Gaiole in Chianti Vacation Home Rentals from CA $141: Search Top Private Vacation Homes for Rent

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti vacation homes

1. 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.

CA $891 total

includes taxes & fees

Sep 1 - Sep 2

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

Gaiole in Chianti

CA $2,749 total

includes taxes & fees

Aug 31 - Sep 1

3. 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

CA $256 total

includes taxes & fees

Aug 18 - Aug 19

4. Villa with large garden in the Chianti hills

Siena

Julie H.

CA $222 total

includes taxes & fees

Sep 1 - Sep 2

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

CA $464 total

includes taxes & fees

Aug 18 - Aug 19

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

CA $262 total

includes taxes & fees

Aug 19 - Aug 20

7. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Rosennano

CA $410 total

includes taxes & fees

Aug 31 - Sep 1

8. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $433 total

includes taxes & fees

Aug 24 - Aug 25

9. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

CA $267 total

includes taxes & fees

Aug 30 - Aug 31

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

CA $594 total

includes taxes & fees

Aug 20 - Aug 21

11. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Casetta

CA $170 total

includes taxes & fees

Sep 14 - Sep 15

12. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

CA $589 total

includes taxes & fees

Sep 15 - Sep 16

13. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Bucine

CA $589 total

includes taxes & fees

Sep 15 - Sep 16

14. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

Anonymous traveller

CA $694 total

includes taxes & fees

Sep 11 - Sep 12

15. The Arch Among the Hills of Castellina

Topina

CA $525 total

includes taxes & fees

Sep 16 - Sep 17

16. Little cozy house

Loro Ciuffenna

CA $141 total

includes taxes & fees

Aug 20 - Aug 21

17. Vana Hills House - Three Bedroom House, Sleeps 8

Monteriggioni

CA $406 total

includes taxes & fees

Sep 1 - Sep 2

18. Exclusive Stone Tower.

Casciano

Ryan C.

CA $260 total

includes taxes & fees

Aug 24 - Aug 25

19. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Figline Valdarno

CA $388 total

includes taxes & fees

Aug 24 - Aug 25

20. House with views of the Chianti

impruneta

Chase B.

CA $359 total

includes taxes & fees

Aug 30 - Aug 31

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Top Gaiole in Chianti Hotel Reviews

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

Radisson Blu Hotel, Florence

10/10 Excellent

"We weren’t sure whether to book our 2 night stay based on other reviews, but we are so glad that we did. We arrived by car and there was ample free parking on site. A car park in Florence was recommended by the lobby staff that was a 15 minute drive and had lots of spaces and not insanely priced, the centre was then a 10 minute walk from there. The hotel was spotless, easy check in, big room. Pool was great, the kids loved the splash area and there was even a FREE arcade room in the basement! The kids loved it. Breakfast was a god buffet with plenty for me as vegetarian and gluten free bread etc for my wife. Plenty of fruit and pastries for the kids! The beds were large and comfortable, air con great. Room has a fridge and some free waters which was a nice touch along with a coffee machine. A really good stay, well priced and I wouldn’t hesitate to stay here again if coming to Florence. There is a shuttle bus that you can book a seat on too, but we didn’t use this as had the car. Great hotel"

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."

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews	118
Accommodation	1523 Vacation Homes
Lowest Price	CA $141
Highest Price	CA $2,749

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti vacation homes

1. Farmhouse in Chianti

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

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

4. Villa with large garden in the Chianti hills

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

7. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

8. Casa Marisa in Castellina in Chianti

9. Chianti Craft House Badia a Passignano

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

11. Peaceful corner with garden between Chianti and Crete, very close to Old Town

12. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

13. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

14. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

15. The Arch Among the Hills of Castellina

16. Little cozy house

17. Vana Hills House - Three Bedroom House, Sleeps 8

18. Exclusive Stone Tower.

19. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

20. House with views of the Chianti

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Athena

Hu Firenze Camping In Town

Radisson Blu Hotel, Florence

Villa Scacciapensieri Boutique Hotel

Villa Olmi Firenze

Castello di Tornano Wine Resort

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

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Explore a world of travel with Expedia

Gaiole in Chianti Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti vacation homes

1. Farmhouse in Chianti

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

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

4. Villa with large garden in the Chianti hills

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

7. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

8. Casa Marisa in Castellina in Chianti

9. Chianti Craft House Badia a Passignano

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

11. Peaceful corner with garden between Chianti and Crete, very close to Old Town

12. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

13. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

14. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

15. The Arch Among the Hills of Castellina

16. Little cozy house

17. Vana Hills House - Three Bedroom House, Sleeps 8

18. Exclusive Stone Tower.

19. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

20. House with views of the Chianti

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Athena

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Explore a world of travel with Expedia