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Villa vacation rentals in Certaldo

Find and book unique villas on Airbnb

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Popular amenities for Certaldo villa rentals

Private villa rentals

Superhost
A scenic pathway leads through a lush green landscape, bordered by flowering lavender and vibrant red blooms. The pathway is flanked by neatly trimmed trees, creating a serene and inviting atmosphere that connects the property to the natural surroundings.
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Superhost
The spacious living room features a decorative ceiling with ornate detailing. Various art pieces adorn the walls, while elegant furnishings are arranged throughout. Natural light streams in through several windows, creating a bright and welcoming environment accented by carefully curated decor.
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MiltonRating, 5 stars7 months ago
Fantastic all around experience. Thank you Elio and team 🙏🙏
Superhost
The villa features a classic architectural design with a decorative roofline. A wrought iron balcony extends across the front, complemented by several large windows. The entrance is framed by greenery, with a gravel pathway leading up to the building.
Villa in Marlia
4.87 out of 5 average rating, 23 reviews

Charming Villa -private swimming pool -16 people.

LauraRating, 5 stars9 months ago
Beautiful house in a stunning location. Pool was great. Perfect for a large family. Owners were very helpful and available when needed. Rooms were hot overnight but this is expected in peak summer in Italy.
Guest favorite
A well-kept garden area is visible, featuring a stone table surrounded by lush greenery. The structure is framed by mature trees, providing shade and a sense of tranquility. Arched windows of the villa can be seen in the background, offering glimpses of the interior.
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Superhost
A two-story villa is surrounded by a lush green lawn and tall trees. Two lounge chairs are positioned on the grass, inviting relaxation. The building is made of stone and wood, featuring balconies that overlook the landscape of vineyards and Tuscan hills.
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars5 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Guest favorite
The villa is surrounded by a lush garden, featuring well-maintained greenery and colorful flower beds. Two large umbrellas provide shade over the outdoor seating area, and a swing hangs from a sturdy tree, inviting relaxation in the peaceful setting.
Villa in Sarteano
5 out of 5 average rating, 13 reviews

Villa "La Civetta" with swimming pool, sauna and jacuzzi

BrynRating, 5 stars7 months ago
Lovely modern home in a beautiful, quiet town in southern Tuscany. We had a wonderful 8 days there with our 6 year old son.
Superhost
A charming stone farmhouse is set against a clear blue sky, framed by lush greenery. In the foreground, a private saltwater pool reflects the vibrant flowers in planters on the wooden deck, creating a serene outdoor scene ideal for relaxation.
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.
Guest favorite
A stone villa is illustrated with large windows and an expansive terrace. A well-manicured lawn stretches to a sparkling pool, complemented by sun loungers. Lush greenery surrounds the area, enhancing the serene outdoor space.
Villa in Gaiole in Chianti
5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

VaughanRating, 5 stars6 months ago
A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.

Luxury villa rentals

Top guest favorite
An aerial view captures the villa’s expansive layout, featuring a private pool surrounded by lounge chairs. Lush greenery and cypress trees border the property, while terracotta roofs and open balconies contribute to the charming Tuscan landscape.
Villa in Montecucco
4.9 out of 5 average rating, 39 reviews

Villa Angiolina

ErinRating, 5 stars6 months ago
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!
Guest favorite
Villa in Casale
4.96 out of 5 average rating, 24 reviews

Villa with pool in chianti Rufina area 13 sleeps

AnnaRating, 5 stars1 week ago
The house was amazing, perfect fit for our group of 10 people. The main house as well as the additional apartment were very clean, well equipped with everything you need and the highlight was the pool and jacuzzi. Great place to calm down and have private space with some friends or a big family. The check-in was easy and the lady was very friendly, had some suggestions for our stay and is professional. The property was clean, cute tuscany decorations of the rooms and all in all it felt like home.
Top guest favorite
A welcoming living area is characterized by elegant furniture, including a pair of intricately designed chairs and a spacious couch. A decorative coffee table sits in the center, surrounded by soft natural light from the windows, and a vintage chandelier hangs above.
Villa in Rignano sull'Arno
5 out of 5 average rating, 10 reviews

villa "La Fonticina"

