Gaiole in Chianti Vacation Rentals from ￥9,009: 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

￥27,837 total

includes taxes & fees

Aug 24 - Aug 25

2. Borgo Argenina

Gaiole in Chianti

Sabatino

￥47,241 total

includes taxes & fees

Aug 23 - Aug 24

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

Gaiole in Chianti

￥348,111 total

includes taxes & fees

Aug 31 - Sep 1

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

Gaiole in Chianti

Mariah M.

￥50,387 total

includes taxes & fees

Sep 1 - Sep 2

5. 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.

￥102,795 total

includes taxes & fees

Sep 1 - Sep 2

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

Gaiole in Chianti

Bernard K.

￥252,452 total

includes taxes & fees

Aug 25 - Aug 26

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

Gaiole in chianti

￥88,196 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

￥215,217 total

includes taxes & fees

Aug 27 - Aug 28

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

Gaiole in chianti

￥63,529 total

includes taxes & fees

Sep 13 - Sep 14

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

10. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥28,002 total

includes taxes & fees

Sep 10 - Sep 11

11. Mariani Bed & Breakfast

Castellina in Chianti

Chie

￥17,670 total

includes taxes & fees

Aug 20 - Aug 21

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

12. Borgo di Erboli

Cavriglia

￥22,191 total

includes taxes & fees

Aug 18 - Aug 19

13. Villa Curina Resort

Castelnuovo Berardenga

Mary

￥30,610 total

includes taxes & fees

Sep 13 - Sep 14

14. 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

￥29,560 total

includes taxes & fees

Aug 17 - Aug 18

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

15. Residenzia del Sogno

Castellina in Chianti

Katherine

￥22,036 total

includes taxes & fees

Aug 28 - Aug 29

Studio, Patio, Ground Floor | Terrace/patio

16. Fullino Nero

Siena

Christian

￥19,953 total

includes taxes & fees

Aug 19 - Aug 20

Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

17. La Terrazza Sul Campo Rooming House

Siena City Centre

Margaret

￥21,880 total

includes taxes & fees

Aug 26 - Aug 27

18. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

￥17,533 total

includes taxes & fees

Aug 16 - Aug 17

19. Riserva di Fizzano Residence

Castellina in Chianti

Janet

￥35,470 total

includes taxes & fees

Sep 8 - Sep 9

20. Chianti Village Morrocco

Barberino Tavarnelle

Chris

￥18,103 total

includes taxes & fees

Sep 1 - Sep 2

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Top Gaiole in Chianti Hotel Reviews

Villa Casagrande Resort & SPA

10/10 Excellent

"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"

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."

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

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

5. Farmhouse in Chianti

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

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

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

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

10. Villa di Sotto

11. Mariani Bed & Breakfast

12. Borgo di Erboli

13. Villa Curina Resort

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

15. Residenzia del Sogno

16. Fullino Nero

17. La Terrazza Sul Campo Rooming House

18. Hu Norcenni Girasole Village

19. Riserva di Fizzano Residence

20. Chianti Village Morrocco

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Villa Casagrande Resort & SPA

Find out more about Gaiole in Chianti

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