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Vacation rentals with outdoor seating in Castiglione della Pescaia

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Popular amenities for Castiglione della Pescaia outdoor seating rentals

House rentals with outdoor seating

Guest favorite
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
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
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, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 weeks 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!
Top guest favorite
A spacious bedroom features a large bed with a patterned coverlet. Two open doors lead to a private balcony with a table and chairs. Natural light floods the room, highlighting the scenic view of the surrounding hills and trees.
Home in Villa a Sesta
4.98 out of 5 average rating, 436 reviews

Raffaella's House in Chianti

AshleyRating, 5 stars1 week ago
Very peaceful and beautiful views from the rooms. Raffaella’s breakfast was very good and much appreciated! She gave amazing local food recommendations that are walkable from her house. She also helped us find parking in the city of Florence!
Guest favorite
A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Old House

LucyRating, 5 stars2 weeks ago
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)
Guest favorite
A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.
Home in Poggio San Marco
4.97 out of 5 average rating, 276 reviews

Charming converted Hayloft overlooking the Chianti Hills

AnhRating, 5 stars1 week ago
The house is located on Chianti which views to vineyard and olive yard, the most beautiful view for an airbnb. Everything is fully furnished, a lot of welcome foods and drinks. The hosts give clearly instruction and very responsive. It was a wonderful time spending our holiday there.
Guest favorite
A serene garden path is lined with lush greenery and gravel, leading to a modern entrance. A vine-covered trellis provides partial shade, while the surrounding foliage creates a tranquil atmosphere. The nearby architecture adds character to the outdoor space.
Home in Siena
4.91 out of 5 average rating, 333 reviews

Amazing Cott. in the heart of Siena

GrahamRating, 5 stars1 week ago
Great location only 2 minutes walk from the Cathedral. Accommodation is airy and well equipped with its own lovely garden giving you a great place to relax so close to the centre. Francesca was always available and made us feel very welcome. Have already recommended this property to our friends.
Top guest favorite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.97 out of 5 average rating, 170 reviews

Secret Garden Siena

DanielRating, 5 stars4 days ago
The Siena Secret Garden apartment was amazing. We loved the location, and it was quiet and comfortable and stocked with a lot of beautiful art, books, and movies. Would definitely stay here again!
Top guest favorite
A charming garden area features a round table surrounded by four wrought iron chairs. Vibrant flowers bloom in planters, and lush greenery adds to the tranquil environment. A rustic stone wall and traditional rooftops provide a picturesque backdrop, enhancing the sense of privacy.
Home in San Gimignano
4.99 out of 5 average rating, 190 reviews

Garden House

ShelseaRating, 5 stars1 week ago
We had an amazing time at Mario & Cristina’s place. The house was absolutely beautiful, (and has a really cool history; it was fun to stay in such a historic building) and the garden was so so lovely! (We loved hanging out with Signore Tartaruga! 🐢) Located right in beautiful medieval San Gimignano, close to everything you need (especially the world’s best gelato at Dondoli’s!) It was a wonderful stop on our honeymoon and San Gimignano will have a special place in our hearts forever! Grazie mille Mario e Cristina! We hope we can return one day!

Apartment rentals with outdoor seating

Top guest favorite
A spacious terrace is furnished with a wooden table and chairs, surrounded by greenery. The railing provides a view of the neighborhood, with buildings and trees visible in the background. Bright sunlight illuminates the area, creating a welcoming outdoor space.
Apartment in Castiglione della Pescaia
4.94 out of 5 average rating, 65 reviews

TERRACE APARTMENT CASTIGLIONE

KevinRating, 5 stars2 weeks ago
The stay in Letizia's apartment was just perfect! The apartment is very well equipped, nice and large and really offers everything you need. The balcony is a highlight – ideal for relaxing. The air conditioning also works perfectly, which made the stay particularly pleasant. The beach is only a 3-minute walk away, and the old town is easily reached in about 10 minutes on foot. Everything was great – thank you so much for the great place! I'd love to come back.
Guest favorite
A spacious bedroom features a large bed adorned with soft linens. Natural light enters through a window, complemented by warm lamplight. Stone walls and wooden beams add rustic charm. A dresser and side table provide functional decor, and framed images line the walls, enhancing the elegant atmosphere.
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Top guest favorite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino
4.9 out of 5 average rating, 359 reviews

