Gaiole in Chianti Vacation Rentals from $47: 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 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

$128 nightly

Nov 5 - Nov 6

Total with taxes and fees

A stone building with a garden in front.

2. Borgo Argenina

Gaiole in Chianti

Tatevik

$180 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

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

Gaiole in Chianti

Mariah M.

$394 nightly

Oct 31 - Nov 1

Total with taxes and fees

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

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

Gaiole in Chianti

$1,130 nightly

Oct 18 - Oct 19

Total with taxes and fees

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.

$2,034 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

6. 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.

$511 nightly

Oct 18 - Oct 19

Total with taxes and fees

A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

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

Gaiole in chianti

$392 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

Gaiole in chianti

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

Gaiole in chianti

$553 nightly

Oct 18 - Oct 19

Total with taxes and fees

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

10. Villa di Sotto

Castelnuovo Berardenga

Philippe

$162 nightly

Oct 20 - Oct 21

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

11. Residenzia del Sogno

Castellina in Chianti

Katherine

$119 nightly

Oct 16 - Oct 17

Total with taxes and fees

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

12. Villa Curina Resort

Castelnuovo Berardenga

Deanna

$121 nightly

Oct 20 - Oct 21

Total with taxes and fees

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

13. 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

$177 nightly

Oct 16 - Oct 17

Total with taxes and fees

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

14. Riserva di Fizzano Residence

Castellina in Chianti

Janet

$173 nightly

Oct 19 - Oct 20

Total with taxes and fees

A stone building with multiple windows and a chimney.

15. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

$128 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

16. Ca' Bianca Tuscany Relais

Siena

Talha

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

$139 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

18. Chianti Village Morrocco

Tavarnelle Val di Pesa

Winonah

$76 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

19. Terre di Baccio

Greve in Chianti

Gage

$304 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

20. Tuscasì Aparthotel

Sovicille

Sergey

$66 nightly

Nov 4 - Nov 5

Total with taxes and fees

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Top Gaiole in Chianti Hotel Reviews

La Certosa di Pontignano

10/10 Excellent

"Absolutely amazing stay! The room was clean, large with a great view. The staff was always willing to help. Could not have asked for more. Highly recommend!"

Hu Firenze Camping In Town

10/10 Excellent

"It was a really nice experience staying at Hu Firenze. It was away from the hustle and bustle of the city and the main tourist areas, while a bus stop right across the street made it easy to get to the city centre. We also got to enjoy a bit of the Tuscan countryside experience. The only issue was that there is another Hu campsite called Hu Certosa, so you need to be careful not to book the wrong one, especially when travelling in a group and everyone is booking separately. This happened to us, but fortunately, the staff allowed my brother to stay with us since our accommodation had an extra bed. However, we had already paid for a tent at Hu Certosa. My recommendation would be to start breakfast earlier than 7:30 a.m. This would allow guests to leave at different times and help avoid long queues at the bus stop."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"From the moment we arrived to the moment we left the staff were fantastic. Lapo, at the front desk, was extremely helpful in making last minute arrangements for anything we needed. The entire staff from the porters, bar tenders, cleaning staff and managers were friendly and accommodating. The property was picturesque and absolutely stunning. We wish we would have stayed more days just to enjoy the property itself. If you're having an afternoon drink on the patio bar or enjoying a scrumptious evening meal in the restaurant you will not be disappointed."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Gaiole in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $47 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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Things to do in Gaiole in Chianti

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 kitchenware. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 18 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.

Room 1

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

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

6. Farmhouse in Chianti

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

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

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

10. Villa di Sotto

11. Residenzia del Sogno

12. Villa Curina Resort

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

14. Riserva di Fizzano Residence

15. Agriturismo La Ferrozzola

16. Ca' Bianca Tuscany Relais

17. Relais Villa Belpoggio - Residenza d'Epoca

18. Chianti Village Morrocco

19. Terre di Baccio

20. Tuscasì Aparthotel

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

La Certosa di Pontignano

Castello di Tornano Wine Resort

Hu Firenze Camping In Town

Hotel Casolare Le Terre Rosse

Grand Hotel Continental Siena – Starhotels Collezione

Radisson Blu Hotel, Florence

Castello di Spaltenna- Small Luxury Hotels of the World

Villa I Barronci Resort & Spa

Hotel Mulino di Firenze, WorldHotels Crafted

Find out more about Gaiole in Chianti

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