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Villa vacation rentals in San Benedetto del Tronto

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Popular amenities for San Benedetto del Tronto villa rentals

Private villa rentals

A spacious outdoor area features a heated swimming pool surrounded by a large terrace. Sunbeds and a shaded seating area are visible, with expansive views of rolling hills and distant mountains in the background under a clear sky.
Villa in Colle Petitto
4.58 out of 5 average rating, 26 reviews

Modern villa, with panoramic view.

FlorianRating, 5 stars10 months ago
Great house, quietly located with lots of privacy, great views. A few degrees cooler than on the beach and a slight wind, so even in August high summer it was great to bear. Lots of seating options around the house. Mega great pool with diving board. The house offers everything you need. We would definitely come back.
A stone pathway illuminated by soft lighting leads through landscaped gardens. The path is flanked by various plants, including tall agave and blooming flowers. Rustic buildings can be seen in the background, with warm light spilling from windows against a twilight sky.
Villa in Monte San Martino
5 out of 5 average rating, 3 reviews

Belvilla by OYO Santa Caterina.

FrancescaRating, 5 stars7 months ago
Well, what can I say.. a unique experience! The owners were very kind, we felt right at home. Attention to detail, friendliness, punctuality, availability. The house is beautiful,the rooms are picturesque,the landscape is breathtaking. We will definitely be back!!
Superhost
A spacious living area features large windows allowing natural light to fill the room. Stylish furniture is arranged around a circular coffee table, while vibrant floral wallpaper and colorful accents create an inviting atmosphere. A view into the garden is visible through the glass doors.
Villa in Francavilla al Mare
5 out of 5 average rating, 5 reviews

Seaside villa

AlexandraRating, 5 stars22 months ago
We stayed at the Enrico apartments with two families. this is a great place for kids. the sea is very close. cozy courtyard for evenings. comfortable beds and large space in the dining room. the only inconvenience is one bath for all. but we got through it 🤣
A refreshing pool area is surrounded by lush greenery, featuring several lounge chairs beneath a large umbrella. Olive trees provide shade, and the pool area is bordered by well-maintained lawn, inviting relaxation in a tranquil outdoor setting.
Villa in Marche
4.67 out of 5 average rating, 3 reviews

Panoramic villa with pool and gym

KlaraRating, 5 stars21 months ago
everything was absolutely perfect. Beautiful nature. Only for guests who have a car at their disposal. Beautiful large pool. We were very satisfied with the whole family
Guest favorite
An outdoor terrace is depicted with a dining table and four chairs, offering a panoramic view of the sea and surrounding hills. A decorative bowl sits at the center of the table, while a potted plant adds a touch of greenery to the space.
Villa in Campofilone
5 out of 5 average rating, 8 reviews

Terrace overlooking the sea with swimming pool IT109004C2C9M2E2CF

DaniƫlleRating, 5 stars10 months ago
The home is beyond amazing! In terms of cleanliness, best to date. But also the location, facilities and decor more than we had hoped. The two bathrooms and the pool pure luxury. Owners are super friendly, helpful and great in terms of communication. Upon arrival, a beautiful package with tasty things and bottle of wine and on farewell again surprised with a farewell gift. Incredibly sweet. A vacation to remember.
The image shows a sunlit area featuring a swimming pool surrounded by natural greenery. A deck area with lounge chairs and a large umbrella is visible, providing a space for relaxation. The villa's stone facade and outdoor seating area can be seen in the background.
Villa in Montegranaro
4.63 out of 5 average rating, 8 reviews

Villa Martin with private pool for 5 people

MarcoRating, 5 stars10 months ago
Such a pretty place! Pool is huge! Kitchen is well equipped Airco upstairs works good Beds are really nice and comfy! Communication with the company that manages the property is fast, professional and nice. Had an amazing stay
Guest favorite
The exterior of the house showcases a two-story structure with a staircase leading to the second level. A covered seating area is set up in the foreground, surrounded by greenery. A spacious driveway made of cobblestones adds to the inviting atmosphere.
Villa in Cupra Marittima
4.71 out of 5 average rating, 17 reviews

villa surrounded by greenery

HanieRating, 5 stars9 months ago
Luisa and Paulo made it possible for us to have a wonderful vacation, the house is really very large and quietly located, the surroundings very quiet and at the same time everything quickly accessible, unfortunately only by car. Apart from the beautiful beaches, we did a lot in the area during the time, even a visit to Rome was still in it, I would definitely maybe come back in the next few years, Regards Family Hanie
A tranquil infinity pool is seen overlooking the Adriatic Sea, with uninterrupted views of the horizon. The pool's water appears calm, and the clean, white tiles surrounding it enhance the bright and open atmosphere. A clear blue sky complements the serene setting.
Villa in Ripari Bardella
4.86 out of 5 average rating, 7 reviews

