
Holiday rentals with a pool in Monticiano
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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.

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.

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.

Infinity view
Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

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).

Podere La Castellina - No. 3 JUNIPER
Stone and brick apartment inside the "Podere la Castellina" in the magnificent natural park of Montagnola Senese. The apartment located on the second floor can comfortably accommodate 5 people (4+1) and includes: - large living room with fireplace and sofa bed - kitchen - 2 bedrooms: one with a double bed and one with two single beds - two bathrooms Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

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.

Il Castello di 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.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

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
Popular amenities for Monticiano rentals with a pool
House rentals with a pool

Casina in campagna Podere Scorno con piscina

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Private villa/swimming pool in Tuscany

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Explore Chianti from a Charming Stone House

Country chic house in a village,private pool,wiFi

Nada Home
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Lornano Winery Farm - Villa ''Trebbiano''

Scenic Stilish Country

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Poggiolieto Suite - on hills 10' from city center

Manuela apartment with pool in farmhouse
Home rentals with a private pool

Villa Pergo is an ancient charming country villa

Esplora la natura al centro di Vigneti Chianti

Historic home with exclusive pool

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

"La Falterona" Villa 15 km Florence

TREEhouse / casaBARTHEL
Quick stats about holiday rentals with a pool in Monticiano

Total holiday rentals
Explore 30 holiday rentals in Monticiano

Nightly prices starting at
Monticiano holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 440 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
30 of Monticiano holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Monticiano rentals

4.8 Average rating
Monticiano stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a patio Monticiano
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- Rentals with a fireplace Monticiano
- Rentals with a washing machine and dryer Monticiano
- Rentals with outdoor seating Monticiano
- Family-friendly rentals Monticiano
- Villa rentals Monticiano
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- House rentals Monticiano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Lake Trasimeno
- Marina di Cecina
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Spiaggia Di Barbarossa
- Avignonesi Winery Fattoria Le Capezzine
- Piazza della Signoria





