Holiday houses in Pillo

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pillo

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Farm stay in San Gimignano

4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

Top Guest favourite

Apartment in Carmignano

4.96 out of 5 average rating, 197 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

Guest favourite

Condo in Gambassi Terme

4.87 out of 5 average rating, 45 reviews

Sunset_ by_ Bina

Sunset_ by_ Bina è un posto adatto a chi vuole rilassarsi completamente e fare un'esperienza unica nelle campagne del Chianti Toscano. Siamo completamente circondati da colline, uliveti e vigneti con un panorama mozzafiato. Nella mia casa puoi visualizzare l' alba e il tramonto tutti i giorni. A pochi km dal famoso borgo di San Gimignano, Volterra, Certaldo. Da qui potrai raggiungere facilmente non solo il cuore del Rinascimento, Firenze, ma anche città rinomate come Siena, Lucca, Pisa.

Superhost

Apartment in Gambassi Terme

5 out of 5 average rating, 5 reviews

Podere Boscone 3

Typical Tuscan farmhouse surrounded by nature. Surrounded by 42 hectares of vineyards and olive trees. The apartment located on the ground floor has an independent entrance. The entire complex is surrounded by a garden with a relaxation area created under an ancient oak tree, perfect for enjoying the Tuscan panorama. The farm also offers a seasonal swimming pool and free Wi-Fi. The main tourist areas (Florence, San Gimignano, Volterra, Siena) are easily reachable from the structure.

Guest favourite

Apartment in Gambassi Terme

4.89 out of 5 average rating, 44 reviews

Casa dell'Oriolo

Charming two-room apartment in the historic center of Gambassi Terme, a typical village located in the heart of the Tuscan countryside, between Florence and Siena. The apartment overlooks the town's central square, where there are bars, tobacconists, grocery stores and a bus stop. Free municipal parking is about 200 meters from the accommodation, one of which is equipped with electric charging stations. The historic municipal park and the renowned spa are within walking distance.

Guest favourite

Home in Montaione

4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Guest favourite

Condo in San Gimignano

4.93 out of 5 average rating, 118 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Guest favourite

Villa in Gambassi Terme

5 out of 5 average rating, 6 reviews

Villa Oliva w/pool+ ensuite - Pillo Holiday Villas

Welcome to VILLA OLIVA, a beautiful structure equipped with every comfort and an amazing swimming pool for exclusive use ready to brighten your summer days, between visiting a famous city and a stop in one of the many cellars located in Tuscany. Here you will feel at home, with large outdoor spaces where you can relax, play sports or go for a walk without forgetting the comfort of the 5 bedrooms each with a private bathroom!

Guest favourite

Farm stay in Simignano

4.89 out of 5 average rating, 198 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favourite

Home in Barberino Tavarnelle

4.91 out of 5 average rating, 144 reviews

La Casa di Nada - Suite

From every window of my home there are wonderful views of the Tuscan hills, a charm that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room I have a beautiful fireplace all for you. A practical laundry completes this refuge in the Heart of Chianti

Superhost

Villa in Gambassi Terme

4.85 out of 5 average rating, 152 reviews

Il Leccio - Tuscany home near San Gimignano

Tuscan farmhouse with beamed ceilings and large living area with fireplace. 3 bedrooms, 2 bathrooms and an outdoor area for lunches and dinners in the company. Hilly and windy landscape with panoramic views of the Tuscan countryside. 12 km from San Gimignano, 30 from Volterra, 30 from Siena and 2 km from the medieval village of Certaldo Alto.

Top Guest favourite

Apartment in Certaldo

4.97 out of 5 average rating, 112 reviews

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Pillo holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pillo

Guest favourite

Condo in Gambassi Terme

5 out of 5 average rating, 25 reviews

Bellavista Via Francigena Gambassi Terme

FabianRating, 5 stars3 days ago

Silvia's was exactly what I needed for the night. the bed was comfy, the facilities good. Highly recommended.

