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House vacation rentals in Pennabilli

Find and book unique houses on Airbnb

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Popular amenities for Pennabilli house rentals

House rentals with a pool

Guest favorite
A large swimming pool is surrounded by sun loungers and umbrellas, offering a serene space for relaxation. Lush greenery and gardens frame the setting, while the villa is visible in the background, enhancing the outdoor ambience.
Home in Loro Ciuffenna
4.92 out of 5 average rating, 39 reviews

"Tuscany Villa with PRIVATE pool"

LeonardoRating, 5 stars4 months ago
I recently stayed at this amazing Airbnb and couldn’t have been happier with the experience. The hosts were absolutely fantastic—kind, attentive, and incredibly helpful. They went above and beyond to ensure my stay was perfect, even recommending a stunning restaurant that became the highlight of my trip. The accommodation itself was spotless, cozy, and perfectly located, making it easy to explore the area. I truly felt at home and can’t wait to return. Highly recommend staying here if you’re looking for a memorable experience! Five stars all the way!
Superhost
A stone facade of the villa is revealed, showcasing a spacious outdoor area beneath an olive tree. A long dining table with chairs is positioned on a tiled patio, framed by potted plants. Windows allow natural light into the interior.
Home in Rapolano Terme
4.72 out of 5 average rating, 107 reviews

Breathtaking view. Indipendent portion of a villa

RafaelRating, 5 stars7 months ago
The three of us spent a week at Laura's place. Especially the location of the place is great! You have a beautiful view over the city and can walk to various restaurants, ice cream parlors, etc. All the necessary amenities were available, all rooms were clean, and communication with Laura was very quick and easy! Arrival and departure worked completely smoothly and easily.
Superhost
A shared swimming pool is surrounded by a fenced area, featuring several sun loungers with striped cushions and umbrellas for shade. Olive trees and lush greenery create a peaceful backdrop, while the clear blue sky adds to the serene atmosphere.
Home in Reggello
4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars7 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Top guest favorite
A well-maintained outdoor area features a private pool surrounded by a lush green lawn. A cozy villa can be seen in the background, complemented by tall trees and a relaxing ambiance. Lounge chairs are positioned near the pool, inviting leisure under the partly cloudy sky.
Home in Reggello
5 out of 5 average rating, 44 reviews

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.

MicheleRating, 5 stars1 week ago
Very nice place to stay in the hpgel of Tuscany. A little remote but we appreciated that. Lots of restaurants around the area with really very good food and absolutely good prices. Accommodation with a large garden, pool, air conditioning and heating. Well-maintained and clean. Chickens whose eggs we were allowed to get. Magena true always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We'll be back. Thanks Magena and Eduardo
Superhost
A spacious bedroom features high, arched ceilings with exposed brickwork. A large bed occupies the center, complemented by elegant wooden furniture, including a dresser and wardrobe. Soft lighting adds warmth, and a door leads to the adjoining space, enhancing the inviting atmosphere.
Home in Asciano
4.85 out of 5 average rating, 13 reviews

house with pool between Siena and Valdorcia

MatthewRating, 5 stars2 weeks ago
Had a wonderful 4 nights in this very peaceful villa in Tuscany. Check in with Ricardo was easy, very friendly. We had no problems in our stay so didn’t need to bother him, so while he lives on site it felt like our own villa for the whole time. The pool was very kindly opened early in the season for our kids to use. Wonderful views from the pool terrace. Only suggestion is for simple things like salt, pepper, balsamic etc to be left so to avoid every guest having to buy new. . But overall this was a 5 star stay and we would highly recommend, thank you!
Top guest favorite
A rustic farmhouse is surrounded by lush greenery, with a shaded terrace featuring comfortable seating and a view of the inviting pool. The roof showcases traditional tiles, complemented by stone accents and tall trees, providing natural shade and tranquility.
Home in Arezzo
5 out of 5 average rating, 33 reviews

Beautiful barn among the olive trees

TijmenRating, 5 stars6 days ago
We had a great stay for 2 nights when traveling to Sicily. Barbara and Gigi were very welcoming. The house was great, it was private, clean and spacious with a great interior. Our dog could walk freely in the garden. The pool was clean and used multiple times during the day.
Superhost
Home in Umbertide
4.69 out of 5 average rating, 16 reviews

Villa La Ginestra, private villa with pool

AlexandraRating, 5 stars7 months ago
Perfect oasis for a family vacation The location is simply magnificent – secluded and quiet, far away from the hustle of everyday life. The expansive property is a real highlight: there are beautiful pergolas that invite you to eat, play and relax outdoors. The pool is fantastic – it is cleaned daily, offers comfortable loungers and plenty of umbrellas. We especially appreciated that the entire property is fenced which makes it ideal for pets. The bedrooms are charmingly furnished, with comfortable beds that ensure a good night's sleep. The kitchen is well equipped and offers everything you need. The cleanliness was also great – with a thorough intermediate cleaning after a week. We would like to highlight the quick and competent response of all our questions, which made the stay even more pleasant. All in all it was the perfect place for an unforgettable family vacation that we can highly recommend.
Top guest favorite
A private swimming pool is surrounded by lush greenery, with a smooth stone wall bordering the area. Wooden lounge chairs are positioned nearby, offering shaded comfort under a wooden pergola. The turquoise water reflects the sky, creating a serene outdoor space.
Home in Citta di Castello
4.98 out of 5 average rating, 52 reviews

Country house with pool in northern Umbria bordering Tuscany

PawełRating, 5 stars8 months ago
Great house, where you have everything you need to feel relax and umbrian vibe. Very private and very close to nature. Giovanni is a very friendly host, thank you!