Stunning design villa with unique 180Āŗ sea views

RudyRating, 5 stars22 months ago
For me and my family this was one of the most relaxing vacations in one of the most beautiful homes we have ever had. Tina, who manages the house, is very responsive and a small problem with the hot water was fixed immediately. She knows the area very well and has lots of good recommendations. And if you ask nicely, she will gladly reserve a table in one of the many restaurants where no other language is spoken except Italian. You should also be prepared for hot weather and that the house has no air conditioning. I could only sleep badly at night because of the hear and you didn't want to open the windows wide because of the lack of mosquito nets. And if you are tall - like me - you should know that the beds are only 190 cm long. For families with small children I would not recommend the house. The two bedrooms in the Cube are not connected with each other or with the main house and up at the pool are few places where small children could fall off and hurt themselves badly.

Luxury villa rentals

Top guest favorite
A private pool is surrounded by lounge chairs and umbrellas, set within a gravel patio. Lush greenery and trees frame the area, with a farmhouse visible in the background against a clear blue sky.
Villa in Macerata
5 out of 5 average rating, 7 reviews

Italian Idyll, stunning views, pool, play-den.

GuidoRating, 5 stars10 months ago
Casa Lola proved to be a fantastic stay. The views from the house are spectacular and the amenities were of a very high standard. We much enjoyed the pool, the large kitchen and the various terraces. A great space for a large group to have a very relaxing holiday. Victoria was extremely helpful with local tips and introductions to some of her neighbours to help us out with various requests (one of her neighbours makes a great lasagne). All in all a great stay, and we might have to repeat the experience sometime.
A private swimming pool is surrounded by a spacious deck equipped with lounge chairs. The clear blue water reflects the sky, while lush greenery and distant views of the hills and Adriatic Sea create a serene setting.
Villa in Cupra Marittima
4.88 out of 5 average rating, 8 reviews

Family villa,pool,hilltop, sea Wi-fi Air-co EV cha

JulietRating, 5 stars11 months ago
This villa and its surrounding area is absolutely stunning. We had fresh organic tomatoes, figs, pears, peaches and apricots ready to pick and eat, not to mention the wine from Tommaso’s vineyard!! The chickens gave hours of entertainment to the little ones. The villa itself is large with all necessary amenities and the BBQ area a perfect space for al fresco dining. The pool is dreamy, large with spectacular views out to sea. Tomato was a wonderful host, always on hand for any questions and recommendations. We will definitely be back, it’s a fabulous place to relax in the peaceful Italian countryside yet a five minute drive to the beach - perfectto!!
Guest favorite
A spacious outdoor pool is surrounded by a well-maintained patio area. Comfortable loungers and umbrellas provide shade. Lush greenery and blooming flowers frame the scene, while the villa's rustic faƧade is visible in the background, enhancing the serene outdoor setting.
Villa in Civitanova Marche
5 out of 5 average rating, 20 reviews

Villa with private pool 500 meters from the beach

TeriRating, 5 stars1 week ago
So pleased with our stay at Sara’s. From beginning to end Sara was always responsive and helpful. The home was clean and comfortable and the views of the sea from every room were amazing. We did not expect to use the pool very much but in the end used it everyday for a cool dip in the evening. Hope to come back someday!!
A spacious villa with a modern rustic design is set against a panoramic backdrop of rolling hills. A turquoise swimming pool is surrounded by a well-maintained lawn and landscaped gardens, creating a serene outdoor space. Nearby, fields and olive trees extend towards the horizon.
Villa in San Benedetto del Tronto
5 out of 5 average rating, 7 reviews

Modernized rustic villa with enchanting views

FaisalRating, 5 stars9 months ago
We couldn’t recommend Villa Rustica highly enough. The villa itself is beautifully furnished and spotlessly clean. It contains most, if not all, amenities that one would need including coffee machine, garage and a well stocked utility room. The villa is located in a private location with absolutely no disturbances and is in easy reach of shops, restaurants and the seaside. The views from the villa, especially poolside, are spectacular! A huge thank you to Marco, Melissa and Nino. As hosts they could not have been more accommodating, warm, friendly and responsive. They have built something truly special. As a family we’ve had a pretty tough 12 months, but Villa Rustica provided a perfect backdrop for us to relax and unwind and enjoy each other’s company. Thank you again Marco, Melissa and Nino we’d love to visit again!
Top guest favorite
A refreshing swimming pool is surrounded by sun loungers and a shaded area. A small blue table with chairs is positioned nearby, offering a place to relax. Lush greenery frames the view of rolling hills under a clear blue sky.
Villa in Castignano
5 out of 5 average rating, 16 reviews