Panoramic Country Suite Montalcino

BernhardRating, 5 stars3 days ago
We stayed at Aleksandra's in Montalcino in the heart of Brunello, a breathtakingly beautiful area, for a week. The large property is fantastic and with the tranquility and the view just the right thing to relax and unwind. An unforgettable experience for the whole family. This is how you imagine a Tuscan holiday. We highly recommend the place.
Top guest favorite
A spacious bedroom features a comfortable bed with a soft grey headboard and neutral bedding. A small dining area with a wooden table and two dishes is visible. A large mirror and a flat-screen TV are mounted on the wall, reflecting natural light from a nearby window.
Apartment in Sinalunga
4.99 out of 5 average rating, 275 reviews

Resort Panoramic view - Free parking

EnricoRating, 5 stars3 days ago
Charming living room, bedroom and patio with a view that is unparalleled in beauty and tranquility. Beautiful room, well-stocked, everything extremely well cared for in detail by a person - Elena, although we did not have the opportunity to meet - who puts love into providing an experience that is absolutely worth repeating. The common areas are also extremely well-kept and comfortable.
Guest favorite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello
4.97 out of 5 average rating, 153 reviews

Casa Bonari - a paradise for the eyes

KristopherRating, 5 stars3 weeks ago
This is Tuscany at its finest! Our stay at Casa Bonari was perfect. The villa inside was spacious, beautiful, comfortable, and wonderfully Italian. It was equipped with everything we needed. The exterior grounds were gorgeous and the views from the property in every direction were breathtaking. We made dinner and ate on the patio - it looked like a picture from a magazine. The villa is within easy walking distance of the charming Monticchiello which has a few excellent restaurants. We enjoyed strolling the picturesque streets and the incredible views of the countryside from the village. Our hostess, Valentina, was very gracious and helpful. We enjoyed meeting some of the friendly family members. They were so kind and left us with happy memories. We highly recommend Casa Bonari and hope to visit again.
Superhost
An outdoor courtyard is featured, equipped with a round table and four chairs, shaded by a large umbrella. A lounge chair is positioned beside the table, surrounded by greenery and stone walls that provide a cozy, private setting.
Apartment in Castiglione della Pescaia
4.78 out of 5 average rating, 50 reviews

Taste of the sea...

AndréRating, 5 stars9 months ago
A lovely apartment within walking distance of the beach and village. The outdoor space is not that large but large enough to sit comfortably. Inside it is much more spacious and very cozy and tastefully decorated by Angelo. Of all the comforts including a beautiful bathroom. Would go there again in a heartbeat and really recommended! André and Brigitte
Guest favorite
A crystal-clear swimming pool is surrounded by a well-maintained grassy area. Several sun loungers are positioned nearby, alongside a small table. Lush greenery and trees provide a natural backdrop, enhancing the serene setting. A distant building is partially visible beyond the foliage.
Apartment in Castiglione della Pescaia
4.87 out of 5 average rating, 46 reviews

Agriturismo Bandinelli #2 "Campini"

PRating, 5 stars2 weeks ago
We felt so comfortable between the fields in absolute peace. We were able to relax very well in the idyll. Everything is very well maintained and tastefully decorated inside and out. By car, you can also reach the pretty harbor town very quickly and can eat well and shop. David was always available for questions. We would definitely come back.
Superhost
A panoramic view of colorful rooftops leads to the sparkling blue sea, with hills in the background and a distinctive tower rising above the buildings. The landscape captures the charming coastal town and its vibrant architecture, set under a clear sky.
Apartment in Porto Santo Stefano
4.88 out of 5 average rating, 163 reviews

Far Horizons:Uniquely panoramic peaceful sea views

JacquelineRating, 5 stars2 weeks ago
We had a fantastic stay at Keith’s beautiful apartment. We were four adults and a baby and had plenty of room. The views are outstanding - even better than the pictures - and the street is quiet and within walking distance to everything you could want to see in Porto Santo Stefano. Keith was responsive, friendly, and flexible with check-in when we ended up arriving quite late. We couldn’t have asked for a better stay!

Condo rentals with outdoor seating

Top guest favorite
An aerial view showcases a historic building with a tiled roof, situated against a rocky cliff. A terrace with seating and a small table is visible, surrounded by greenery below, evoking a sense of tranquility and connection to nature.
Condo in Pitigliano
4.99 out of 5 average rating, 123 reviews

Le Antiche Viste - The Zen Terrace

DavideRating, 5 stars6 days ago
What can I say except that Beatrice and her husband deserve a 10 with honors. Fantastic location, they are very kind. Everything was perfect. Try their aperitif, which is not just an aperitif but much more
Top guest favorite
A spacious bedroom features warm brick walls and a wooden beamed ceiling. A large bed with a striped blanket is positioned next to a cozy seating area. A desk and chair setup is visible, along with a Smart TV mounted above, completing the functional space.
Condo in Torrenieri
4.97 out of 5 average rating, 241 reviews

