Gaiole in Chianti Holiday Rentals from AU$77: 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 espresso maker. You can relax into your holiday with a garden and a library.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Gaiole in Chianti holiday rentals

A stone building with a yellow sign reading "b&b erioico".

1. L' Eroico

Gaiole in Chianti

Angela

includes taxes & fees

29 Aug - 30 Aug

A stone building with a garden in front.

2. Borgo Argenina

Gaiole in Chianti

Sabatino

includes taxes & fees

30 Aug - 31 Aug

A table set with various items including a book, glassware, and decorative objects against a stone wall backdrop.

3. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

Gaiole in Chianti

Mariah M.

includes taxes & fees

25 Sept - 26 Sept

A swimming pool with a colorful inflatable ring and a water fountain.

4. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

includes taxes & fees

2 Sept - 3 Sept

A dining area with a table and chairs, a sofa, and large windows with curtains.

5. 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

Gaiole in Chianti

includes taxes & fees

27 Sept - 28 Sept

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

6. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

includes taxes & fees

10 Sept - 11 Sept

A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

7. Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

Gaiole in chianti

includes taxes & fees

26 Sept - 27 Sept

An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

8. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

includes taxes & fees

30 Aug - 31 Aug

9. Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Gaiole in chianti

includes taxes & fees

11 Sept - 12 Sept

10. Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

Gaiole in chianti

includes taxes & fees

28 Sept - 29 Sept

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

11. Villa di Sotto

Castelnuovo Berardenga

Philippe

includes taxes & fees

21 Sept - 22 Sept

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

12. Mariani Bed & Breakfast

Castellina in Chianti

Chie

includes taxes & fees

2 Sept - 3 Sept

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

13. Residenzia del Sogno

Castellina in Chianti

Katherine

includes taxes & fees

2 Sept - 3 Sept

A villa with a swimming pool, outdoor seating, and a tennis court.

14. Villa Curina Resort

Castelnuovo Berardenga

Mary

includes taxes & fees

27 Sept - 28 Sept

A pool area with a water slide and a stage for performances.

15. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

includes taxes & fees

3 Sept - 4 Sept

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

16. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

includes taxes & fees

1 Sept - 2 Sept

A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Ravacciano

Alissia

includes taxes & fees

24 Sept - 25 Sept

A table with breakfast items and a view of rolling hills.

18. Chianti Village Morrocco

Barberino Tavarnelle

Chris

includes taxes & fees

7 Sept - 8 Sept

A rustic stone building with a courtyard.

19. Fullino Nero

Siena

Christian

includes taxes & fees

2 Sept - 3 Sept

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

20. Riserva di Fizzano Residence

Castellina in Chianti

Janet

includes taxes & fees

8 Sept - 9 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Great location, beautiful rooms, wonderful staff!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This is a very special Tuscan style hotel in the beautiful countryside surrounded by vineyards and olive groves. The staff were excellent, special mention goes to Elisa ,and the food was amazing. My only feedback, if you pay for a treatment the other spa facilities should be included. Also, the gym is very small but let's I wasn't there to train."

Poderi Arcangelo

8/10 Good

"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."

Castello di Tornano Wine Resort

8/10 Good

"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome but its a climb"

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, 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 favourite 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 depend 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 AU$77 per night. Entering your travel dates in the search wizard might find you 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 espresso maker. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 23 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti holiday rentals

1. L' Eroico

2. Borgo Argenina

3. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

4. Farmhouse in Chianti

5. 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

6. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

7. Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

8. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

9. Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

10. Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

11. Villa di Sotto

12. Mariani Bed & Breakfast

13. Residenzia del Sogno

14. Villa Curina Resort

15. Hu Norcenni Girasole Village

16. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

17. Domus il Palio B&B

18. Chianti Village Morrocco

19. Fullino Nero

20. Riserva di Fizzano Residence

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Borgo Scopeto Wine & Country Relais

Poderi Arcangelo

Villa Olmi Firenze

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Hu Firenze Camping In Town

Castello di Tornano Wine Resort

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Find out more about Gaiole in Chianti

Frequently asked questions

Go further with the Expedia app