Lemonvilla - Panoramic position - Pool - 240sqm

ChristinaRating, 5 stars1 month ago
Stayed at the Lemonvilla while visiting family in Ripatranstone and San Benedetto. The villa was absolutely gorgeous - photos do not do justice. Private and remote feeling (but still close to town) we felt at home staying at the villa. All 7 of us had enough space. Marcus was proactive and accommodating before the trip started - providing recommendations before we arrived. We hope to return!
A scenic view of rolling hills and mountains is captured, framed by vibrant greenery. A statue is positioned amidst lush plants, and colorful wildflowers add warmth to the landscape. The area appears tranquil and well-maintained, inviting relaxation and appreciation of nature.
Villa in Montefortino
5 out of 5 average rating, 13 reviews

VILLA - Tenuta Cerretino - swimming pool, tennis, billiards

MartineRating, 5 stars22 months ago
A beautiful house in stunning rural surroundings. This is the perfect house for those who want peace and quiet. Host Giampiero is an incredibly sociable guy who wants to provide the best experience when staying in his house. He responds quickly and fixes what's needed. The only thing I have to postpone on my stay was that it wasn't clear from the listing that there was an external annex with 2 beds. This annex should be upgraded due to a fairly extensive moisture issue. In addition, unfortunately, 8 persons received ear infection during the first week due to poor water quality in the pool. Overall, though, it was an amazing stay where Gianpiero really went above and beyond to make us feel comfortable.
The large pool is surrounded by landscaped gardens, with expansive views of the rolling hills and distant Sibillini Mountains. The farmhouse is nestled in the greenery, providing a serene countryside atmosphere, and an open field leads up to the property, enhancing the sense of tranquility.
Villa in San Ginesio
4.83 out of 5 average rating, 6 reviews

Luxury Villa with Pool, Stunning Location

AndrewRating, 5 stars21 months ago
We have been thinking of revisiting San Ginesio for many years and this year we went back. What a wonderful part of Italy staying in a lovely house. Set on a hillside with stunning views of the Sibillini mountains. The house is spacious with two large sitting rooms interconnecting with a large well fitted kitchen all with great views. The bedrooms, we only used two, we’re spacious and the beds comfortable. The house produces as excellent downloadable guide with everything you need to know about the house and area. The wonderful house manager, Monica, lives a few minutes away and is very quick to respond with any requests. We had a very happy week here.
A spacious villa with a warm-colored facade is set in a lush garden. Sun loungers line the grassy area in front, facing the inviting swimming pool. Tall trees provide shade, creating a serene outdoor space for relaxation and enjoyment.
Villa in Corridonia
4.92 out of 5 average rating, 13 reviews

Beautiful villa with pool and magnificent views

ReneRating, 5 stars4 weeks ago
Spacious, nicely renovated house, beautiful garden and large pool. Ideal for inland excursions. Recommended accommodation

Villa rentals with a pool

A tranquil swimming pool is set against a backdrop of lush greenery and a clear blue sky. The pool's calm waters reflect the surroundings, while decorative lanterns are positioned at the edge, enhancing the serene environment.
Villa in Provincia di Macerata
5 out of 5 average rating, 9 reviews

Villa Bentivoglio

MarcoRating, 5 stars9 months ago
Lovely place, in the Marche hills. Too lovely, so much so that we spent a lot of time relaxing in the Villa. Too bad about the unpaved Stradello that connects the main road to the villa. Super helpful and friendly host. HIGHLY RECOMMENDED
Villa in Sant'Angelo
4.8 out of 5 average rating, 5 reviews

Villa Vittoria - Vacation villa with a private poo

AxelRating, 5 stars7 months ago
Me and my family had a lovely stay at Villa Vittoria and in Colonnella. The house was incredibly big with lots of areas for hangouts, inside and in the garden. Riccardo was easy to communicate with ahead of the trip and very flexible and helpful in general. He gave lots of nice recommendations for us with things to do, see and places to eat. Riccardo had also arranged wine for when we entered the house which was a very kind gesture. We met Laura as well, a very kind and helpful person. All in all, the stay at Villa Vittoria was great - I would definitely recommend this place for families/groups of friends, and I hope to come back again!
Guest favorite
A rectangular swimming pool is surrounded by greenery, with steps leading down to a landscaped area. The pool's clear blue water reflects the clear sky above. A rustic stone house is visible in the background, framed by trees and flowering plants.
Villa in Sarnano
4.92 out of 5 average rating, 36 reviews