Weekly house rentals

Guest favorite
The outdoor area features stone walls and a well-maintained garden with various plants. A small deck chair is positioned for relaxing, with a sunny sky overhead. Shade is provided by large awnings, and the serene landscape includes green trees and a distant view of rolling hills.
Home in Urbino
4.91 out of 5 average rating, 32 reviews

Sant'Eufemia 13 - Farmhouse 4 km from Urbino

TeclaRating, 5 stars1 week ago
Mara is an attentive, helpful, generous and welcoming host. The place is beautiful, very quiet away from the chaos of the city. An experience to recommend
Top guest favorite
An appealing stone villa is framed by lush greenery and manicured hedges. A circular stone fountain is centered in a gravel area, surrounded by shrubs and trees. The sky is partly cloudy, providing a gentle light that enhances the natural beauty of the setting.
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars7 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
Top guest favorite
A spacious dining area showcases a wooden table surrounded by six chairs. A tall shelf holds decorative items and flowers, while light filters through sheer curtains, illuminating the room's warm tones and exposed beams on the ceiling.
Home in Pesaro
4.91 out of 5 average rating, 77 reviews

Beautiful house in the historic center a stone's throw from the sea

paulaRating, 5 stars7 months ago
We really enjoyed our stay here is Pesaro. The accommodation was really lovely and we felt very relaxed. Nice decor throughout and spacious enough for the whole family. Francesca was very responsive to any questions and had provided some lovely recommendations for local food. We would stay here again and highly recommend to anyone
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars1 week ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Guest favorite
A modern living-dining area features a light-colored sofa and a dining table surrounded by four chairs. The ceiling showcases exposed wooden beams, while natural light illuminates the space through a large window. A kitchen area with white cabinetry and appliances is visible in the background.
Home in Arezzo
4.91 out of 5 average rating, 86 reviews

La Casa di Daniele&Patrizia-Family, relax and view

LisaRating, 5 stars6 months ago
The views from this guest suite will be some of my favorite memories of Tuscany. I highly recommend going outside 30 minutes before sunrise to watch the sky change colors against the mountains while you take a deep calming breath looking across the valley below. The guest house is compact, modern, and clean. And Patrizia and her family are just next door, available and friendly if you need anything.
Guest favorite
A small covered patio area is presented with a white metal bench complemented by two soft cushions. The wall is painted in a warm orange hue, and a welcome mat is placed in front of the entrance door, enhancing the inviting space.
Home in Cesena
5 out of 5 average rating, 10 reviews

The other house

KarinRating, 5 stars1 day ago
Very nice house. You must look at all the photo’s than you see what beautiful house it is. Very Nice stay!
Superhost
A spacious living area features two comfortable sofas, a wooden desk, and a bookshelf filled with books. Natural light enters through large windows with white curtains, providing a view of the outdoor space. A tasteful floral arrangement decorates the coffee table.
Home in Gabicce Mare
4.93 out of 5 average rating, 14 reviews

The house on the Dolce Colle, within walking distance of the sea

JuergRating, 5 stars7 months ago
We (married couple and three dogs) had a great holiday experience in every respect in the little paradise of Lorenzo & Monica. The house: maintained with a lot of love, care and pride, offers space inside and in the garden as well as privacy. The location: on the small hill enough far away from the hustle and bustle of tourists at the bottom of the promenade, but close enough to the sea (300m, small road down the slope), surrounded by greenery and nature. The hosts: flexible, polite and communicative (Lorenzo, with him the booking was arranged) as well as charming, helpful and host from Passion (Monica, who lives next door with her family). Maybe it is better if we stop with the praise now because we would like to come back next year - and don't want there to be no more space...;-) Grazie mille, Monica e Lorenzo!
Superhost
A spacious dining area is highlighted by a large wooden table surrounded by chairs. Exposed wooden beams and an arched window frame contribute to the rustic charm. A glass door allows natural light to illuminate the room, revealing a comfortable seating area in the background.
Home in Molino Vitelli
5 out of 5 average rating, 3 reviews

2 / 8px house on Tuscan Borders

ElizabethRating, 5 stars3 weeks ago
Andrea's place was perfect for our short two night stay in the Niccone Valley, or fav area in Umbria. We were there in cooler weather and the floor heating took a bit to come on but once it did we were comfortable. I think it would be a great place in the warmer weather as the pool looked wonderful. The Niccone Valley is somewhat remote but with the location of this property you had the best of both worlds quick access to Umbertide and yet embedded in the valley. Would love to return in the warmer weather. Thank you Andrea!