Salvador EsquedaRating, 5 stars4 days ago
Our stay at this beautiful Tuscany villa was truly unforgettable. The home perfectly blends charming, traditional Tuscan character with all the modern amenities we could possibly need. From the moment we arrived, we were enchanted by the authentic details — rustic beams, stone walls, and stunning countryside views — all while enjoying updated comforts like a fully equipped kitchen, high-speed internet, and luxurious bathrooms. It was the perfect balance of old-world charm and contemporary convenience. We couldn’t have asked for a better place to experience the magic of Tuscany. Highly recommend!
Superhost
The image depicts the exterior of a villa surrounded by lush green hedges and shrubs. A spacious terrace area is visible, with a tiled pathway leading towards the entrance. Upper floor balconies are adorned with decorative railings, enhancing the inviting look of the property.
Villa in Lucca
4.75 out of 5 average rating, 64 reviews

VILLA BIANCA AC BIG POOL WIFI

JessicaRating, 5 stars2 months ago
The villa is gorgeous scenic experience with views of the Tuscan hills. We came in Winter so we couldn’t use the lovely pool but enjoyed a wine tasting just up the street at Tenuta Maria Teresa. The rooms were comfortable, spacious, and we loved congregating in the living room to play games. We cooked meals in the kitchen and had what we needed. It was very private and tranquil location 12 minutes from Lucca. The hosts were friendly, communicative, and worked with us easily on check in and out times even letting us arrive early. It is typical in Italy to pay for heat consumption, came out to 226 euro for three days even when turning it low when gone for the day so just something to keep in mind as it is a large villa. Overall, a lovely experience and highly recommend the location. We’d come back.
Guest favorite
The villa is set on a hillside, surrounded by lush olive groves and cypress trees. Its traditional architecture features a terracotta roof and stone walls. Outdoor seating areas invite relaxation, while pathways lead through well-kept gardens that reflect the area's natural beauty.
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 21 reviews

Villa l'elsa beautiful country home with view - vi

MarcelaRating, 5 stars1 week ago
The house is amazing and the exterior is beautiful
Superhost
The expansive garden features well-maintained grass and elegant trees casting shadows on the ground. In the background, the villa's rustic brick facade complements the natural surroundings, while additional greenery and an open sky create a serene atmosphere.
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars36 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Superhost
The exterior of Villa Ama Dei is highlighted by a pastel-colored façade set against the lush Tuscan hills. A private swimming pool, surrounded by sun loungers, is framed by neatly arranged flower beds, while outdoor seating invites relaxation amidst the greenery.
Villa in Valdottavo
4.86 out of 5 average rating, 28 reviews

[POOL] - Beautiful Villa in Tuscany Countryside

CasparRating, 5 stars9 months ago
Very nice place with everything you need for a successful vacation. The kitchen and especially outdoor kitchen were well equipped to easily cook nice dinners for a bigger group. The pool was very nice. The house was clean and the bathrooms looked completely renovated. The best part was the hospitality of the owners. Very welcoming people that know the answer to all your questions about the area. Would recommend!
Top guest favorite
An outdoor pool area is framed by an archway, featuring a clear blue pool surrounded by lounge chairs. Tall cypress trees and lush greenery rise in the background, complementing the serene, natural landscape.
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

Villa rentals with a pool

Guest favorite
An aerial view showcases a modern villa surrounded by lush greenery, featuring a private infinity pool. Lounge chairs are positioned beside the pool, and the outdoor dining area is elegantly set on a spacious terrace, enhancing the outdoor living experience.
Villa in Palaia
5 out of 5 average rating, 9 reviews

Villa La Gemma

DeryaRating, 5 stars7 months ago
The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!
Guest favorite
Villa in Rosignano Marittimo
4.92 out of 5 average rating, 25 reviews

