
Holiday rentals with a pool in Monticiano
Find and book unique homes with a pool on Airbnb
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 $98 AUD per night before taxes and fees

Verified guest reviews
Over 230 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Monticiano holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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.

LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.
FamilyLocationWi-Fi
4.93 out of 5 average rating, 145 reviews
Elegant farmhouse Siena
The 200-square-metre apartment is part of a 17th-century farmhouse. It comfortably accommodates 6 people, has 3 large bedrooms, a grand living room, a kitchen with a fireplace, two bathrooms and a breathtaking view of the Tuscan countryside stretching as far as Montalcino. From 1 April 2025, the municipality of Murlo has introduced a tourist tax of €1.50 per person per day. Children under 12 are exempt. The tax must be paid on arrival, in cash, and your passports will be requested at the same time.
FamilyLocationShared spaces
4.96 out of 5 average rating, 167 reviews
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.
FamilyLocationKitchen
4.97 out of 5 average rating, 161 reviews
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.
ValueLocationComfort
4.97 out of 5 average rating, 251 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
LocationFamilyCleanliness
4.95 out of 5 average rating, 146 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.
FamilyLocationCleanliness
4.99 out of 5 average rating, 116 reviews
Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.
ValueFamilyHiking
4.98 out of 5 average rating, 447 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 352 reviews
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.
LocationValueView
4.98 out of 5 average rating, 222 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.
ValueLocationKitchen
4.98 out of 5 average rating, 107 reviews
Tuscan Barn Apartment for 6 with panoramic pool
Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.
LocationValueHeating
4.89 out of 5 average rating, 100 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.
LocationValueCheckout
4.89 out of 5 average rating, 309 reviewsPopular amenities for Monticiano rentals with a pool
House rentals with a pool

Infinity pool in Chianti 1
LocationFamilyWi-Fi
5.0 out of 5 average rating, 143 reviews
Palazzo Monaci - Pool in the Crete Senesi
FamilyValueCondition
4.96 out of 5 average rating, 142 reviews
Cercis - La Palmierina
FamilyLocationLaundry
4.96 out of 5 average rating, 147 reviews
House Rigomagno Siena
FamilyLocationGetting around
4.96 out of 5 average rating, 125 reviews
Conca d'Oro villa with private pool, sleeps 4
LocationFamilyAir conditioning
4.92 out of 5 average rating, 173 reviews
Explore Chianti from a Charming Stone House
LocationValueLong stay
4.98 out of 5 average rating, 123 reviews
Country Rentals - La Canonica
LocationFamilyWalkability
4.86 out of 5 average rating, 101 reviews
Private Chianti Cottage, Garden & Vineyard Views
LocationFamilyTV
4.99 out of 5 average rating, 137 reviewsCondo rentals with a pool

La Casetta
LocationFamilyAccess
4.93 out of 5 average rating, 197 reviews
Apt.Panzanello-Panzano in Chianti
FamilyValueView
4.96 out of 5 average rating, 282 reviews
Charming Tuscan home with pool, garden & Air-Con
ValueLocationBathroom
4.87 out of 5 average rating, 101 reviews
The House in Chianti - IlVillinoFarmhouse
FamilyLocationTV
4.78 out of 5 average rating, 246 reviews
House between Firenze, Arezzo, chianti e Siena
LocationFamilyAccess
4.84 out of 5 average rating, 302 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
LocationFamilyBreakfast
4.97 out of 5 average rating, 151 reviews
Cupiano Farm "Querciolettaia/Legnaio"
ValueLocationNearby
4.96 out of 5 average rating, 57 reviews
Casa Bianchini | Duplex 6-bedroom apartment (12 +1
LocationValueDecor
4.93 out of 5 average rating, 58 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
LocationFamilyCheckout
4.98 out of 5 average rating, 218 reviews
Explore nature in the heart of the Chianti vineyards
LocationValueCheck-in
4.97 out of 5 average rating, 265 reviews
Casa Luigi Suite with exclusive pool
LocationFamilyBarbecue
4.95 out of 5 average rating, 122 reviews
Magnificent Tuscan Villa, amazing interiors & view
FamilyLocationOutdoor spaces
5.0 out of 5 average rating, 16 reviewsHistoric villa x8 with exclusive pool
FamilyLocationComfort
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
FamilyLocationGetting around
4.8 out of 5 average rating, 76 reviewsWp Relais Villa Vignalunga
FamilyLocationDecor
4.93 out of 5 average rating, 117 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Spiaggia di Capo Bianco
- Mount Amiata





