
Holiday rentals with a pool in Monticiano
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Monticiano
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

San Giovanni in Poggio, villa Meriggio 95mq
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.

StageROOM03 - Idyllic Chianti cottage near Siena
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.

La Villa Farmhouse - Chestnut, Pool & Garden
Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

Country house near Siena
The apartment is on the ground floor of a farmhouse of 1600, it is very cozy, the floors are in wood and the walls are painted in bright colors. The house consists of a large kitchen, a bedroom where there is also a sitting area with a comfortable sofa that can accommodate two people and a fireplace near the sofa. The house is surrounded by beautiful hills and woods. In front of the house there is a terrace where to eat, and a garden with deckchairs.

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

Tuscan countryside, peace and relaxation 10 minutes from Siena
Our accommodation is close to Siena, therefore to nightlife, the city center but also to the small airport of Ampugnano, parks, and public transport. You'll love our place for its light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our apartment is suitable for couples, solo adventurers, business travelers, families (with children) and furry friends (pets).

Old hayloft on the Chianti hills
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. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for Monticiano rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

Private villa/swimming pool in Tuscany

The Owl: view, pool and garden

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Casa di Lyndall - Entire house with exclusive pool

Antico Borgo Ripostena – n. 8 Old House

Gaiole in Chianti Poggio Casabianca

House Rigomagno Siena
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Traditional Apartment with Patio and Garden View

Cottage 48 sqm, swimming pool, relaxation, surrounded by greenery

Adalberto Apartment inside the Manor of Fulignano

Spinosa Apartment in Podere Capraia

House between Firenze, Arezzo, chianti e Siena

Podere Cupiano "La Costa"
Home rentals with a private pool

Sole by Interhome

La Felcaia by Interhome

Tuscan Villa Featured Conde Nast Best Villas Italy

Podere Vignali by Interhome

Tassinaia by Interhome

Podere San Lorenzo by Interhome

Charming villa in the Chianti hills

Meridiana by Interhome
Quick stats about holiday rentals with a pool in Monticiano
Total rentals
50 properties
Nightly prices starting at
$104 SGD before taxes and fees
Total number of reviews
450 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Wifi availability
30 properties include access to wifi
Destinations to explore
- Villa rentals Monticiano
- Rentals with a fireplace Monticiano
- Flat rentals Monticiano
- Rentals with outdoor seating Monticiano
- Rentals with a washing machine and dryer Monticiano
- Family-friendly rentals Monticiano
- Rentals with a patio Monticiano
- Smoking-friendly rentals Monticiano
- House rentals Monticiano
- Pet-friendly rentals Monticiano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Gulf of Baratti
- Uffizi Gallery
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiaggia di Capo Bianco
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Spiaggia della Padulella
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Zuccale