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

Total vacation rentals
Explore 30 vacation rentals in Monticiano

Nightly prices starting at
Monticiano vacation rentals start at G$14,639 GYD per night before taxes and fees

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Over 230 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Monticiano vacation rentals include wi-fi access

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

4.7 Average rating
Monticiano stays receive an average rating of 4.7 out of 5 from guests
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 immerso nelChianti con piscina
Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults, with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards, with incomparable 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.

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.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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 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.

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.

Romantic apartment in the Tuscan village
The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

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.

Charming farmhouse with garden, views & pool
Escape to a bright two-bedroom apartment in a traditional Tuscan farmhouse with a private rooftop terrace, panoramic pool and breathtaking valley views. Surrounded by olive groves and silence, it's the perfect place to slow down, unwind and enjoy authentic Tuscany. For adults and teenagers aged 16+.
Popular amenities for Monticiano rentals with a pool
House rentals with a pool

Podere Scorno country house with swimming pool

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina

Borgo Ripostena – No. 5 Boathouse

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Relaxation and charm in the Chianti hills

Paluffo Tower House

Nada Home
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Agriturismo Poggio Bonelli, 2 people apartment

Cupiano Farm "Querciolettaia/Legnaio"

Scenic Stilish Country

Historic estate with views of Siena, 2 en-suite bedrooms, pool

Belvedere

Manuela apartment with pool in farmhouse

Charming Residence Castello di Orgiale near Siena
Home rentals with a private pool

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Wp Relais Borgo Vignalunga

Stone House with Exclusive Pool Codilungo in Chianti

Explore nature in the center of Vigneti Chianti
Historic villa x8 with exclusive pool

Villa Fonteintanata Ground floor
Destinations to explore
- Rentals with a fireplace Monticiano
- Pet-friendly rentals Monticiano
- House rentals Monticiano
- Rentals with a patio Monticiano
- Smoking-friendly rentals Monticiano
- Villa rentals Monticiano
- Rentals with outdoor seating Monticiano
- Apartment rentals Monticiano
- Rentals with a washer and dryer Monticiano
- Family-friendly rentals Monticiano
- 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
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Spiagge Bianche
- Piazza della Repubblica
- Parco delle Cascine
- Gulf of Baratti
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Spiaggia di Capo Bianco
- Spiaggia Di Barbarossa
- Piazza della Signoria





