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Holiday rentals with a pool in Santa Maria a Monte

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Santa Maria a Monte

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment in Noce
5 out of 5 average rating, 172 reviews

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. The apartment is furnished in the perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and thoughtful furnishings and products from local artisans that will help you have a pleasant stay . In the large outdoor courtyard you'll find a salt pool on a panoramic terrace with wonderful views of castle hills and vineyards with breathtaking sunsets.

Top guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano
4.98 out of 5 average rating, 113 reviews

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

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.

Top guest favourite
A spacious living area is furnished with a dining table and four chairs, complemented by a cozy sofa. Large windows offer views of the surrounding landscape, while subtle natural light filters through textured shades. A television is mounted on the wall, with a glimpse of an elegant bathroom in the background.
Loft in Scandicci
4.98 out of 5 average rating, 127 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 125 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favourite
A rustic dining area features a large wooden table set for meals, complemented by transparent chairs. A cozy fireplace, built into a stone wall, adds warmth to the space. Soft lighting is provided by hanging fixtures, enhancing the inviting atmosphere.
Flat in Sorana
4.95 out of 5 average rating, 212 reviews

Casa Gave - Nature and relax in Tuscany

The house consists of two apartments obtained from a wing of the "Gave" manor house located in Sorana, a small village in the heart of "Svizzera Pesciatina" in Tuscany. The house is ideal for those looking for relax in an atmosphere impossible to find in the most famous tourist locations. Surrounded by terraces where the olive trees are grown and open on the hillside offers a large fenced garden to allow you and your pets to spend a pleasant holiday.

Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano
4.96 out of 5 average rating, 190 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Top guest favourite
A serene outdoor view features olive trees dotting a grassy area. A few lounge chairs are arranged by the pool, which reflects the soft hues of early morning light. A mist envelops the landscape, enhancing the tranquil setting.
Farm stay in Lastra a Signa
4.99 out of 5 average rating, 158 reviews

Flat for 4 with garden & pool in agriturismo

We have created an intimate and exclusive environment, which can accommodate a maximum of 10 guests, where you can find a feeling of tranquility and freedom. The 70 square meter Rasty apartment is located on the ground floor, it is spread over two independent bedrooms and can accommodate up to four people, with four-poster beds, garden view, bathroom, living area and kitchen with fully equipped kitchenette.

Top guest favourite
A serene view of a crystal-clear swimming pool is featured, with comfortable lounge chairs arranged around it. In the background, a charming stone villa is set among lush greenery, providing a peaceful ambiance. The area is well-maintained, emphasizing an inviting outdoor setting.
Villa in Orentano
4.96 out of 5 average rating, 107 reviews

Charming Villa in Stone in Tuscany, Borgo ai Lecci

The location, easily accessible, is perfect for visiting the main attractions in Tuscany: the cities of art, the old villages, beautiful landscapes and many other points of interest in this amazing region. Or relax and feel like you are at home. This charming well-maintained Villa in Stone is part of a complex of three buildings used for higher-level holiday homes.

Guest favourite
An outdoor dining area features a spacious wooden table surrounded by dark wooden benches. The space is partially shaded by a terracotta-tiled roof, and greenery can be seen in the background, creating a natural setting for meals or gatherings.
Cottage in Provincia di Lucca
4.92 out of 5 average rating, 112 reviews

Tuscan Cottage with swimming pool Pet Friendly

A typical Tuscan farmhouse, built as a refuge for pilgrims on the Via Francigena in 1032 AD. Cozy and warm, ideal for 4 people but also suitable for 6, it welcomes your four-legged friends with pleasure! Located in a strategic area, a stone's throw from the SP1, the road that connects Camaiore to Lucca. Very easy to reach, from here you can visit all of Tuscany!

Top guest favourite
The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.
Farm stay in Pisa
4.99 out of 5 average rating, 313 reviews

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.

Top guest favourite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay in Palaia
4.98 out of 5 average rating, 179 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded 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 Santa Maria a Monte rentals with a pool

Quick stats about holiday rentals with a pool in Santa Maria a Monte

  • Total holiday rentals

    Explore 20 holiday rentals in Santa Maria a Monte

  • Nightly prices starting at

    Santa Maria a Monte holiday rentals start at $105 SGD per night before taxes and fees

  • Verified guest reviews

    Over 330 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    20 of Santa Maria a Monte holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Santa Maria a Monte rentals

  • 4.8 Average rating

    Santa Maria a Monte stays are highly rated by guests – averaging 4.8 out of 5!

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