quality

Guest favourite
Home in Montescudaio
4.96 out of 5 average rating, 131 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

ValueFamilyKitchen

Guest favourite
Cottage in Castellina in Chianti
4.97 out of 5 average rating, 112 reviews

Cappero Cottage - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

LocationValueWi-Fi

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.
Condo in Noce
5 out of 5 average rating, 343 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option 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 and vineyards with unique sunsets.

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Top Guest favourite
Home in Massa Marittima
5 out of 5 average rating, 70 reviews

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

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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, 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.

ValueFamilyAccuracy

Superhost
A spacious swimming pool is surrounded by lounge chairs and umbrellas, providing ample shade. Guests are seen enjoying the water, while the villa is visible in the background, set among tall trees and greenery under a clear blue sky.
Condo in Guardistallo
4.86 out of 5 average rating, 21 reviews

Two-room apartment with swimming pools and garden

Residence Villa Elena is a charming antique villa featuring annexes, thoughtfully subdivided into spacious apartments. Nestled on a hill, it offers stunning views of the countryside and the sea. The property boasts a beautifully maintained garden with furniture, parking facilities, two swimming pools, and a variety of amenities including bowls, ping-pong, children's play areas, a barbecue, and free Wi-Fi. Perfect for a relaxing and enjoyable stay amidst scenic surroundings.

FamilyLocationKitchen

Top Guest favourite
A spacious outdoor pool surrounded by deck chairs offers a serene view of the countryside. Thatched umbrellas provide shade, while the warm hues of sunset illuminate the rustic buildings in the background, emphasizing the tranquility of the setting.
Apartment in Santa Luce
4.93 out of 5 average rating, 59 reviews

Michelangelo apt ~ wild Tuscany Hills ~ Le Fraine

Take a break in the wild Tuscan hills, just 15 km from the sea. Agriturismo Le Fraine offers its guests 4 apartments and a large park with a pool overlooking the vineyards. The Michelangelo apartment is the perfect solution for a holiday to enjoy with your loved ones. It features two bedrooms (1 double bed - 2 single beds), a bathroom with a shower, a living room with a kitchen, and a sofa bed. From the private veranda, let your gaze wander over the hills and vineyards.

LocationFamilyIndoor spaces

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 102 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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Top Guest favourite
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
4.96 out of 5 average rating, 140 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.

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Guest favourite
The eco-friendly swimming pool reflects the rustic cottage and surrounding greenery under a clear blue sky. Smooth pebbles line the shallow area of the pool, creating a natural aesthetic. Tall cypress trees and a vibrant umbrella are visible, integrating seamlessly with the tranquil landscape.
Apartment in Guardistallo
5 out of 5 average rating, 15 reviews

Ai Massi Annamaria Farmhouse (three-room apartment 57sqm)

Apartment (three-room apartment of 57 sqm, sleeps 4) with sea view, located on the SECOND FLOOR of the farmhouse, entrance on the west side. It has a kitchen (equipped with a fridge, dishwasher, induction stove, microwave, kettle, toaster, immersion blender and Moka coffee maker), a living room (TV and Wi-Fi), two bedrooms with double bed and bathroom. The property has an eco-friendly swimming pool and overlooks the Etruscan Coast countryside.

ValueFamilyBathroom

Popular amenities for Guardistallo rentals with a pool

When is the best time to visit Guardistallo?

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Avg. price$362 NZD$304 NZD$270 NZD$275 NZD$262 NZD$268 NZD$321 NZD$380 NZD$263 NZD$285 NZD$297 NZD$362 NZD
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