Gaiole in Chianti Apartment Rentals from CA $144

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

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Our top choices for Gaiole in Chianti apartments

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

Gaiole in Chianti

Mariah M.

CA $423 total

includes taxes & fees

Aug 31 - Sep 1

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

Gaiole in chianti

CA $555 total

includes taxes & fees

Sep 13 - Sep 14

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

Gaiole in chianti

CA $711 total

includes taxes & fees

Sep 11 - Sep 12

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

Gaiole in chianti

CA $770 total

includes taxes & fees

Sep 13 - Sep 14

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

5. Borgo di Erboli

Cavriglia

CA $196 total

includes taxes & fees

Aug 27 - Aug 28

6. Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

Toscana

Wendy T.

CA $450 total

includes taxes & fees

Aug 20 - Aug 21

7. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

CA $210 total

includes taxes & fees

Aug 25 - Aug 26

8. A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi

Cavriglia

CA $165 total

includes taxes & fees

Aug 18 - Aug 19

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Top Gaiole in Chianti Hotel Reviews

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."

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."

Find out more about Gaiole in Chianti

Gaiole in Chianti Apartments information

Number of reviews	165
Accommodation	2716 Apartments
Lowest Price	CA $144
Highest Price	CA $770

Frequently asked questions

What's it like to stay at an apartment in Gaiole in Chianti?

You can search through 54 apartments in Gaiole in Chianti for your trip. In this quaint area, you can visit the spas and enjoy the wineries.

How do you know if an apartment is a good option for you?

Often more spacious than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in a quieter area.

What's the top apartment I should consider for a stay in Gaiole in Chianti?

Below are some of the more popular apartments in the area to choose from: Villa Il Palagio: Located in Rignano sull'Arno, 15.9 mi/25.6 km from the heart of Gaiole in Chianti. Includes free WiFi and premium mattresses. A restaurant and free parking are on site. ApartHotel Anghel: Located 12.4 mi/20 km away in Siena. Free WiFi and separate dining areas are included. Free parking and onsite laundry facilities are on site. Casa Ciseri: Located in Siena, 11.5 mi/18.6 km away. Includes free WiFi and Smart TVs. Valet parking and onsite laundry facilities are on site. Regis Condo: Located 11.7 mi/18.9 km away in Siena. Free WiFi, separate dining areas, and premium mattresses are included. Access to valet parking is available on site. Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany): It's located in Arezzo, 22.4 mi/36 km from Gaiole in Chianti. Includes free WiFi, private patios, and fireplaces.

How many apartments are there in Gaiole in Chianti?

Expedia has 54 apartments to book in Gaiole in Chianti.

What can I expect from the weather during my trip to Gaiole in Chianti?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Gaiole in Chianti. The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Gaiole in Chianti is 37 inches.

What should I see in Gaiole in Chianti?

Gaiole in Chianti is known for its wineries and spas. 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. Other places in town to visit include Meleto Castle and Badia a Coltibuono.

What's the best way to get to and around Gaiole in Chianti?

Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Florence Airport, Peretola (FLR), which is located 25.9 mi (41.7 km) from the heart of the city. If you'd like to explore around the area, you may want a rental car for your journey.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti apartments

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

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

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

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

5. Borgo di Erboli

6. Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

7. Casa Vacanze Squarcialupi

8. A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi

9. Cennano Suite - enter apartment

10. Apartment 'Casale Rosennano - Loggia' with Shared Garden & Wi-Fi

11. Villa Norcenni Aparthotel

12. ‘Nido Blu Loft’ Apartment with Shared Pool, Private Garden, and Wi-Fi

13. Apartment at Heart of Panzano

14. ApartHotel Anghel

15. Tuscany Family Getaway Near Florence | Parking + AC | Sleeps 8

16. Regis Condo

17. ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve

18. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

19. LE BOTTI FIORENTINE

20. Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Radisson Blu Hotel, Florence

Find out more about Gaiole in Chianti

Gaiole in Chianti Apartments information

Frequently asked questions

Explore a world of travel with Expedia