
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$14,644 GYD per night before taxes and fees

Verified guest reviews
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.

Ancient 17th-century farmhouse in Chianti, Tuscany
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and 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, with wonderful views of the castle, hills, and vineyards and breathtaking sunsets.
5.0 out of 5 average rating, 218 reviews
Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
4.99 out of 5 average rating, 113 reviews
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.
4.96 out of 5 average rating, 138 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.
4.97 out of 5 average rating, 160 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.
4.99 out of 5 average rating, 113 reviews
Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
4.98 out of 5 average rating, 216 reviews
Agriturismo La Villa - Il Castagno, 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.
4.98 out of 5 average rating, 218 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.
4.98 out of 5 average rating, 105 reviews
Typical Tuscan country house
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 just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.
4.99 out of 5 average rating, 431 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.
4.89 out of 5 average rating, 307 reviews
Appaloosa - Apartment for couples and families
Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.
4.86 out of 5 average rating, 122 reviews
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.
4.99 out of 5 average rating, 117 reviewsPopular amenities for Monticiano rentals with a pool
House rentals with a pool

LECCIONE RESIDENCE
4.93 out of 5 average rating, 143 reviews
Cercis - La Palmierina
4.96 out of 5 average rating, 144 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 136 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 122 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 122 reviews
Conca d'Oro villa with private pool, sleeps 4
4.92 out of 5 average rating, 172 reviews
Podere Scorno country house with swimming pool
4.93 out of 5 average rating, 143 reviews
Villa Lolù with private heated swimming-pool
4.97 out of 5 average rating, 159 reviewsCondo rentals with a pool

La Casetta
4.93 out of 5 average rating, 194 reviews
Loggiato 3 apartment in Tuscany near Siena
4.93 out of 5 average rating, 201 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 280 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 300 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 149 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 135 reviews
Cupiano Farm "Querciolettaia/Legnaio"
4.96 out of 5 average rating, 56 reviews
Large Apartment in a Villa, swimming pool, Siena
4.77 out of 5 average rating, 31 reviewsHome rentals with a private pool

Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 121 reviews
Esplora la natura al centro di Vigneti Chianti
4.97 out of 5 average rating, 264 reviews
Magnificent Tuscan Villa, amazing interiors & view
5.0 out of 5 average rating, 16 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 75 reviews
Villa il Palagio in the Tuscan countryside
4.98 out of 5 average rating, 41 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Stazione Santa Maria Novella
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Spiaggia di Capo Bianco
- Boboli's Garden
- Mount Amiata





