Gaiole in Chianti Vacation Rentals from ￥9,129: Search Short-Term Rentals

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

Borgo Argiano : Visitors like this Gaiole in Chianti vacation home rental. It 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 an espresso maker. 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

1. L' Eroico

Gaiole in Chianti

Angela

￥27,904 total

includes taxes & fees

Aug 24 - Aug 25

2. Borgo Argenina

Gaiole in Chianti

Sabatino

￥47,356 total

includes taxes & fees

Aug 23 - Aug 24

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

Gaiole in Chianti

Mariah M.

￥50,507 total

includes taxes & fees

Sep 1 - Sep 2

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.

￥103,042 total

includes taxes & fees

Sep 1 - Sep 2

5. Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi

Gaiole in Chianti

￥348,950 total

includes taxes & fees

Aug 31 - Sep 1

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

Gaiole in Chianti

Bernard K.

￥253,275 total

includes taxes & fees

Aug 22 - Aug 23

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

Gaiole in chianti

￥63,682 total

includes taxes & fees

Sep 13 - Sep 14

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 traveler

￥215,735 total

includes taxes & fees

Aug 27 - Aug 28

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

Gaiole in chianti

￥81,665 total

includes taxes & fees

Sep 11 - Sep 12

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

Gaiole in chianti

￥88,408 total

includes taxes & fees

Sep 13 - Sep 14

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

11. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥28,070 total

includes taxes & fees

Sep 10 - Sep 11

12. Mariani Bed & Breakfast

Castellina in Chianti

Chie

￥17,726 total

includes taxes & fees

Aug 18 - Aug 19

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

13. Residenzia del Sogno

Castellina in Chianti

Katherine

￥22,088 total

includes taxes & fees

Aug 28 - Aug 29

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

14. Borgo di Erboli

Cavriglia

￥22,306 total

includes taxes & fees

Aug 27 - Aug 28

15. Villa Curina Resort

Castelnuovo Berardenga

Mary

￥32,258 total

includes taxes & fees

Aug 23 - Aug 24

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

￥29,632 total

includes taxes & fees

Aug 18 - Aug 19

17. Riserva di Fizzano Residence

Castellina in Chianti

Janet

￥35,557 total

includes taxes & fees

Sep 8 - Sep 9

Studio, Patio, Ground Floor | Terrace/patio

18. Fullino Nero

Siena

Christian

￥18,313 total

includes taxes & fees

Aug 23 - Aug 24

Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

19. Podere Vesta

Asciano

Katerine

￥31,744 total

includes taxes & fees

Aug 30 - Aug 31

20. Chianti Village Morrocco

Barberino Tavarnelle

Chris

￥17,213 total

includes taxes & fees

Sep 15 - Sep 16

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Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

10/10 Excellent

"We recently spent a week at Villa Olmi and had the most incredible time. The hotel itself is beautiful, a peaceful oasis to escape the busy city. The grounds were kept beautifully and the pool area in particular felt so pristine, plenty of fresh towels, super clean and drinks/food delivered to your sun bed- a total dream! Rooms were great with air con that kept them cool during the recent heatwave. Our room near the pool was the perfect location too, literally steps to our sun beds. The bathrooms could do with updating I feel, but they were fine and kept clean. All staff at the hotel were so lovely, warm and welcoming. The reception team were always helpful with questions we had (for example needing a different adapter for our plugs!). The wait staff were also all very attentive and friendly. The housekeeping team also- working that job during hot weather must be tough but they were so smiley and kind. Food at breakfast was great, such a good selection. The restaurant was also super tasty and a lovely setting to have dinner. One comment would be more of a varied menu, we were there for a week and the menu didn’t change so we did go elsewhere for variety. The shuttle bus was very useful and a great addition to have as it’s too far to walk into Florence. However I think a later shuttle bus to allow staying out for dinner would have been great, also dropping closer to the city centre as the 20 min walk from the bus was hard in the heat. Overall an excellent stay!"

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"

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

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Ultimo Mulino Wellness Country Hotel

10/10 Excellent

"Loved this boutique property. Stayed five nights in the newer section, Le Noci, and would love to go back. The staff were all excellent, friendly and helpful. The pool was stunning. The room was large, comfy, and quiet. Breakfast was delicious and eating on the outside terrace was wonderful as the view was incredible. The only downside was the restaurant over at the older section. Would not recommend as the waitress was rude/pushy (made the evening uncomfortable) and the food was just okay. Would recommend going to nearby Radda or Gaiole instead. Highly recommend Il Papavero in Barbischio, a few minutes east of Gaiole. The dinner we had there was the best and a highlight of the trip."

Find out more about Gaiole in Chianti

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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: Visitors like this Gaiole in Chianti vacation home rental. It 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 an espresso maker. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 24 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.

Gaiole in Chianti Vacation Rentals

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

4. Farmhouse in Chianti

5. Chianti Summer Vacation Home with Pool, Garden, and 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. Borgo di Erboli

15. Villa Curina Resort

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

17. Riserva di Fizzano Residence

18. Fullino Nero

19. Podere Vesta

20. Chianti Village Morrocco

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

Find out more about Gaiole in Chianti

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