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Vacation rentals with a pool in Santa Maria a Monte

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Popular amenities for Santa Maria a Monte rentals with a pool

House rentals with a pool

Guest favorite
A charming vacation home is displayed with a landscaped yard featuring lush green grass and mature olive trees. Two umbrellas provide shade over the outdoor seating. A decorative stone feature adds character to the garden, accessible by a paved pathway.
Home in Castel del Bosco
5 out of 5 average rating, 12 reviews

Melody house dependance casa vacanze

MartaRating, 5 stars9 months ago
“The small house with the fully fenced garden was perfect for our stay. Everything you need is furnished with care and convenience. Cinzia is an incredibly kind and helpful host. It goes above and beyond to make the stay as pleasant as possible and responds immediately to requests. We were particularly impressed by the well-stocked refrigerator with plenty of drinks and food. We spent 10 wonderful days there with our two dogs, who were very warmly welcomed. The Jacuzzi was always very clean and was regularly checked and cleaned by the host. Cinzia is always available when needed, but also respects the privacy of her guests. We felt completely comfortable and can highly recommend the house. ”It was very nice
Top guest favorite
An aerial view depicts the medieval village of Palaia, characterized by its charming terracotta rooftops and lush greenery. The surrounding Tuscan hills create a scenic backdrop, with a glimpse of the communal garden featuring a swimming pool. The landscape reflects the authenticity of the area.
Home in Palaia
4.98 out of 5 average rating, 43 reviews

Conte Martini House

NicolasRating, 5 stars5 days ago
Wonderful place to either lay back and enjoy the picturesque-postcard view from the comfort of your front yard or the pool (which was refreshingly cool in June), or to go further explore Tuscany locations within reach. The house was beautiful, clean and equipped with everything you could ask for, ie a quiet and air conditioned bedroom, kitchen with a gas stove, fridge and a wood fired bbq and a jacuzzi + comfy seating outside. Shops, restaurants and bars are all within walking distance, max 10 minutes. Andrea is a fantastic host who clearly cares about providing the best possible stay for her guests, which she did. Whenever we return to Tuscany, we will definitely make sure to stay here at Palaia again.
Top guest favorite
The exterior of a two-story yellow house is displayed, featuring green shutters and a charming balcony adorned with flower pots. Stone accents at the base contrast with the bright walls. A pathway leads to the entrance, surrounded by greenery and colorful flowers.
Home in Gallicano
4.99 out of 5 average rating, 104 reviews

Serenella

RobertRating, 5 stars5 days ago
Ilaria's home and garden make you feel like you are "Sitting on Top of the World". Like in the Walter Vinson and Lonnie Chatmon song. Time flew in Perpoli, like the swallows in the clear blue sky that embraced the mighty mountains at the horizon. The house is intimate, like the village whereas the garden is a never ending story. Ilaria is a super friendly host who was easy to communicate with and (together with her father's art) has given this place a piece of magic. No doubt we would love to come back
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 71 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars1 week ago
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Guest favorite
Home in Certaldo
4.87 out of 5 average rating, 63 reviews

Paluffo Tower House

AzaleaRating, 5 stars1 month ago
Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.
Top guest favorite
A scenic view showcases rolling green hills of Tuscany, dotted with olive trees and distant houses. The pool area, adorned with a lounge chair and shaded by a white umbrella, invites relaxation. The blue sky is streaked with soft clouds, enhancing the tranquil landscape.
Home in Morrona
5 out of 5 average rating, 29 reviews

Villino Isotta (exclusive private villa)

NeilRating, 5 stars1 week ago
We were an extended family of eight. The accommodation can only be described as perfect for us. The views were amazing and it was just so peaceful. We enjoyed the pool and the short trips to many restaurants and surrounding villages. That said, we spent most mornings and evenings soaking up the views across the valley to Volterra and beautiful villages dotted on the hillside. Andrea takes huge pride in being accessible and instantaneously responsive. A pleasure to deal with. A small bar / cafe across the road took care of morning coffee’s and any gelato pangs. Thank you Andrea, you made our stay so very memorable. Our only disappointment was leaving!!
Guest favorite
A rectangular private pool is surrounded by a grassy area and olive trees, providing a serene outdoor setting. Six lounge chairs are placed neatly around the pool, offering space for relaxation. The sky is partly cloudy, enhancing the natural beauty of the surroundings.
Home in San Miniato
4.92 out of 5 average rating, 102 reviews

Lovely house in a scenic and paiceful location

CedricRating, 5 stars1 week ago
We stayed at Maria’s home for a long family weekend with 6 adults. There is quality ac, 3 bathrooms and 3 good double beds. The private pool is very good with comfortable lounge chairs. Cooking easy in the fully equipped kitchen. Recommended!
Guest favorite
A newly constructed swimming pool features clear turquoise water, surrounded by landscaped grass. Sun loungers sit next to the pool, while manicured hedges and olive trees frame the space, offering a serene outdoor environment. The house stands in the background under a clear blue sky.
Home in Palaia
5 out of 5 average rating, 41 reviews

Casolare Ceppeto di Casapieri - Italy, Pisa

MarcRating, 5 stars1 month ago
Riccardo is the owner of the Airbnb who we dealt with from the day of our check in to the check out. Even with the language barrier, he could not be more helpful, polite and a general great person. Our family of eight plus a one year old felt at home. Him and his wife even cooked us a home cooked meal! After a long day of travelling, this was a good base to Ret and relax. Highly recommend!

Condo rentals with a pool

Superhost
A small outdoor table is set for two on a private terrace, featuring a mosaic surface. Two glasses of red wine and a plate of snacks sit on the table. The view includes rolling hills, olive trees, and distant homes, creating a serene countryside backdrop.
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment.

