The Olive Cottage
14 guests
-
7 bedrooms, 9 beds
6 bathrooms
sq/ft
Ask the host anything
Do you have a question about this home or the local area?
The rustic hideaway occupies a privileged spot overlooking the Chianti hills. It caught our eye with its expansive garden, private pool and traditional charm. Some of the decor and furnishings are a little dated, but you’ll find an abundance of space along with a range of extra services available – including wine tastings and private chefs. It’s also a great option for families, with child-friendly rooms, a grass football pitch and a volleyball court. From here, it’s just 5 kilometres to the nearest amenities in Gaiole, while Siena is close enough for inspiring day trips.
The Plum Promise
- No time for average – We reject thousands of homes worldwide, so you don't have to.
- Hosts we know – With track records of high-quality hosting.
- Rated ‘Excellent’ on Trustpilot – Exceptional service before, during and after your stay.
Ask the host anything
Do you have a question about this home or the local area?
What to expect
Highlights

Take the scenic drive to Siena for a day of sightseeing

Enjoy beautiful views across Chianti while relaxing by the pool

Savour magical evenings gathered on the terrace as the sun sets
Like what you see? Explore more of this home
Home truths
Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for up to six cars.
This home is spread across two floors with two ground floor bedrooms and bathrooms.
The traditional decor here might not be to everyone's taste. It feels a little dated in parts.
Your host can provide a cot and high chair for free upon request.
Please note the swimming pool is only available for use from the 1st of May to the 30th of September.
You won't find a welcome hamper or basic essentials here, so we'd recommend packing some bits and bobs to get you started. The nearest supermarket is just 5 kilometres away.
About this stay
Amenities
Wi-fi
Parking available
Washing machine
Private pool
Garden
Balcony / patio
Patio / terrace
TV
Bedrooms & bathrooms
7 bedrooms, 9 beds
6 bathrooms
Extras
VIP services
Airport pick up
Arrange a chef
Daily cleaning
Tickets and experience booking
Additional fees
Your host can arrange a variety of services for an additional fee, including in-villa chefs, cooking lessons, wine tastings, private drivers, transfers, guided tours, children's experiences, guided walks and cycles, and event planning.
There may be some extra fees to pay here, such as charges for utilities, final cleaning fees, city tax and security deposits – all of which you may need to pay in cash to the homeowner. Please reach out during the booking process to confirm.
Extras are subject to availability and may carry additional charges. to enquire.
Local guide
About Tuscany
Perhaps the first region to come to mind when you think of holidays in Italy, there’s no denying Tuscany’s beauty. The term “Rolling hills” could have been coined here, where grapes ripen on vines in the folds of the valleys and ancient towns crown hilltops. Florence, with its fairytale ancient buildings, dramatic Ponte Vecchio over the river Arno, and Rennaisance collections in the Uffizi Gallery, has always been a big...
Explore the area
Local restaurants, cafes, museums, sites and activities, recommended by our community of hosts and travel experts

Explore Albola Castle and its vineyards
Immerse yourself in the breathtaking beauty of Albola Castle and its vineyards in the heart of Chianti. Take a guided tour of the castle, vineyards, and gardens, followed by a delightful wine-tasting and lunch experience. A must-visit for wine enthusiasts and nature lovers alike.

Explore the Paleontological Museum
Step into the small but popular Paleontological Museum and embark on a journey through millions of years. Marvel at the magnificent mammoth finds and be captivated by the well-preserved remains.

Sample the dishes at Osteria Al Ponte
Impeccable service, fine food, and a culinary experience. Indulge in their local dry-aged steak, beef tartare, and beef carpaccio. Don't miss the phenomenal bistecca fiorentina and amazing local wine too.
Get around
Airport
Amerigo Vespucci
1 hr 14 min
Pisa International
1 hr 51 min
Train station
Montevarchi-Terranuova
27 min
Local shops & services
Convenience store
12 min
Cafe
12 min
Pharmacy
12 min
Booking policies
House Rules
Children welcome (1-12 years)
Infants welcome (under 12 months)
No pets
No parties or events
No smoking
Good to know
Arrival from 16:00
Departure before 10:00
Wifi
No air con
Cancellation policy
Up until
60
days
Cancel at least 60 days before your check-in date for a 50% refund.
Not eligible for a refund once your check-in date is under 60 days away.
Host
This home is managed by Emily
This home is managed by a business on behalf of its owner. A member of their staff will be your point of contact before and during your stay. Emily and her team strive to give their guests the perfect Tuscan holiday. From their portfolio of incredible homes and villas to the tailor-made experiences they've curated, this professional team is all about Italian hospitality.
This home is nominated for the Plum Guide Award.
- Great hosts, not just great homes – We reject homes managed by hosts who don’t meet our standards of excellence.
The Plum Promise
- Every home scrutinised by experts, they have to meet our standards.
- Hosts we knowHigh-quality hosting, with track records of high-quality hosting.
- Impeccably clean, well maintained homes.
- Peace of mind in the rare event your host cancels.
- Rated ‘Excellent’ on Trustpilot, delivering exceptional service before, during and after your stay.