
Vacation rentals with a pool in Asciano
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Asciano

Total vacation rentals
Explore 500 vacation rentals in Asciano

Nightly prices starting at
Asciano vacation rentals start at G$12,531 GYD per night before taxes and fees

Verified guest reviews
Over 7,820 verified reviews to help you choose

Family-friendly vacation rentals
330 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
460 of Asciano vacation 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.

Podere Vergianoni immerso nelChianti con piscina
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.

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.

Loggia 1 in farmhouse with shared pool
Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

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.

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.

Vineyards Paradise
Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

Stone House with Exclusive Pool Codilungo in Chianti
Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

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.

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

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.

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.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
Popular amenities for Asciano rentals with a pool
House rentals with a pool

Cozy country house Podere Scorno with pool

Infinity pool in Chianti area

Ancient Barn in Chianti with Pool

Antico Borgo Ripostena – n. 5 Garage

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Luxury Villa with a fantastic view
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Ginestra: Private Pool Overlooking Florence
Home rentals with a private pool

Wp Relais Borgo Vignalunga

Villa Pergo is an ancient charming country villa

Historic home with exclusive pool

Charming villa in the Chianti hills

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 | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$32,372 GYD | G$36,966 GYD | G$32,581 GYD | G$42,605 GYD | G$40,308 GYD | G$43,650 GYD | G$51,377 GYD | G$50,542 GYD | G$44,276 GYD | G$40,935 GYD | G$39,890 GYD | G$44,067 GYD |
| 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
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Venice Vacation rentals
- Florence Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Bonifacio Vacation rentals
- Rentals with a washer and dryer Asciano
- Condo rentals Asciano
- Family-friendly rentals Asciano
- Rentals with outdoor seating Asciano
- Rentals with a fireplace Asciano
- Farmstay rentals Asciano
- Rentals with breakfast Asciano
- Luxury rentals Asciano
- Vacation home rentals Asciano
- Rentals with a fire pit Asciano
- Rentals with a patio Asciano
- Apartment rentals Asciano
- Rentals with lake access Asciano
- Pet-friendly rentals Asciano
- Smoking-friendly rentals Asciano
- Rentals with an EV charger Asciano
- House rentals Asciano
- Rentals with a hot tub Asciano
- Villa rentals Asciano
- Bed and breakfasts Asciano
- Fitness-friendly rentals Asciano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Lake Bolsena
- Basilica of Santa Maria Novella
- Strozzi Palace
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Mercato Centrale
- Basilica Di San Miniato A Monte
- Eremo Di Camaldoli
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Palazzo Vecchio
- Boboli's Garden
- Avignonesi Winery Fattoria Le Capezzine
- Things to do Asciano
- Things to do Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Art and culture Siena
- Tours Siena
- Food and drink Siena
- Sports activities Siena
- Things to do Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Entertainment Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Wellness Italy
- Entertainment Italy
- Nature and outdoors Italy
- Sports activities Italy
- Tours Italy
- Sightseeing Italy
- Art and culture Italy






