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

Total vacation rentals
Explore 20 vacation rentals in Santa Maria a Monte

Nightly prices starting at
Santa Maria a Monte vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

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

Wi-Fi availability
20 of Santa Maria a Monte vacation rentals include wi-fi 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!
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.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. 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 pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 352 reviews
17th Century converted convent with olive grove
Away from it all in the peace and tranquility, yet 5 minutes from town. Escape the heat with the breeze in the hills and enjoy the nature in our beautiful rustic home. whole ground floor accommodation includes an enormous lounge area, well-equipped kitchenette, a family bedroom with bunk beds, and a further double bedroom. Beautiful lounge area with stunning views, and an ancient spring-fed swimming pool ( May-Oct) Pisa (+ airport) 15 mins Lucca 30 mins Florence 50 mins Train/bus 5 mins
4.92 out of 5 average rating, 107 reviewsLe Maggioline Your Tuscany country house
Nestled among serene olive groves, this charming, fully renovated Italian home combines rustic elegance with modern amenities, making it the perfect retreat. The house features four en-suite bedrooms with stunning panoramic views, a spacious terrace with a covered veranda for al fresco dining, a BBQ, and a newly updated saltwater pool (2023), open mid-April to October. Guests rave about evenings at the long table, savoring local wines while watching breathtaking sunsets. A true Tuscan escape!
4.98 out of 5 average rating, 142 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
4.98 out of 5 average rating, 127 reviews
Le Querce, ap. "Rosmarino", relax in Tuscany!
The new "Le Querce" apartments are located on the ground floor of a villa located on a three-hectare farm with olive grove and orchard, characterized by the presence of groves of tall oaks. The accommodations are apartments of about 60 square meters each, with a front porch for personal use of about 20 square meters overlooking the infinity pool, which is for common use (50 square meters), with sun loungers and umbrella available. Guests can enjoy free, unattended private parking.
4.93 out of 5 average rating, 43 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. We can also provide cots, cribs, baby bed, high chairs at the cost 10 euro each per day to be paid in cash locally.
4.97 out of 5 average rating, 116 reviews
Casale I Lecci – Papavero
75 sqm apartment, first floor, kitchen/living room with sofa bed, bedroom with double bed, triple bedroom with a double bed and a single bed, bathroom with shower. The property, recently renovated, is located on the hill about 1 km from the small medieval historic center of Santa Maria a Monte, in a very favorable position to visit the most important art cities of Tuscany. The farmhouse contains 4 independent apartments, equipped with all the necessary amenities.
4.89 out of 5 average rating, 37 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, 107 reviews
Lovely house in a scenic and paiceful location
This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.
4.93 out of 5 average rating, 123 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
4.96 out of 5 average rating, 146 reviews
Countryside Dream farm in Tuscany
Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm 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.
4.98 out of 5 average rating, 201 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.
4.99 out of 5 average rating, 338 reviewsPopular amenities for Santa Maria a Monte rentals with a pool
House rentals with a pool

Frontemare house with exclusive sea access
4.95 out of 5 average rating, 111 reviews
Hilltop Views From a Historic Tuscan Home
4.99 out of 5 average rating, 110 reviews
Infinity pool in Chianti 1
5.0 out of 5 average rating, 143 reviews
I Limoni Apartment in Tuscany
4.85 out of 5 average rating, 151 reviews
Coppori Estate Dependance
5.0 out of 5 average rating, 110 reviews
Iris vacation home with pool
4.96 out of 5 average rating, 92 reviews
Redolina House in the Hills with pool 6/8p.
5.0 out of 5 average rating, 27 reviews
OttoPini Beautiful villa, Montecatini Terme
5.0 out of 5 average rating, 23 reviewsCondo rentals with a pool

Bel Canto Lari, exclusive, rural, Tuscan retreat
4.97 out of 5 average rating, 105 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 151 reviews
Apartments Le Palme
4.92 out of 5 average rating, 102 reviews
Vintage Residence with Pool in Chianti
4.96 out of 5 average rating, 148 reviews
Charming Tuscan home with pool, garden & Air-Con
4.88 out of 5 average rating, 100 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Tenuta di Pomine Certaldo (Fi) Edera Apartment
4.85 out of 5 average rating, 110 reviews
Belvedere
4.91 out of 5 average rating, 180 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
TREEhouse/casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 76 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Gorgona
- Parco dell'Orecchiella
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Val di Luce
- Pitti Palace