Villa Castiglioncello - access to the private sea

JürgRating, 5 stars7 months ago
House, location: right by the sea, fantastic views, spectacular sunsets, large house with special architecture offers plenty of space and privacy, ideal for a large family. Various garden terrace areas. Everything very well maintained and well equipped. Camilla is a very warm and competent host. We will be happy to come back!
Guest favorite
The exterior of the villa showcases a brick façade supported by wooden columns. A well-maintained lawn extends alongside the building, bordered by a rustic wooden fence. The serene landscape in the background highlights trees and open fields under a clear blue sky.
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars2 weeks ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Villa in Petrognano
4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars7 months ago
I have so much positive to say about this place! Despite what some reviews mention about the drive, it's absolutely worth it. There's a small restaurant just 2-3 minutes away, easy access to the city, and you're only about an hour from Pisa and some beaches. The house was perfect—everything well thought out and worth every penny. The pool was amazing, and the host was very responsive. If you're visiting in autumn or spring, bring warm clothes for the chilly evenings. We were sad to leave, and I can't wait to come back to this dreamy property!
Superhost
Villa in Capannori
4.96 out of 5 average rating, 23 reviews

Luxury Tuscany Villa on the hill with private pool

JanetRating, 5 stars2 weeks ago
This villa was something out of a dream. Stefania was so lovely and wonderful with recommendations and booking us a rez at a fantastic local gem of a restaurant. The views were incredible and the atmosphere was so relaxing. The villa itself was cozy and inviting. The outside seating area was well used by us for nightcaps, dinner and conversations about falling in love with Tuscany and all it's amazing nooks and crannies. We wanted a picturesque and home-like central base for our 10 day adventure in Italy and we're delighted with the accommodations that really was like something out of a movie. Lucca was only a short drive away and offered the best grocery store-Esselunga! Thank you Stefania for your warm generosity, kindness and suggestions. This was a birthday trip that we will never forget and cemented our longing to return soon!
Guest favorite
A well-maintained garden area features two large umbrellas providing shade over lounge chairs. A view of the villa is visible in the background, along with a grassy expanse leading to a pool area, bordered by neatly trimmed hedges and trees.
Villa in Camaiore
4.85 out of 5 average rating, 27 reviews

Villa "I Nespoli" with above-ground pool

MarcoRating, 5 stars8 months ago
We had a wonderful week at Vincenzo's house. We were 2 families with children (5 total). The spaces in the house were perfect to accommodate everyone. The location, a 15-minute drive from the beaches of Lido di Camaiore and 35 minutes from beautiful Lucca, turned out to be perfect. Away from the chaos, surrounded by greenery and tranquility. Vincenzo is also a super host! Friendly and helpful. Absolutely recommended.
Superhost
A two-story house is visible through an open gate, framed by lush greenery. A spacious garden surrounds the property, providing a serene outdoor setting. Soft sunlight filters through the trees, highlighting the inviting exterior of the home and the covered patio area beneath.
Villa in Camaiore
4.85 out of 5 average rating, 27 reviews

Piccola Casa with pool

FaranakRating, 5 stars8 months ago
Amazing place to chill out and enjoy the nature. The pool was amazing and the house was very clean. We had an excellent time there, Thank you Anto❤️
Top guest favorite
An aerial view of the private villa is shown, surrounded by lush greenery and rolling Tuscan hills. The semi-Olympic pool is prominently featured, alongside the pool house, providing a serene backdrop for relaxation and recreation.
Villa in Montaione
4.95 out of 5 average rating, 22 reviews

Private Villa with semi-Olympic pool and Tennis

SuzanneRating, 5 stars6 months ago
Francesca’s home was beautiful and in a breathtaking, peaceful location. There is a short, beautiful walk with Mountain View’s and olive groves to an incredible pool and pool house. She was incredibly helpful in helping us not only access the home, but also in providing us local recommendations. The meal that Ettore prepared for us was one of the highlights of our trip.

Destinations to explore