[9 minutes from Montalcino] Elegant House Mafalda

AnthonyRating, 5 stars2 weeks ago
Marco’s place is away from the hustle and bustle of Siena very quietly comfortable and super clean. The view from the balcony alone is worth the night rate. Close to all the lovely sights in Val D’Orcia. In a very quaint town with locals who actually live here. Marco is very responsive and clearly explained everything to us. Must try the pizza at Pizza I’ll Vecchio…a hidden gem in Tuscany
Guest favorite
A spacious terrace features wooden furniture, including a table and chairs, set against a backdrop of a sunset illuminating the sky over the sea. Stone columns provide structural support, and a railing offers a clear view of the surrounding coastal landscape.
Condo in Porto Santo Stefano
4.89 out of 5 average rating, 149 reviews

Penthouse in Porto Santo Stefano

LizzieRating, 5 stars2 weeks ago
We had the most fantastic stay at Antonio’s as a couple with a young baby. Everything in the apartment is as it appears in pictures. If is so practical and perfect. Also, Antonio has really great furniture, no IKEA here. He set up a pack n play for the baby. The patio was the crown jewel and the view was stunning. In June the sun was high quickly and the patio received shade early on in the day. Bed was firm. kitchen small but efficient. Outdoor cooking was lovely. The apartment was stocked for cooking and even toiletries. AC in the bedroom but doors open provided plenty of fresh air to keep the apartment cool during the day. Walking into town with was easy, driving is too on weekdays. The apartment has an elevator to reach the top floor, but you do need to bring the bags up two flights outside from the street unless you have a small car that can reach the driveway. We would not hesitate to stay at Antonio’s again!
Top guest favorite
A rustic living area is showcased with exposed wooden beams and stone walls. A dining table is set with chairs nearby, alongside a cozy armchair. Light enters through a window, complementing the warm tones of the space. A fireplace and decorative artwork enhance the inviting atmosphere.
Condo in Manciano
4.95 out of 5 average rating, 105 reviews

The Maremma on a Terrace-House with a viewpoint and fireplace

IlyaRating, 5 stars1 month ago
It is a great place to stay and feel the quiet and peace of Tuscany! My family and I really enjoyed it. The apartment is really nice, with a unique style inside an ancient house. And without a doubt, it has one of the best views from the kitchen and terrace that I have ever seen!
Guest favorite
The image depicts a historic building with a prominent bell tower, characterized by its tall spire and intricate brickwork. A sky filled with clouds in various shades of blue and purple provides a serene backdrop, complementing the architectural details of the structure.
Condo in Grosseto
4.87 out of 5 average rating, 117 reviews

Characteristic old town A. & G.

RileyRating, 5 stars1 week ago
Filippo was the best host to have. He and his family are the most kind people I interacted with throughout my entire trip to Italy. The space itself is just as it is listed, everything worked perfectly, and we enjoyed our stay. I would highly recommend staying here. Being on the top floor of the complex gives a great view of the surorunding area and it was cool and breezy with the windows open. I could not have asked for a better experience and homebase for my travels.
Guest favorite
The spacious kitchen and living area features a central island counter with a wine bottle and glasses. Natural light floods the space through multiple windows, illuminating the dining table and a cozy seating area with a sofa. A rustic ceiling enhances the homey ambiance.
Condo in Pienza
4.91 out of 5 average rating, 99 reviews

Amazing view of Val d'Orcia Pienza

AnneRating, 5 stars1 month ago
Very comfortable accommodations and gorgeous property and views
Guest favorite
A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.
Condo in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
We can absolutely recommend it! Everything is as described in the text and seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information about the arrival and many great local tips, always with the corresponding links. For example, our arrival was delayed due to traffic to about 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where to park in Siena, how to get to Florence, ...)
Superhost
A charming exterior of the villa is displayed, featuring a pink stucco facade and green shutters. A tiled terrace is visible in front, surrounded by greenery. The view of the sea is unobstructed, and the inviting entrance door suggests easy access.
Condo in Porto Santo Stefano
4.88 out of 5 average rating, 203 reviews

Charming apartment with breathtaking sea views

IsabelleRating, 5 stars2 weeks ago
Matteo’s place has a really breathtaking view ! It’s also very quiet and peaceful. Also close to PSS via the shortcut. We had a wonderful time. Don’t miss a trip to Giglio !

Quick stats about vacation rentals with outdoor seating in Castiglione della Pescaia

  • Total rentals

    130 properties

  • Nightly prices starting at

    G$14,645 GYD before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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