We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Gaiole in Chianti Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
103 rentals in Gaiole in Chianti.
Sort by:
Tripadvisor Sort
LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS, holiday rental in Gaiole in Chianti

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews., holiday rental in Gaiole in Chianti

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

5 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casacorvo Minore *20% late Summer Discounts *Exclusive EV Point Included*, holiday rental in Gaiole in Chianti

Casacorvo Minore *20% late Summer Discounts *Exclusive EV Point Included*

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Secluded private retreat, but strategic to main attractions of Chianti hills, holiday rental in Gaiole in Chianti

Secluded private retreat, but strategic to main attractions of Chianti hills

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Enjoy Breathtaking Views at Boutique Farmhouse & Infinity Pool, holiday rental in Gaiole in Chianti

Enjoy Breathtaking Views at Boutique Farmhouse & Infinity Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Casacorvo Maggiore: *20% Late Summer Discounts* Exclusive EV Point Included*, holiday rental in Gaiole in Chianti

Casacorvo Maggiore: *20% Late Summer Discounts* Exclusive EV Point Included*

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Private secluded retreat in the Chianti hills between Siena and Florence, holiday rental in Gaiole in Chianti

Private secluded retreat in the Chianti hills between Siena and Florence

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool, holiday rental in Gaiole in Chianti

Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6, holiday rental in Gaiole in Chianti

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
LA VACANZA NEL CUORE DEL CHIANTI, holiday rental in Gaiole in Chianti

A HOLIDAY IN THE HEART OF CHIANTI

2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Gaiole in Chianti rentals sent straight to your email!
Fienile con vista sui vigneti, holiday rental in Gaiole in Chianti

Barn overlooking the vineyards

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PODERE MONTELUCCI - GAIOLE IN CHIANTI, holiday rental in Gaiole in Chianti

PODERE MONTELUCCI - GAIOLE IN CHIANTI

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lodge Ricavo con piscina riscaldata e jacuzzi esterna, holiday rental in Gaiole in Chianti

Lodge Ricavo con piscina riscaldata e jacuzzi esterna

12 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Casa Ciaccheri, holiday rental in Gaiole in Chianti

Casa Ciaccheri

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Eracle, holiday rental in Gaiole in Chianti

Villa Eracle

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
San Sano hamlet in the Heart of the Chianti, the Best choice in Tuscany !, holiday rental in Gaiole in Chianti

San Sano hamlet in the Heart of the Chianti, the Best choice in Tuscany !

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Gaiole, Borgo di Gaiole, holiday rental in Gaiole in Chianti

Villa Gaiole, Borgo di Gaiole

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hilltop Poolside 2 Bedroom Villa in Chianti, holiday rental in Gaiole in Chianti

Hilltop Poolside 2 Bedroom Villa in Chianti

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
UNA VACANZA DA SOGNO, holiday rental in Gaiole in Chianti

UNA VACANZA DA SOGNO

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Torre di Cancelli - luxury villa in Chianti!, holiday rental in Gaiole in Chianti

Torre di Cancelli - luxury villa in Chianti!

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 Zimmer Unterkunft in Gaiole in Chianti SI, holiday rental in Gaiole in Chianti

2 Zimmer Unterkunft in Gaiole in Chianti SI

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Nido in Chianti Shire, holiday rental in Gaiole in Chianti

Charming Nido in Chianti Shire

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST, holiday rental in Gaiole in Chianti

TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Exclusive and reserved in Chianti - Quercia, holiday rental in Gaiole in Chianti

Exclusive and reserved in Chianti - Quercia

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Giardino, Borgo Gaiole, holiday rental in Gaiole in Chianti

Casa Giardino, Borgo Gaiole

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Ginevra casa storica, holiday rental in Gaiole in Chianti

Geneva House historic home

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti, holiday rental in Gaiole in Chianti

Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Il Borghetto, Gaiole-in-Chianti, holiday rental in Gaiole in Chianti

Il Borghetto, Gaiole-in-Chianti

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
La Pieve Marsina, Chianti, Apartment  La Pieve, holiday rental in Gaiole in Chianti

La Pieve Marsina, Chianti, Apartment La Pieve

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa il Mandorlo private garden - pool, holiday rental in Gaiole in Chianti

Casa il Mandorlo private garden - pool

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
La Canonica di Vertine, holiday rental in Gaiole in Chianti

La Canonica di Vertine

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Vertine Spa Apartment, holiday rental in Gaiole in Chianti

Vertine Spa Apartment

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casina Di Mello, holiday rental in Gaiole in Chianti

Casina Di Mello

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Refolo A, holiday rental in Gaiole in Chianti

Casa Refolo A

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
La Pieve Marsina, Tuscany, Chianti, Il Pozzo, holiday rental in Gaiole in Chianti

La Pieve Marsina, Tuscany, Chianti, Il Pozzo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Abbazia del 1051, holiday rental in Gaiole in Chianti

Abbey of 1051

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
XI CENTURY ANTIQUE FARMHOUSE WITH CHIANTI LANDSCAPE IN GAIOLE, holiday rental in Gaiole in Chianti

XI CENTURY ANTIQUE FARMHOUSE WITH CHIANTI LANDSCAPE IN GAIOLE

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Podere Lucignano Secondo - Charming Tuscan Villa, holiday rental in Gaiole in Chianti

Podere Lucignano Secondo - Charming Tuscan Villa

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Gaiole Apartment - Gaiole Apartment 40, holiday rental in Gaiole in Chianti

Gaiole Apartment - Gaiole Apartment 40

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
VIGNE DEL CHIANTI RESORT, holiday rental in Gaiole in Chianti

VIGNE DEL CHIANTI RESORT

15 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Casa vacanze a Bucine ID 3467, holiday rental in Gaiole in Chianti

Casa vacanze a Bucine ID 3467

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Casanuova, holiday rental in Gaiole in Chianti

Villa Casanuova

11 bedrooms
11 bathrooms
Sleeps 22
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
CASA DEL CIRICA, holiday rental in Gaiole in Chianti

CASA DEL CIRICA

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Amazing stay in the heart of Tuscany, Chianti area, holiday rental in Gaiole in Chianti

Amazing stay in the heart of Tuscany, Chianti area

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Country House a Gaiole in Chianti ID 3471, holiday rental in Gaiole in Chianti

Country House a Gaiole in Chianti ID 3471

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa del Cirica, holiday rental in Gaiole in Chianti

Casa del Cirica

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Castello Di Meleto, holiday rental in Gaiole in Chianti

Castello Di Meleto

7 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Caciaia, holiday rental in Gaiole in Chianti

Caciaia

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Canonica, holiday rental in Gaiole in Chianti

Canonica

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Fauno D, holiday rental in Gaiole in Chianti

Villa Fauno D

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Previous
Frequently Asked Questions about Gaiole in Chianti