TomRating, 5 stars4 days ago
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.
Guest favorite
A spacious pool is situated within a well-maintained garden, surrounded by green hedges and cypress trees. Sunlight reflects off the clear water, inviting relaxation. Lounge chairs are placed near the edge of the pool, offering a comfortable space to enjoy the serene landscape.
Condo in Asciano
4.91 out of 5 average rating, 151 reviews

Loggiato 3 apartment in Tuscany near Siena

TamarRating, 5 stars3 weeks ago
We had a great stay in Francesca's agriturismo. beautiful place with breath taking views. the place was very clean and tidy and it had all we needed and much more. it was a good base for traveling the area. take a ride on the SP146 - you won't regret it! all in all this place is highly recommended! wish i would visit here again. Toscany is soo beautiful.
Guest favorite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars3 weeks ago
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.
Guest favorite
A view through an ornate lattice structure reveals a doorway leading to a bright interior. Natural light filters into the space, highlighting its warm tones. The open door frames a scenic landscape beyond, suggesting a connection to the outdoors.
Condo in Buti
5 out of 5 average rating, 10 reviews

Cima alla Serra Farmhouse - "Leccino"

JacobRating, 5 stars2 weeks ago
We had a couple of fantastic days up in the mountains at Cima alla Serra. We sat every night on the terrace and enjoyed the view and the tranquility, and during the day you could relax by the pool, which was fantastic. Giovanna and the staff on site were very helpful and we are so happy with our stay. Although it is relatively close to Pisa, you should have a car, which we were recommended. We hope to have the opportunity to come back again! Thanks for a couple of nice days :)
Guest favorite
An exclusive outdoor area features a small wooden pool surrounded by a sun deck. Two colorful lounge chairs in red and blue are positioned nearby, complemented by lush greenery and olive trees, creating a serene natural setting.
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 470 reviews

Casa Rebecca with a small private pool

SophieRating, 5 stars2 weeks ago
Amazing place !! It really worth !
Guest favorite
Condo in Rifredi
4.92 out of 5 average rating, 166 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars2 days ago
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.
Guest favorite
A serene swimming pool is surrounded by lush greenery, featuring several lounge chairs arranged on a stone patio. Umbrellas provide shade next to the water, and a hillside dotted with trees and bushes rises in the background under a cloudy sky.
Condo in Casole d'Elsa
4.93 out of 5 average rating, 156 reviews

La Casetta

RamRating, 5 stars3 weeks ago
Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!
Superhost
An open space studio with a dining area is visible, featuring a table set for a meal. Above, a loft area houses a spacious bed, while wooden stairs lead to it. Natural light enters through windows, highlighting the rustic decor and inviting ambiance.
Condo in Fiesole
4.88 out of 5 average rating, 188 reviews

Poggiolieto Studio - on hills 10' from city center

BethRating, 5 stars1 week ago
We had a lovely a time at the property. It was exactly as described and had amazing views. The host was very welcoming and was exceptionally helpful. It is fairly easily to get to the city centre from the property. There are two fairly regular buses and we were able to use a maps app pretty successfully to predict travel times.

Home rentals with a private pool

Guest favorite
Home in San Casciano Val di Pesa
5 out of 5 average rating, 5 reviews

Sole by Interhome

MarkRating, 5 stars6 days ago
Incredible host. Incredible house. You feel like you are inside a postcard. The most beautiful views are all around you. We did not want to leave. Just breathtaking.
Guest favorite
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars1 month ago
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!
Guest favorite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 192 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars5 days ago
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!
Superhost
An elegant stone cottage is surrounded by lush greenery, featuring multiple levels and outdoor steps leading to a private swimming pool. The structure showcases rustic architecture with clay tile roofs, large windows, and a tranquil setting in the countryside.
Home in Pescia
4.86 out of 5 average rating, 21 reviews

Aurora by Interhome

NatalieRating, 5 stars1 week ago
We had a lovely week at this place. In particular, the outdoor area was fantastic! Thank you and happy to come back!
Superhost
Farm stay in Sovicille
5 out of 5 average rating, 7 reviews

Private Tuscan Villa, pool,Hot Tub, near Siena

CharleneRating, 5 stars12 months ago
Fabio’s house was absolutely wonderful! Janine was super helpful, and the place was so clean and comfortable. It fit our 2 large families easily! Thank you for letting us stay and relax and take in the gorgeous countryside!
Top guest favorite
An outdoor dining area is presented, featuring a long wooden table surrounded by benches with cushions. Overhead, a pergola provides shade, complemented by pendant lights. In the background, lush greenery and rolling hills are visible, while a hammock is gently draped nearby.
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 47 reviews

Charming villa in the Chianti hills

JessicaRating, 5 stars3 days ago
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.
The spacious living and dining area features a large table surrounded by wooden chairs. Arched doorways lead to the garden, while natural light floods the room, highlighting the wooden beams and tile flooring.
Home in Montopoli
5 out of 5 average rating, 6 reviews

La Gora by Interhome

PaulRating, 5 stars1 month ago
This place is just the ticket for tranquility and peace, great family vacation it the middle of a motorcycle tour to the south. Giancarlo is the friendliest chap and very helpful. We had a day in the pool too which was cool only being the end of April. Over all a fantastic stay and will try and return and recommend to friends
Guest favorite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 96 reviews

Casa Luigi Suite with exclusive pool

KatieRating, 5 stars2 weeks ago
We had an amazing stay here! The property is beautiful: great views, flowers and lemon/orange trees were blooming, and the pool was great plus super clean! The bnb was cozy with traditional Tuscany vibes. Giovanna and Luigi were amazing! Super friendly, loving, helpful, and funny 😁 highly recommended if you're looking for a peaceful country setting!

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    250 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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