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Featured Villas in Certaldo and around

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (92)
"Lovely large 4 bedroom house with spectacular views of San Gimignano. Really enjoyed our stay and highly recommend this rental. Everything was perfect including the pool. Alessandro "
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Luxury Villa in the Florentine hills
9.8 out of 10, Exceptional, (127)
"My wife and I chose this Villa based on the location as well as the pictures provided in the advertisement. The location was absolutely fabulous. My son and daughter in law joined us the first week, and all the excursions in the Tuscon region were within a hour to an hour and a half drive from the Villa. It was very convenient. Also there are a couple very small towns nearby where we did our grocery shopping as well as small specialty shops and restaurants. The Villa was very clean and had...
Luxury Villa in the Florentine hills
Tailored stay・Villa w/ heated pool, concierge service, 8 mile to Florence Center
10.0 out of 10, Exceptional, (94)
"Our group of 10 just checked out of the villa today. Five couples from the USA and we were all extremely pleased with our accommodations and time spent in the region of Impruneta. Our hostess, Caterina and her family were responsive to every question whether it was local restaurants, local tours of pottery, specific Florence Shopping options, parking or train schedules. We utilized almost every area of the Villa specifically the clean and refreshing swimming pool, ping pong table and well...
Tailored stay・Villa w/ heated pool, concierge service, 8 mile to Florence Center
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (79)
"This was our second villa rental in the San Gimignano area, our first at Alessandro's villa and it was amazing! Alessandro was very responsive and helpful from the moment we booked the year prior, until the day we checked out. We were a group of 6 adults and had plenty of room. The villa has every amenity you might need during your stay. At check in Alessandro provided us with helpful information about the surrounding area. The villa is in a beautiful setting surrounded by vineyards and olive...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Beautiful villa with private pool immersed in the Tuscan countryside
10.0 out of 10, Exceptional, (103)
"The property is an authentic Tuscan dream and the view is so stunning it is almost unreal. Francesca is an excellent host whose personal history with the house shines through in her attentiveness and care of her guests and their experience while visiting. 100% recommended."
Beautiful villa with private pool immersed in the Tuscan countryside
15th century barn fully renovated in a stylish style with gorgeous swimming pool
10.0 out of 10, Exceptional, (4)
"The renovated barn has been lovingly and tastefully transformed into a beautiful Tuscan villa—the perfect base for our family’s first visit to the area. The space is truly unique in all the ways it has incorporated modern design and amenities while preserving the rustic charm of the structure. The rooms and furnishings are comfortable, and the kitchen is a great place to prepare a meal with fresh local ingredients. The location was ideal for our itinerary, as we could easily visit Siena and San...
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Villa luna with pool and garden near the center of Siena
8.8 out of 10, Excellent, (25)
"Wonderful location. Loved the view, the pool, the outdoor bbq area"
Villa luna with pool and garden near the center of Siena
Vacation home L'Ulivo in Tuscany,
9.8 out of 10, Exceptional, (13)
"The house was amazing, we had the entire top floor of the house, which had large bedrooms, common area and kitchen. The entire place was very nice and was quiet, which made it easy to relax and end a nice holiday. The pool area is share with other renters in the area, but was not an issue during our stay. I would definitely stay here again."
Vacation home L'Ulivo in Tuscany,
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
New 2 bed villa with large panoramic pool 40min to beaches
10.0 out of 10, Exceptional, (33)
"My wife and I had a fantastic week at the villa, we are very grateful to Mrs Consuelo for the hospitality and everything she did for us, what a fantastic lady!!! A great thank you to Mr Marcello for the free wine and fresh salad from the allotment, again thank you very much from Antonio & Louise from London"
New 2 bed villa with large panoramic pool 40min to beaches
Casa Martina-Detached house, fenced garden and swimming pool for exclusive use!
9.4 out of 10, Exceptional, (8)
"The house is superb. The patio is covered and lit romantically. It offers insect repellent light. The pool is clean and shady during the day (chairs, not the pool itself). It is also fenced, as is the whole property, which helps if you travel with children or pets (dogs have their own outside bar installed). Rooms are spacious and have misquote nets which is extremely rare. They are also air conditioned. Kitchen is well equipped. The owners are extremely nice and welcoming. They will take care...
Casa Martina-Detached house, fenced garden and swimming pool for exclusive use!
