Gaiole in Chianti Vacation Rentals from CA $75: Short-Term Rentals for 2026

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

Borgo Argiano : You might want to consider this vacation home rental near Gaiole in Chianti, which is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library.

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Our top choices for Gaiole in Chianti vacation rentals

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

1. L' Eroico

Gaiole in Chianti

Angela

CA $249 total

includes taxes & fees

Oct 9 - Oct 10

A stone building with a garden in front.

2. Borgo Argenina

Gaiole in Chianti

Tatevik

CA $282 total

includes taxes & fees

Sep 28 - Sep 29

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

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

Gaiole in Chianti

CA $2,631 total

includes taxes & fees

Oct 12 - Oct 13

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

4. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

CA $806 total

includes taxes & fees

Sep 30 - Oct 1

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

5. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

CA $2,358 total

includes taxes & fees

Oct 6 - Oct 7

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

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

Gaiole in Chianti

Mariah M.

CA $425 total

includes taxes & fees

Oct 5 - Oct 6

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

CA $578 total

includes taxes & fees

Oct 15 - Oct 16

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

CA $1,846 total

includes taxes & fees

Oct 6 - Oct 7

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

Gaiole in chianti

CA $586 total

includes taxes & fees

Oct 15 - Oct 16

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

Gaiole in chianti

CA $804 total

includes taxes & fees

Oct 12 - Oct 13

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

CA $308 total

includes taxes & fees

Oct 1 - Oct 2

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

12. Villa Curina Resort

Castelnuovo Berardenga

Deanna

CA $240 total

includes taxes & fees

Oct 4 - Oct 5

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

13. Riserva di Fizzano Residence

Castellina in Chianti

Janet

CA $300 total

includes taxes & fees

Sep 29 - Sep 30

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

14. Chianti Village Morrocco

Tavarnelle Val di Pesa

Winonah

CA $117 total

includes taxes & fees

Oct 12 - Oct 13

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

15. Terre di Baccio

Greve in Chianti

Gage

CA $874 total

includes taxes & fees

Sep 28 - Sep 29

An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

16. Ca' Bianca Tuscany Relais

Siena

Talha

CA $505 total

includes taxes & fees

Sep 28 - Sep 29

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

17. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

CA $236 total

includes taxes & fees

Sep 28 - Sep 29

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

18. Mariani Bed & Breakfast

Castellina in Chianti

Frank

CA $128 total

includes taxes & fees

Oct 8 - Oct 9

A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

19. Villa Rosa Panzano

Greve in Chianti

Allison

CA $200 total

includes taxes & fees

Oct 4 - Oct 5

A bathroom with a window view of a historic building and a tiled roof.

20. Siena Vip

Siena City Centre

Luis

CA $175 total

includes taxes & fees

Oct 21 - Oct 22

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Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Beautiful property close to San Gimignano historic center. Loved having option to have all meals here. Breakfast was way more expensive than other hotels so just had breakfast in town. But other meals were reasonably priced. If they would step up their game a bit (more pillows, seating in rooms, provide wine glasses and opener, cozy it up a bit with amenities), they could easily be a 4 star because the property itself is certainly 4 star."

Fattoria di Vegi

10/10 Excellent

"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"

Villa Pitiana

10/10 Excellent

"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gaiole in Chianti vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaiole in Chianti vacation rentals we have selected for you start as low as CA $75 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 vacation 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 vacation.

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 vacation rentals in Gaiole in Chianti?

Yes, we have vacation rentals close to the most popular attractions in Gaiole in Chianti, or you can choose a more secluded option if you're looking for relaxation. 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 vacation rentals that Gaiole in Chianti has to offer?

Borgo Argiano: You might want to consider this vacation home rental near Gaiole in Chianti, which is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 20 Expedia vacation rentals, you're sure 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 vacation rental in Gaiole in Chianti like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Gaiole in Chianti. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Gaiole in Chianti vacation rentals

1. L' Eroico

2. Borgo Argenina

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

4. Farmhouse in Chianti

5. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

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

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 Erborista' with Mountain View, Shared Garden and Wi-Fi

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

11. Villa di Sotto

12. Villa Curina Resort

13. Riserva di Fizzano Residence

14. Chianti Village Morrocco

15. Terre di Baccio

16. Ca' Bianca Tuscany Relais

17. Relais Villa Belpoggio - Residenza d'Epoca

18. Mariani Bed & Breakfast

19. Villa Rosa Panzano

20. Siena Vip

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

La Certosa di Pontignano

Hotel Athena

Hotel Casolare Le Terre Rosse

Fattoria di Vegi

Villa Pitiana

Radisson Blu Hotel, Florence

Hu Firenze Camping In Town

Find out more about Gaiole in Chianti

Frequently asked questions

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