
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 $106 NZD per night before taxes and fees

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Over 7,820 verified reviews to help you choose

Family-friendly holiday rentals
330 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
460 of Asciano holiday rentals include Wi-Fi 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.

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.

Siena - apartment in the countryside near Siena
The Siena apartment for 5 people is located in the Santa Lucia farmhouse (DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is an apartment of about 100 square meters, located on the ground floor, consisting of three bedrooms (one double; one with two beds and one single), a large living room with fireplace, kitchen, two bathrooms with shower. Private outdoor gazebo with table and benches located in a private garden. AIR CONDITIONING in the rooms for a FEE according to consumption.

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.

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 .

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

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.

Casa Biancospino Crete Senesi | Podere Fossaccio
Casa Biancospino is an apartment with a private courtyard inside the Podere Fossaccio. Suitable for short and medium/long stays and is located in the heart of the Crete Senesi. The location is strategic for visiting the most interesting places in Tuscany. The green areas and a magnificent infinity pool overlooking the surrounding hills will be available to you and the other guests of the Podere. A warm and welcoming atmosphere where you can breathe the authentic Tuscan atmosphere.

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.

The Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Appaloosa - Apartment for couples and families
Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.
Popular amenities for Asciano rentals with a pool
House rentals with a pool

Italian Internal

Cercis - La Palmierina

Farmhouse on a winery

Private villa/swimming pool in Tuscany

Charming estate with views. A/C in the bedrooms

Relaxation and charm in the Chianti hills

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Nada Home
Condo rentals with a pool

Scenic Stilish Country

Lornano Winery Farm - Villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Farmhouse near Florence - Loggia

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Poggiolieto Suite - on hills 10' from city center

Il Fienile, 2 bedrooms with patio
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa
Historic villa x8 with exclusive pool

Agriturismo Henni panoramic pool sauna and jacuzzi

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Farmhouse , pool, 13 px. Lucca 10km
When is the best time to visit Asciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $359 NZD | $363 NZD | $344 NZD | $359 NZD | $340 NZD | $368 NZD | $434 NZD | $426 NZD | $374 NZD | $345 NZD | $337 NZD | $372 NZD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Bed and breakfasts Asciano
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- Rentals with lake access Asciano
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- Rentals with a hot tub Asciano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Parco Regionale Della Maremma
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Centro Storico Orvieto
- Cascate del Mulino
- Basilica of Santa Croce
- Things to do Asciano
- Things to do Siena
- Sports activities Siena
- Sightseeing Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
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