
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 480 holiday rentals in Asciano

Nightly prices starting at
Asciano holiday rentals start at €52 per night before taxes and fees

Verified guest reviews
Over 8,050 verified reviews to help you choose

Family-friendly holiday rentals
310 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
450 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.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
4.99 out of 5 average rating, 113 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.
4.93 out of 5 average rating, 201 reviews
Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
4.9 out of 5 average rating, 240 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.
4.96 out of 5 average rating, 138 reviews
House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.
4.96 out of 5 average rating, 122 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
4.99 out of 5 average rating, 113 reviews
San Giovanni in Poggio, Villa Meriggio 95 sqm
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.
4.98 out of 5 average rating, 128 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.
4.98 out of 5 average rating, 105 reviews
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.
4.99 out of 5 average rating, 431 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
4.89 out of 5 average rating, 307 reviews
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.
4.86 out of 5 average rating, 122 reviews
Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
4.99 out of 5 average rating, 117 reviewsPopular amenities for Asciano rentals with a pool
House rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
4.92 out of 5 average rating, 172 reviews
La Lisa: country house surrounded by fields
4.94 out of 5 average rating, 135 reviews
Cercis - La Palmierina
4.96 out of 5 average rating, 144 reviews
Cottage surrounded by nature
4.99 out of 5 average rating, 110 reviews
Villa Lolù with private heated swimming-pool
4.97 out of 5 average rating, 159 reviews
Borgo Ripostena – No. 8 Casa Vecchia
4.95 out of 5 average rating, 200 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 136 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 122 reviewsApartment rentals with a pool

Historic 17th-century farmhouse in Chianti, Tuscany
5.0 out of 5 average rating, 218 reviews
La Casetta
4.93 out of 5 average rating, 194 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 280 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 300 reviews
Poggiolieto Suite - on hills 10' from city center
4.83 out of 5 average rating, 227 reviews
Cozy home in countryside with tennis and pool
4.54 out of 5 average rating, 90 reviews
PODERE SCURCOLI FARMHOUSE
5.0 out of 5 average rating, 11 reviews
Apartment in ancient house + pool and terrace
4.94 out of 5 average rating, 18 reviewsHome rentals with a private pool
Wp Relais Villa Vignalunga
4.93 out of 5 average rating, 116 reviews
Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 216 reviews
TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 820 reviews
Explore nature in the center of Vigneti Chianti
4.97 out of 5 average rating, 264 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 121 reviews
Magnificent Tuscan Villa, amazing interiors & view
5.0 out of 5 average rating, 16 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Podere Molinaccio - Luxury Tuscan-style Eco Villa
4.93 out of 5 average rating, 27 reviewsWhen is the best time to visit Asciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €176 | €178 | €168 | €171 | €178 | €180 | €212 | €209 | €183 | €169 | €165 | €182 |
| 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 pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Stazione Santa Maria Novella
- Parco Regionale Della Maremma
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Things to do Asciano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Tastings Tuscany
- Workouts Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Food tours Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Landmarks Italy