Private house rentals

A stone house is set among lush greenery, providing a serene view of the surrounding hills. The pool is visible in the yard, with tranquil landscapes extending towards distant mountains under a clear blue sky.
Home in Umbertide
5 out of 5 average rating, 3 reviews

Casa Adriano

SebastienRating, 5 stars8 months ago
We stayed 2 weeks at 5 (2 adults and 3 children) The setting is idyllic. The house is large as well as the swimming pool. Alex and Prya are hypers responsive and do everything to ensure that the stay goes smoothly. Highly recommendable host and listing. What a positive thing. For owners of an electric vehicle, the property has a Tesla domestic terminal. Recharge of about 7km per hour. Umbertide has fast chargers in front of the COOP supermarket.
Home in Zollara
4.71 out of 5 average rating, 14 reviews

Ancient Stone Farmhouse by Interhome

KerrieRating, 5 stars7 months ago
This place is pretty special. This is a very old home so very charming but you do have to get used to the downstairs shower (tricky regulating water temp and slow draining shower floor). The upstairs bathroom is gorgeous with the best view, I just wish it had a shower curtain so the bathtub could also easily work as a shower. We took lots of photos of the beautiful old architectural details inside the home. We spend several afternoons lazing by the gorgeous pool in the lovely outdoor space. We even used the outdoor shower a couple mornings. We found everything we needed in the kitchen. We could sign in to our Netflix account to watch movies on the TV in the evenings after watching the gorgeous sunsets. The Grotto restaurant, not too far away by car, was fabulous.
The exterior view highlights a large swimming pool surrounded by well-maintained green grass and lounge chairs. The two-story house features a distinctive yellow façade and multiple outdoor seating areas under umbrellas, with countryside scenery visible in the background.
Home in Monte San Savino
5 out of 5 average rating, 5 reviews

La Salciaia by Interhome

DavidRating, 5 stars9 months ago
We had a great stay with friends and family! The house is big, the garden is superb (and large!) and the swimming pool was big and safe. The owners were also very reactive to our requests, and the chef option is highly recommended for at least part of the stay! Thanks again, and see you again soon.
An elegant entryway featuring a decorative chandelier above a round dining table set on a colorful area rug. Arched doorways lead to the living area, where natural light filters through large windows, illuminating the stone walls and terracotta tiles.
Home in Pieve a Presciano
5 out of 5 average rating, 3 reviews

Casavecchia by Interhome

NickRating, 5 stars19 months ago
Great holiday typical Toscan atmosphere.I strongly recommend,
A spacious two-story house is set against a clear blue sky, surrounded by lush greenery. A terraced flower bed features red roses, and a shaded area with an umbrella and seating is visible on the porch. A pathway leads to the entrance of the house.
Home in Pergine Valdarno
5 out of 5 average rating, 8 reviews

Pianelli by Interhome

DiegoRating, 5 stars22 months ago
The stay was amazing, the Host Luciano was very nice and forthcoming about any inquiry we had. I can recommend the place to anybody who wants to have a nice, chill time in the hills of central Tuscany.
Top guest favorite
A modern kitchen features a central island with an induction cooktop and seating for several guests. Gray cabinetry complements stainless steel appliances, including an oven and refrigerator. Natural light fills the space, highlighting the open-concept layout that connects to the living area.
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars6 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.
Top guest favorite
A two-story stone house is surrounded by lush greenery, showcasing a covered porch with chairs and a small table. Large windows with wooden shutters offer a glimpse of the inviting outdoor landscape, while the rustic stone exterior blends harmoniously with the natural setting.
Home in Montecchio
4.91 out of 5 average rating, 32 reviews

Private Tuscan country home with view near Cortona

RhodRating, 5 stars6 months ago
Suitable for those wanting a peaceful getaway in Tuscany which is close to Cortona and Castiglion Fiorentina. Great views over the valley to enjoy with public transport [ trains and buses] not far away to take you further afield. You do your own transport to get there as up a hill, which whilst walkable, but not with luggage. Modern kitchen, comfortable beds, good internet and a Smart TV ensure you don't miss your home comforts. But oh so peaceful!
Guest favorite
An interior view showcases a charming entryway framed by a stone arch. The double doors open to reveal a bright outdoor view filled with greenery. A coat rack stands nearby, while a lamp and a small table enhance the inviting atmosphere.
Home in Civitella Val di Chiana AR
5 out of 5 average rating, 17 reviews

Il Giglio Farmhouse by Interhome

Maria AlejandraRating, 5 stars2 weeks ago
Casale Il Giglio is a beautiful place and hosts Silvia, Gianlucca and Neri make the experience even better; they are thoughtful and kind and made our family of 4 feel right at home. It is just like the photos, if not better. It was a highlight on our trip and we hope we can go back!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Emilia-Romagna
  4. Province of Rimini
  5. Pennabilli
  6. House rentals