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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 1313 Vacation Homes in Gaiole in Chianti with updated reviews, rates, and availability.

Beautiful stone house with garden and private pool.
Property grounds

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.
Farmhouse in the heart of the real chiantishire
Entrance

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (131)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
House / Villa - Monte San Savino
Property grounds

House / Villa - Monte San Savino

9.8 out of 10, Exceptional, (16)
"Es erwartet dich ein hübsches Häuschen mitten in der Natur. Etwas abgelegen, wir mochten es genau so. Natur und Ruhe pur. Die Inneneinrichtung ist schon etwas in die Jahre gekommen, aber es ist alles da was man braucht. "
House / Villa - Monte San Savino
Chianti Craft House Badia a Passignano
Point of interest

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"The apartment is at the heart of the small village, central to several great restaurants and practically across the street from the incredible 11th century abbey. The place was very clean and has been recently renovated, but still had a very historic feel to it. Emanuel, our host, was very friendly and gracious. He offered several personal recommendations to restaurants and a wine tasting at a nearby castle, all of which were great! Would definitely stay here again!"
The price is AED 636
AED 879 total
includes taxes & fees
18 Feb - 19 Feb
Chianti Craft House Badia a Passignano
Charming apartment in the Historic Center of Siena
Total view

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"This is a wonderful place. It was clean and spacious. It was well stocked. It even had bread and jam for us. It had a kitchen well-stocked with pots, pans, silverware and plates. The owner, Daniella, runs the clothing store in the same building and was very accessible and helpful. It is close by restaurants and shops and was even a nice sized Pam Local supermarket just a few doors away."
The price is AED 462
AED 798 total
includes taxes & fees
17 Feb - 18 Feb
Charming apartment in the Historic Center of Siena
The Photographer's House
Living area

The Photographer's House

9.8 out of 10, Exceptional, (9)
"The house is spacious, interesting and has everything needed for a holiday. The garden is a huge bonus - room to relax with a view (and grapes on the vine!). It was a joy to stay in an historic house in such an interesting town, with shops and restaurants within easy walking distance. We had a delicious meal at the owner’s restaurant too."
The Photographer's House
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Interior

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Wonderful Tuscan farmhouse with large spaces and panoramic views
Room

Wonderful Tuscan farmhouse with large spaces and panoramic views

10.0 out of 10, Exceptional, (11)
"We had a great time. The vila was everything we expected and our host was very accessible. I would highly recommend."
Wonderful Tuscan farmhouse with large spaces and panoramic views
Typical Tuscan Country House
Facade

Typical Tuscan Country House

10.0 out of 10, Exceptional, (114)
"Nice tidy property with everything we needed for a great stay, great location and lovely and helpful host."
Typical Tuscan Country House
House with swimming pool. Medieval village in the heart of Chianti Classico
Pool

House with swimming pool. Medieval village in the heart of Chianti Classico

10.0 out of 10, Exceptional, (106)
"Nice townhouse in a wonderfully centralized area. We wanted to explore the Chianti region from a 'home-base' and the Castellina in Chianti area was ideal for us."
House with swimming pool. Medieval village in the heart of Chianti Classico
House on Florence Hills - 4 Miles Away from Downtown Florence!
The 'Calcio Storico' bedroom with its canapy double bed

House on Florence Hills - 4 Miles Away from Downtown Florence!

9.8 out of 10, Exceptional, (41)
"The place was rustic and relaxing. Far away from thr city center so you will need transportation. The driving service was very expensive but worth it for the trip."
House on Florence Hills - 4 Miles Away from Downtown Florence!
Borgo Argiano
Exterior

Borgo Argiano

10.0 out of 10, Exceptional, (62)
"Very comfortable stay. "
Borgo Argiano
Rural family house in the Casentino with exclusive pool & gardens. Pet friendly
Relax under the Tuscan skies in our 8x5m pool

Rural family house in the Casentino with exclusive pool & gardens. Pet friendly

9.8 out of 10, Exceptional, (28)
"Maison adorable , piscine superbe . Propriétaire présent et discret . Maison confortable très calme , simple et fonctionnelle Très bon séjour"
Rural family house in the Casentino with exclusive pool & gardens. Pet friendly
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi
Pool

Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi

The price is AED 1,480
AED 1,958 total
includes taxes & fees
14 Mar - 15 Mar
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
Interior

Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

8.8 out of 10, Excellent, (10)
"The house has lots of space. We liked the area around and specially Home Restaurant near by the house "
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>
Room

A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>

10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed this beautiful cottage, which has been lovingly built and maintained by Carlo. It is close enough to Florence for easy day trips - a car is recommended for convenient access to the property, but there is ample free parking in a nearby town to head downtown by bus. Accommodations were very comfortable, we made good use of the fridge and convection cooktop, and the views are unmatched. Carlo was kind and quick to respond with any questions we had. Pro tip for those not...
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>
Capanna di Elfo by Best of Mas

Capanna di Elfo by Best of Mas

10.0 out of 10, Exceptional, (42)
"We spent an unforgettable week. Beautiful nature, wonderful Siena, Florence, San Gimignano, villa Capannna di Elfo. Exceptional hosts Angelica and Claudio!"
Capanna di Elfo by Best of Mas
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Children's area

country house with garden ,pool,children's play area ,Tuscany,15 from Florence

9.8 out of 10, Exceptional, (79)
"The place was everything we wanted and more. The perfect size house, beautiful grounds and pool, and I can’t imagine a better town (San Casciano) to be based out of. Sonia was the most wonderful host, giving us amazing information about the town and things to do in the area that we would have not found otherwise. We can’t recommend this place more highly!!!!"
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Limonaia con Piscina Privata Vista San Gimignano, Palestra e Campo da Tennis
Pool

Limonaia con Piscina Privata Vista San Gimignano, Palestra e Campo da Tennis

Limonaia con Piscina Privata Vista San Gimignano, Palestra e Campo da Tennis
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Interior

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

10.0 out of 10, Exceptional, (40)
"Stayed here the last 4 nights of our 2 week vacation. Loved the peace and quiet. No car, train or plane noise at night. Beautiful location centrally located to Voltare, Siena and other villages. The villa had all the amenities we needed. Nothing fancy but clean and efficient. Comfortable beds!! Host met us there and was very helpfull. I would recomend to others and would stay again."
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
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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Other property types in Gaiole in Chianti

Chianti Holiday House, private jacuzzi up to 6 pax
Jacuzzi in the garden

Chianti Holiday House, private jacuzzi up to 6 pax

9.4 out of 10, Exceptional, (19)
"• Pros: Beautiful grounds, garden and hot tub; dishwasher was greatly appreciated, lovely views, excellent Instructions to reach the village. Cons: • Internet/cell connectivity in village is poor and upon arrival, couldn’t connect with cell phone OR my portable wifi. I couldn’t reach the owners, and had no photos to identify the house was ours, and instructions were incomplete. Had to knock on doors which was awkward. • Password for the wifi is wrong. Passwords are case-sensitive! This wasted a...
Chianti Holiday House, private jacuzzi up to 6 pax
Hu Firenze Camping In Town
Restaurant

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1320)
"We stayed in a 2 bedroom, 2 bath unit with a small kitchenette. There was a laundramat on site which was great. It us conveniently located if you have a car. The kitchenette had a small refrigerator, a mucrowave, and a cooktop. No oven. "
Hu Firenze Camping In Town
Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (150)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is AED 527
AED 595 total
includes taxes & fees
17 Feb - 18 Feb
Il Battistero Siena - Residenza d'Epoca
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.