Gaiole in Chianti Vacation Rentals from ￥9,196: 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.

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

￥23,797 total

includes taxes & fees

Nov 29 - Nov 30

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

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

Gaiole in Chianti

￥149,572 total

includes taxes & fees

Nov 15 - Nov 16

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

3. 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.

￥84,882 total

includes taxes & fees

Nov 25 - Nov 26

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

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

Gaiole in Chianti

Bernard K.

￥274,521 total

includes taxes & fees

Nov 17 - Nov 18

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

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

Gaiole in chianti

￥51,550 total

includes taxes & fees

Dec 13 - Dec 14

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

Gaiole in chianti

￥54,996 total

includes taxes & fees

Dec 13 - Dec 14

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

Gaiole in chianti

￥73,093 total

includes taxes & fees

Dec 13 - Dec 14

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

8. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

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

￥26,807 total

includes taxes & fees

Nov 23 - Nov 24

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

9. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

￥22,943 total

includes taxes & fees

Nov 29 - Nov 30

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

10. Terre di Baccio

Greve in Chianti

Gage

￥47,768 total

includes taxes & fees

Nov 15 - Nov 16

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

11. Relais Villa Olmo - Place of Charme

Impruneta

Michael

￥16,223 total

includes taxes & fees

Nov 29 - Nov 30

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

12. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

￥20,997 total

includes taxes & fees

Nov 17 - Nov 18

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

13. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

￥10,469 total

includes taxes & fees

Dec 14 - Dec 15

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

14. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Kristina

￥27,808 total

includes taxes & fees

Dec 7 - Dec 8

A cozy living room with a stone wall, a wine rack, and two sofas.

15. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

￥16,615 total

includes taxes & fees

Nov 27 - Nov 28

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

16. Palazzo Pacini

Colle di Val d'Elsa

John

￥20,824 total

includes taxes & fees

Dec 3 - Dec 4

A dining area with a table set for two, featuring a view of greenery through a window.

17. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

￥25,879 total

includes taxes & fees

Nov 22 - Nov 23

A bathroom with a window view of a historic building and a tiled roof.

18. Siena Vip

Siena City Centre

John

￥16,211 total

includes taxes & fees

Nov 15 - Nov 16

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.

19. Tuscasì Aparthotel

Sovicille

Sergey

￥13,664 total

includes taxes & fees

Nov 19 - Nov 20

A rustic stone building with a courtyard.

20. Fullino Nero

Siena

Annie

￥18,435 total

includes taxes & fees

Nov 17 - Nov 18

View all properties

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

L' Eroico

Gaiole in Chianti

10/10 Excellent

Angela

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

The Club House

Castelnuovo Berardenga

10/10 Excellent

debbie

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Anonymous traveler

A motorcycle parked in front of a brick building with arched doorways and a street lamp.

Torre del Fuggisole

Siena City Centre

10/10 Excellent

Charles

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

La Dimora Dei Monaci

Siena City Centre

10/10 Excellent

we stayed for 4 nights and used Seina as our base for our first visit to Tuscany. The owners were very helpful. They provided maps and information on all the local sights, plus some history of the town. One night we asked them to make dinner reservations and they had to call over 10 places due to a busy night. But they found us a great restaurant for dinner. Another day they provide a detailed schedule for buses to visit one of the towns we were interested in. The B&B is very close to the...

Alan

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

Villa del Sole Siena

Siena City Centre

10/10 Excellent

Linna

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

Palazzo di Valli

Siena

10/10 Excellent

We stayed 3 nights at Palazzo di Valli in late April 2022. The property is beautiful and located in a quiet residential area just south of the city's center. It sits on a hill overlooking a valley, and has it's own orchard and flower gardens. Instead of waking up to the sound of motorcycles and delivery trucks under your window, we woke up to chirping birds. Hosts Lorenzo and Giancarlo were wonderful, offering us recommendations, and helping arrange reservations and transportation. It's a bit of...

Joan

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

Relais degli Angeli

Siena City Centre

10/10 Excellent

Stained here at the end of an eight day trip around Italy. This hotel was head and shoulders above the others I visited, it is a boutique hotel of seven rooms. Our room was a suite. It was bigger than many apartments, with a large living room with daybed, a beautiful master bathroom with jetted tub and separate shower with jets overhead as well as side jets, ample closet storage, fridge, and safe. The rooms here have antique furniture and hand painted ceilings. I loved the breakfast on the...

Susie

A brick building with two arched windows, one with a metal grill and the other with a decorative glass design.

Hotel Palazzetto Rosso

Siena City Centre

10/10 Excellent

A Beautiful and Unique Stay in the Heart of Siena! Our stay at Hotel Palazzetto Rosso was an incredible experience! The atmosphere was absolutely amazing, with stunning medieval architecture that perfectly captures the historic charm of Siena. The hotel beautifully blends its centuries-old character with modern comforts, creating a truly unique and memorable experience. The staff was exceptionally friendly and accommodating, especially when it came to our late arrival. They went above and...

Thomas

A traditional stone building with a garden featuring geometric hedges and potted plants.

Badia a Coltibuono

Gaiole in Chianti

10/10 Excellent

Grace

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Gary

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

10/10 Excellent

Sarah

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

Borgo Grondaie

Siena

10/10 Excellent

tmcmaus

Relais Villa Olmo - Place of Charme

Impruneta

10/10 Excellent

Anonymous traveler

An outdoor dining area with tables and chairs, a striped canopy, and a view of the landscape.

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

10/10 Excellent

We are very frequent travelers who have never been to the Villa il Poggiale before and loved it. We visited in late September - not too hot and the evenings were cool. Perfect time to go. Federica, Irene, and the entire staff were absolutely wonderful from arranging our to/from airport transportation to making us feel at home. The grounds were lovely, although the pool was not heated in late September. We had breakfast everyday at the Villa - the chef does a wonderful job. They have a...

William

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

COMO Castello Del Nero

Tavarnelle Val di Pesa

10/10 Excellent

Lauren

Find out more about Gaiole in Chianti

Search for holiday rentals in Gaiole in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Gaiole in Chianti using one of the methods below:

View our selection of featured holiday rentals in Gaiole in Chianti
Use the map to find apartments and other holiday homes in the Gaiole in Chianti neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Gaiole in Chianti while they last

Look no further and take a look at our great range of rental properties 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.

Explore a world of travel with Expedia

Car rental Greve in Chianti
Standard Link for Car rental Greve in Chianti

Radda in Chianti Vacation Rentals
Standard Link for Radda in Chianti Vacation Rentals

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 rentals

1. L' Eroico

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

3. Farmhouse in Chianti

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

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

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

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

8. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

9. Agriturismo La Ferrozzola

10. Terre di Baccio

11. Relais Villa Olmo - Place of Charme

12. Casa Vacanze Squarcialupi

13. Chianti Village Morrocco

14. Relais Villa Belpoggio - Residenza d'Epoca

15. Villa Cassia di Baccano

16. Palazzo Pacini

17. La Locanda di Pietracupa

18. Siena Vip

19. Tuscasì Aparthotel

20. Fullino Nero

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

L' Eroico

10/10 Excellent

Find out more about Gaiole in Chianti

Frequently Asked Questions

Can I find vacation rentals in Gaiole in Chianti?

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

How many vacation rentals are there in Gaiole in Chianti?

What’s there to see and do in Gaiole in Chianti?

What’s a vacation rental in Gaiole in Chianti like?

Explore a world of travel with Expedia