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Holiday rentals with a pool in Asciano

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Asciano

  • Total holiday rentals

    Explore 500 holiday rentals in Asciano

  • Nightly prices starting at

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

  • Verified guest reviews

    Over 7,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    330 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    460 of Asciano holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Asciano rentals

  • 4.8 Average rating

    Asciano stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated rentals with a pool in Asciano

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

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Top guest favourite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Apartment in Asciano
4.92 out of 5 average rating, 179 reviews

Loggiato 3 apartment in Tuscany near Siena

The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

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, 321 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.

Top guest favourite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Holiday home in Chianciano Terme
5 out of 5 average rating, 116 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 124 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
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 215 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favourite
Home in Asciano
5 out of 5 average rating, 13 reviews

Sosta Eroica • Panoramic View & Quiet Pool Retreat

A pochi minuti da Siena, nel cuore autentico della Toscana, un luogo di pace relax e silenzio . vivi un soggiorno da sogno tra le Crete Senesi , Chianti, Val d’Orcia, Montalcino e Montepulciano. La casa è immersa in un paesaggio iconico di colline, cipressi e tramonti mozzafiato. Perfetta per coppie, famiglie e amanti della natura. Prenota e scopri esperienze uniche: degustazioni, tour e attività per vivere la Toscana come un local e a fine giornata rilassati nella nostra stupenda piscina .

Guest favourite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.96 out of 5 average rating, 70 reviews

Family Forest - Pool in the Crete Senesi

Relax with the whole family in our hideaway in Palazzo Monaci in the heart of the Crete Senesi! Our apartment is located in a residence with a swimming pool and breathtaking views, ideal 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 local wines, and immerse yourself in the culture and history of this fascinating region.

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 in Castellina in Chianti
4.98 out of 5 average rating, 129 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.

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 in Greve in Chianti
4.99 out of 5 average rating, 458 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
A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.
Loft in Siena
4.95 out of 5 average rating, 246 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Top guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 261 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Top guest favourite
A rustic terrace features a wooden table and chairs, offering panoramic views of rolling hills and lush greenery. Stone walls support a traditional wooden beam ceiling, while elements like a decorative bell and a sheep silhouette add character to the natural surroundings.
Farm stay in Pari
4.98 out of 5 average rating, 286 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool( open around the 10th of May) We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Popular amenities for Asciano rentals with a pool

When is the best time to visit Asciano?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$197 SGD$226 SGD$199 SGD$260 SGD$246 SGD$266 SGD$313 SGD$308 SGD$270 SGD$250 SGD$243 SGD$269 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Destinations to explore

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