Colle della Sibilla – Country House

CristinaRating, 5 stars9 months ago
Excellent typical heart-shaped grandmother's cake that we found on our arrival, excellent mulled wine, fantastic swimming pool, the rooster's alarm clock led us every morning to a rural and relaxing life... a breathtaking view of the village and mountains and a spectacular orchard. In short, everything wonderfully exceeded expectations. Leaving was an effort :-) Thanks to Lucia for her great availability and hospitality. Cristina&Co
Villa in Staffolo
5 out of 5 average rating, 3 reviews

Casa Pilar 4+1,Emma Villas

ChristineRating, 5 stars13 months ago
Dear Lisa & Christian Back in cold Switzerland. We had such a beautiful, inspiring and nourishing week for body and soul in your lovingly designed paradisiacal Casa Pilar šŸ˜ Of course we enjoyed the pool, even at 19 degrees it was an experience to enjoy the 13 meter swimming pool. Stefan was more diligent than me - but I also made it twice šŸ™ The house has so much charm and radiates just as much warmth as Lisa & Christian. Thank you for the delicious welcome vegetables šŸ™ The house is very well equipped. We didn't miss anything. We will be back again. There is still a lot to discover by gravel bike or on foot. The many Colini's simply invite you to be outside in nature We wish you both a great time and hope that you won't be overrun with guests this year šŸ˜‚šŸ¤£šŸ˜‚ Graze mille for everything šŸ™ Stefan & Christine
A private swimming pool is surrounded by lush greenery and neatly trimmed hedges. Sun loungers are positioned nearby on a manicured lawn, while the villa's exterior showcases large windows and a balcony. A stone terrace leads to the pool area, enhancing the serene outdoor setting.
Villa in Macerata
5 out of 5 average rating, 4 reviews

Mia House Garden - Macerata, portion of a villa

ToniRating, 5 stars9 months ago
We stayed with Mariella for 2 weeks in her beautiful villa. The house impresses with its large rooms, everything you need is there. Everything was very clean and well maintained. There is also a barbecue in the garden. Mariella made every effort to make our stay unforgettable. She is a great host and had lots of tips for us on restaurants and places to visit. Unfortunately, we didn't manage to see everything, which means we have the goal of coming back again. Macerata is a small but very nice town with lots of good restaurants and bars. The villa is a little on the outskirts of the town, beautifully situated in a good residential neighbourhood. There is everything you need to live, supermarket and restaurants nearby. Thank you for the nice hospitality!
Villa in Amandola
5 out of 5 average rating, 3 reviews

Panoramic country villa with pool

TeresaRating, 5 stars46 months ago
A week of true relaxation! The house is very cozy, familiar and super stocked. The place is wonderful! Take a bathroom with Sibillini mountain views, unparalleled! Great location to get away from it all. Caterina is very available and flexible. We will definitely want to return during the sunflower flowering period! Highly recommended!
Guest favorite
A spacious stone farmhouse is set against a backdrop of mountains. The outdoor area features a swimming pool with clear water, surrounded by manicured grass and a wooden patio with a dining set, creating an inviting space for relaxation.
Villa in Farindola
4.96 out of 5 average rating, 27 reviews

Villa Barricello

DavidRating, 5 stars9 months ago
We loved everything about this place. It’s a beautiful building which has been exceptionally well restored. Great location. Extremely well equipped with everything you could want. Pool is a particular highlight.
The exterior of a modern villa is highlighted by a vibrant orange facade under a clear blue sky. A covered patio with outdoor dining furniture is visible, framed by lush green grass and blooming pink roses, creating a welcoming entrance.
Villa in Tolentino
5 out of 5 average rating, 4 reviews

Villa Parruccia with a pool and panoramic views

BeatriceRating, 5 stars1 week ago
We had a really nice weekend in this house with a pool. The apartment was clean and tidy. The outdoor spaces are truly beautiful: spacious, well-kept and perfect for relaxing, with a breathtaking view! We appreciated the access to the vegetable garden and orchard, a detail that really made a difference for us. Another positive note goes to the presence of Leo, the owners' dog, who is very well behaved. They kept us company 😊 Hosts have always been discreet but available when needed. The pool was at our complete disposal and we enjoyed a nice privacy throughout the stay. The area is very quiet, ideal for getting away from the routine. If we really have to find a small criticism, only a few basic items were missing, such as napkins and oil, but nothing that compromised the experience. Highly recommended for those seeking peace and nature!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Marche
  4. Province of Ascoli Piceno
  5. San Benedetto del Tronto
  6. Villa rentals