Guest favourite

Apartment in Gambassi Terme

4.92 out of 5 average rating, 150 reviews

La Cisterna Apartment - Gambassi Terme

ChrisRating, 5 stars1 week ago

Giacomo was very friendly and responsive

Top Guest favourite

Farm stay in Lastra a Signa

5 out of 5 average rating, 50 reviews

Authentic Farmhouse Apartment

MikeRating, 5 stars3 days ago

Tenuta Barosi is a beautiful location overlooking rural Florence. It is located just 25 minutes outside of Florence and easy to get to. The farmhouse has a number of apartments, and ours was Comiso. Cristina was extremely helpful with our check in, as we arrived very late. It is very easy to self check in. The pool overlooks a small valley with beautiful scenery of farms and vineyards. Highly recommend staying at Tenuta Barosi!

Superhost

Villa in Lucca

4.91 out of 5 average rating, 23 reviews

Villa Lina, Luxury Farmhouse with Pool and Amazing

BrookeRating, 5 stars1 month ago

Villa Lina was even more beautiful than the pictures showed. The house was clean, had new and comfortable bedding, had plenty of space for our family, and the view was outstanding. The place is very private, high up on the hill, but with the instructions from our host we had no trouble finding it, even in the dark. The driveway is about 1/4 mile, steep, with parts of it gravel, and has several sharp turns, but we made it no problem with the small jeep we rented (without 4WD). Just take it slow. It is about a 15 minute drive back down to the town center of Lucca and the train station and 10 minutes to a grocery store. The back roads are very narrow until you get to a main road so use caution and we were lucky enough that others backed up for us when we met on the narrow spots. The view and seclusion were well worth the drive up for us. If you want an amazing view of the Tuscan countryside, but also a short drive to a neat town and a train station, Villa Lina is a great choice!

Top Guest favourite

Villa in Gambassi Terme

5 out of 5 average rating, 14 reviews

Villa Boscone By MMega

CaileyRating, 5 stars1 week ago

Stunning and spectacular. Just two words to describe this beautiful place. The grounds are amazing and served as the beautiful backdrop for our wedding that kept all of our guests on site. The pool already is perfect for entertaining everyone, while there is also a lovely amount of outdoor seating areas for everyone to enjoy. The hosts were excellent and very friendly and responsive to anything we needed. Would stay here again and again!

Top Guest favourite

Condo in Castelfiorentino

5 out of 5 average rating, 7 reviews

Casa al Profeti

AdeleRating, 5 stars1 week ago

We had a great stay at Maurizio’s place! The apartment was clean, nicely furnished, and the kitchen was very well equipped. Maurizio gave us great tips for local trips and activities, which really made our stay special. The only downside was that the street outside could be a bit noisy at times, but overall it didn’t bother us much. This Airbnb is a great base for visiting Florence, Siena, and Pisa — either by car or by train. The historic towns of San Gimignano and Certaldo are also nearby, making it perfect for exploring Tuscany. Thanks again, Maurizio — we’d be happy to come back!

Home in Gambassi Terme

4.73 out of 5 average rating, 70 reviews

Authentic among stones and bricks

AnnaRating, 5 starstoday

We will consider it for the next times in the area! It is a great space to relax thanks to the well-kept furniture and the rustic style of the house, it will be the base for relaxation and sleeping, for eating we will try the restaurants in the area. A 5-star rating for cleanliness. Thanks and see you next time!

Cottage in San Gimignano

4.84 out of 5 average rating, 207 reviews

Countryside Cottage With View - Le Rondini apt

PeterRating, 5 stars3 weeks ago

A fabulous place in an amazing location. We sat in the garden everyday for breakfast looking at the beautiful views of Tuscany and San Gimignano. Marco was very helpful when we needed to contact him. The kitchen has all you need for 2 people if you want cook, but doesn’t have an oven just a combi microwave. Fridge Freezer was great for wine beer ice etc with plenty of space. Bathroom and shower also very good!

Show all

Holiday houses in Pillo

Top-rated holiday rentals in Pillo

Holiday rentals for every style

Popular amenities for Pillo holiday rentals

Other great holiday rentals in Pillo

Destinations to explore