Gaiole in Chianti Holiday Rentals from €65: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano : This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

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Holiday Rentals in Gaiole in Chianti

Relax in a cozy retreat with a neatly made bed, bedside table, and modern bathroom amenities.

"The whole family is very happy. Bus stop close by. Easy to get in to Florence city center. Nice pool area. Good restaurant. "

includes taxes & fees

10 Aug - 11 Aug

Enjoy a sea view from the covered porch of this cabin, which features a dining area with a table and chairs.

"Great friendly fun camp site"

includes taxes & fees

2 Aug - 3 Aug

Enjoy a selection of beverages and sweet treats in our bar area, featuring a variety of bottles, glasses, and a display case of pastries.

"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."

Escape to a serene villa surrounded by lush greenery and a tranquil pool.

"Beautiful place!! For sure I will come back!! "

includes taxes & fees

3 Aug - 4 Aug

Surrounded by lush greenery and vineyards, this traditional complex offers a tranquil setting with a swimming pool and sun loungers.

"We enjoyed the scenery and service! Clean and comfortable. "

Relax by the serene pool surrounded by lush greenery and palm trees.

"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "

includes taxes & fees

25 Aug - 26 Aug

Relax by the serene pool surrounded by lush greenery and lavender, with comfortable lounge chairs and umbrellas.

"Anna is very attentive and really helpful. She really does want you to have the best time and experience in her home. The location is good as long as you don’t mind a little drive. The house and grounds are STUNNING! We loved our stay and would go back. The weather wasn’t great when we went but we still utilised the pool and hot tub when possible. Our children also loved the place and we all had fun regardless of weather. Thanks Anna"

Relax by the serene pool surrounded by lush greenery and well-maintained hedges.

"Safe, great proximity to Siena without being too close, nice pool."

Relax in the stylish lobby with comfortable sofas, a glass coffee table, and a beautiful view of the surrounding area.

"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."

includes taxes & fees

19 Aug - 20 Aug

Step into Il Battistero, a charming coffee shop with a welcoming atmosphere and a variety of beverages.

"Excellent staffing, nice facility and great location"

includes taxes & fees

5 Aug - 6 Aug

Enjoy a compact kitchen with microwave, oven, and dishwasher, plus a dining area and cozy living space.

"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."

Relax by the pool surrounded by lounge chairs and lush greenery.

"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "

Relax by the pool surrounded by a white picket fence.

"Nothing wrong here! Fantastic, professional staff that took care of all our needs and always went the extra mile. Fantastic chef with great food and lovely “can help” attitude. Prestine pool! Would book again"

includes taxes & fees

24 Aug - 25 Aug

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."

Relax by the serene pool surrounded by lush greenery and a charming stone building.

"Our host Maurizio, added quite a few extra layers of enjoyment to our stay. A brilliant host who went above and beyond to make our holiday truely memorable! We have invited him to come stay with us when he visits Australia. As for the farm house it’s self, an amazing experience to live like a true Italian. If you want to experience country life, I recommend La Rustica! Thank you Maurizio and Simonetta. ❤️"

Relax by the serene pool surrounded by lush greenery and a tranquil atmosphere.

"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"

Relax in a charming outdoor space surrounded by lush greenery and a stone wall.

"Quaint, authentic and comfy. "

Enjoy dining al fresco on this scenic outdoor terrace with a table set amidst a serene natural backdrop.

"Very clean and comfortable accommodations. Beautiful view of the countryside!"

includes taxes & fees

3 Aug - 4 Aug

Enjoy dining al fresco amidst lush greenery and warm ambiance.

"The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again "

includes taxes & fees

20 Aug - 21 Aug

Relax by the serene pool surrounded by lush greenery and rolling hills.

"Perfect location for a family reunion with our adult children and their partners. We had a wonderful time."

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Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"Very well maintained, renovated 19th century building. Close to all attractions, while still easily accessible by car, very close to the pedestrian zone of the old town. Parking is not free, but reasonable (15 Eur/day in the hotels garage). There is no elevator, so you will need to climb some stairs (on the plus side they are all marble stairs). The room was a good size (for 3 adults), tha bathroom is smaller but very clean and nice. It was quiet and air conditioning was working well. We had a good sleep, the blinds can be shut completely, good if you like to sleep longer. The two large mirrors made the room to feel even bigger. Overall, it is a better 3-star hotel. Only drawback for some may be the lack of elevator."

Hotel Borgo di Cortefreda Relais

10/10 Excellent

"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."

La Certosa di Pontignano

10/10 Excellent

"Our stay at La Certosa di Pontignano was a truly memorable experience. The historic charm of the property combined with the serene Tuscan landscape creates a magical and peaceful atmosphere that’s hard to match. The rooms were comfortable, the grounds beautifully maintained, and the staff welcoming and attentive. While we did encounter a small issue during our stay, it was addressed promptly and resolved to our complete satisfaction, which we greatly appreciated. The overall experience far outweighed this minor hiccup. The historical significance of the location adds a special depth to the visit—walking through centuries-old cloisters and gardens while enjoying the beauty of Tuscany is something we won’t forget. We would gladly return and highly recommend it to anyone looking for a unique and tranquil retreat."

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gaiole in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaiole in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaiole in Chianti holiday rentals we have selected for you start as low as €65 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gaiole in Chianti rentals

At Expedia, we put the best Gaiole in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Gaiole in Chianti?

Yes, there are holiday rentals close to the most popular sights in Gaiole in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. The spas and wineries are several reasons why visitors like Gaiole in Chianti. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 49 Expedia holiday rentals, you're guaranteed to find just the right place for your Gaiole in Chianti stay.

What’s there to see and do in Gaiole in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Terme Antica Querciolaia. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

What’s a holiday rental in Gaiole in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaiole in Chianti. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Holiday Rentals in Gaiole in Chianti

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Holiday Rentals in Gaiole in Chianti

Hu Firenze Camping In Town

Hu Norcenni Girasole Village

Camping Boschetto Di Piemma

Relais Villa Olmo

Bosco della Spina

Camping Village Il Poggetto

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Camping Siena Colleverde

ApartHotel Anghel

Il Battistero Siena - Residenza d'Epoca

Regis Condo

Villa in Montalcino, exclusive for you, stunning view!!!

Chianti Village Morrocco

Villa San Filippo

17th century farmhouse with private pool and Wi-Fi and air conditioning

Villa Il Palagio

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Tuscasì Aparthotel

Made for gathering together, leave the rest to us - Villa 20 minutes to Florence

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

Hotel Athena

Palazzo Ravizza

Hotel Borgo di Cortefreda Relais

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hu Firenze Camping In Town

La Certosa di Pontignano

NH Siena

Find out more about Gaiole in Chianti

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