Gaiole in Chianti Holiday Rentals

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Our top choices for Gaiole in Chianti holiday rentals

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
The price is NZ$318
includes taxes & fees
30 Mar - 31 Mar
L' Eroico

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is NZ$351
includes taxes & fees
31 Mar - 1 Apr
Borgo Argenina

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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is NZ$1,096
includes taxes & fees
31 Mar - 1 Apr
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

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

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is NZ$1,778
includes taxes & fees
28 Mar - 29 Mar
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is NZ$12,812
includes taxes & fees
28 Mar - 29 Mar
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

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

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is NZ$618
includes taxes & fees
29 Mar - 30 Mar
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

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

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Gaiole in chianti
The price is NZ$777
includes taxes & fees
15 Apr - 16 Apr
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

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

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is NZ$887
includes taxes & fees
30 Mar - 31 Mar
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$304
includes taxes & fees
29 Mar - 30 Mar
Villa Cassia di Baccano

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is NZ$183
includes taxes & fees
29 Mar - 30 Mar
Il Pozzo di Sant'Andrea

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.0 out of 10, Very good, (60 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is NZ$85
includes taxes & fees
27 Apr - 28 Apr
hu Firenze Certosa camping in town

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Stanza pulita e fornita di tutto anche di ciabattine, spazzolino e kit cortesia. Anche la cucina. Posizione strategica, colazione completa. Personale gentile. Prezzo molto buono."
Italy
Gianmarco
The price is NZ$167
includes taxes & fees
31 Mar - 1 Apr
Tuscasì Aparthotel

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.0 out of 10, Wonderful, (9 reviews)
"Love this town. Location is great "
United States
William
The price is NZ$155
includes taxes & fees
8 Apr - 9 Apr
La Casa di Ines

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is NZ$405
includes taxes & fees
27 Apr - 28 Apr
Luxury resort in the Tuscan countryside

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is NZ$440
includes taxes & fees
13 Apr - 14 Apr
Tenuta Cantona

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is NZ$330
includes taxes & fees
4 Apr - 5 Apr
Villa Montecastello

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (170 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is NZ$176
includes taxes & fees
12 Apr - 13 Apr
Bosco della Spina

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Abbiamo trascorso una notte il 25 dicembre 2025 in questo agriturismo immerso nella campagna. Un vero angolo di pace, perfetto per staccare dalla routine e rilassarsi completamente. La struttura è curata nei minimi dettagli, pulitissima e accogliente, con un’atmosfera calda e familiare. I proprietari sono persone splendide, sempre disponibili e gentili, capaci di farti sentire come a casa fin dal primo momento. La cucina è semplicemente eccezionale: colazionei preparata con prodotti freschi e...
Italy
Roberta
The price is NZ$190
includes taxes & fees
29 Mar - 30 Mar
Casa di Campagna in Toscana

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is NZ$339
includes taxes & fees
31 Mar - 1 Apr
Antico Borgo Poggiarello

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is NZ$225
includes taxes & fees
28 Mar - 29 Mar
B&B La Fonte del Machiavelli
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gaiole in Chianti Hotel Reviews

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gaiole in Chianti holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaiole in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaiole in Chianti holiday rentals we have selected for you start as low as NZ$85 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Gaiole in Chianti?

Yes, there are holiday rentals close to the most popular sights in Gaiole in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You can relax into your holiday with a garden and a library. Another good choice for your trip to Gaiole in Chianti is Chianti Holiday House, private jacuzzi up to 6 pax.

How many holiday rentals are there in Gaiole in Chianti?

With 29 Expedia holiday rentals, you're guaranteed 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 holiday rental in Gaiole in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaiole in Chianti. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.