Villa with private swimming pool in quiet area, private garden, panoramic views
10.0 out of 10, Exceptional, (7)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
9.8 out of 10, Exceptional, (25)
"Beautiful property and old world charm. Perfectly located and lovely hosts."
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
Villa with view and private pool
10.0 out of 10, Exceptional, (19)
"We thoroughly enjoyed our stay at the villa. It was relaxing and comfortable and well stocked. Gullia did an amazing job giving suggestions of places to go and things to do. We wish the pool would have been heated bc the weather was chilly during our stay but everything else was perfect."
Villa with view and private pool
Luxury Villa with large pool close to Florence
10.0 out of 10, Exceptional, (61)
"This villa is spectacular. Panoramic views are breathtaking. The villa is beautiful and perfectly maintained. The pool was great. Best of all the hosts live there as well. They are wonderful people. So helpful and friendly. Fonsy is a Fantastic chef who prepared outstanding meals for our family. Our stay was perfect. I had dreamed of renting a villa for many years. This was even better than I could have dreamed. Definitely recommend Il Faeto to live your Tuscan dream. Our three...
Luxury Villa with large pool close to Florence
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Villa Feudo, incredible villa with private pool and park, located in Cerbaia, in the Tuscan coun...
10.0 out of 10, Exceptional, (6)
"Great location, close to Florence. Comfortable beds."
Villa Feudo, incredible villa with private pool and park, located in Cerbaia, in the Tuscan coun...
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
9.6 out of 10, Exceptional, (16)
"We enjoyed a delightful two weeks staying at Villa Il Borrachio in September. Apartment Azalea is spacious, well equipped and set on two floors. The two bedrooms on the first floor have double beds and en-suites whilst the bedroom on the ground floor has two single beds with a bathroom located on the other side of the kitchen/dining area. There is a wonderful view from the living room of the countryside with San Gimignano in the distance. The wi-fi was good and with our laptop plus hdmi cable we...
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
9.0 out of 10, Wonderful, (2)
"Très belle maison et cadre agréable "
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
Villa Orsini Peccioli - Historic villa with swimming pool for exclusive use
10.0 out of 10, Exceptional, (4)
"Roberta was amazing. Villa was spotless and we appreciated all the little touches she provided. Beds were comfortable, kitchen well equipped and the pizza oven was so much fun. Pool was perfect temperature and amazing sunsets with a cocktail finished a perfect evening. Easy to walk or drive to town. "
Villa Orsini Peccioli - Historic villa with swimming pool for exclusive use
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Other property types in Certaldo

Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1198)
"The shuttle was extremely useful. "
The price is €108
includes taxes & fees
3 Oct - 4 Oct
Hu Firenze Camping In Town
Forte16
9.6 out of 10, Exceptional, (739)
"Forte16 had everything we could possibly want from a comfortable and well-equipped hotel. It was well placed for restaurants, groceries and ice cream and was only a short walk from the bustling streets of central Florence. Efficient bus links were conveniently placed on the street corner. After long, busy days exploring, the thermal spa pool was just what we needed. The air-conditioned rooms enabled us sleep soundly and the kitchenette enabled us to keep drinks and fruit snacks cool in the...
The price is €195
includes taxes & fees
27 Oct - 28 Oct
Forte16
PopArtment
9.0 out of 10, Wonderful, (675)
"Great location with huge rooms and super close to the train station! "
The price is €190
includes taxes & fees
29 Sept - 30 Sept
PopArtment
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Certaldo cost?
You can expect to pay between and per night for a villa in Certaldo. Whatever your budget, a fantastic escape is just a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Certaldo?
You can choose from 1556 villas in Certaldo. Whether you’re holidaying with the family or organising a weekend escape with your besties, Expedia will help you find the perfect space for your squad.
Why book your villa in Certaldo with Expedia?
Expedia makes it a cinch to find your dream villa in Certaldo. Taking the kids on holiday? Use our handy filters to search for stays with a kitchen or a pool. If you have a fixed budget, click on how much you’d like to spend and your preferred star rating. We’ll help you find the perfect pad that matches your taste and style.
How can I find cheap villas in Certaldo?
Expedia is here to help you easily source cheap villas in Certaldo. Use the filter tool to select amenities, star rating and budget to refine your search and find an ideal stay in a few quick keystrokes.
What is there to do near my villa in Certaldo?
The ideal travel accessory is a well-thought-out travel plan. Palazzo Pretorio is a good place to start your adventures in Certaldo.