Gaiole in Chianti Vacation Rentals

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Our top choices for Gaiole in Chianti vacation 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 CA $226
CA $261 total
includes taxes & fees
Mar 31 - Apr 1
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 CA $243
CA $280 total
includes taxes & fees
Mar 31 - Apr 1
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 CA $737
CA $880 total
includes taxes & fees
Mar 28 - Mar 29
'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 CA $1,381
CA $1,419 total
includes taxes & fees
Mar 28 - Mar 29
"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 CA $9,429
CA $10,228 total
includes taxes & fees
Mar 28 - Mar 29
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 CA $487
CA $494 total
includes taxes & fees
Mar 29 - Mar 30
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 CA $614
CA $620 total
includes taxes & fees
Apr 15 - Apr 16
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 CA $701
CA $707 total
includes taxes & fees
Mar 29 - Mar 30
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 CA $221
CA $243 total
includes taxes & fees
Apr 9 - Apr 10
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 CA $131
CA $151 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $59
CA $70 total
includes taxes & fees
Apr 2 - Apr 3
hu Firenze Certosa camping in town

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $102
CA $133 total
includes taxes & fees
Apr 2 - Apr 3
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 CA $112
CA $132 total
includes taxes & fees
Mar 30 - Mar 31
La Casa di Ines

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is CA $299
CA $334 total
includes taxes & fees
Apr 27 - Apr 28
Luxury resort in the Tuscan countryside

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is CA $169
CA $277 total
includes taxes & fees
Apr 1 - Apr 2
Tenuta Cantona

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is CA $235
CA $264 total
includes taxes & fees
Apr 3 - Apr 4
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 CA $116
CA $141 total
includes taxes & fees
Apr 12 - Apr 13
Bosco della Spina

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is CA $134
CA $152 total
includes taxes & fees
Mar 29 - Mar 30
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 CA $242
CA $271 total
includes taxes & fees
Apr 27 - Apr 28
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 CA $157
CA $180 total
includes taxes & fees
Mar 28 - Mar 29
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gaiole in Chianti. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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: You might want to consider this vacation home rental near Gaiole in Chianti, which 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 a coffee maker. You can relax into your vacation 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 vacation rentals are there in Gaiole in Chianti?

With 29 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.