Cypress Sky
18 guests
-
9 bedrooms, 12 beds
9 bathrooms
Ask the host anything
Do you have a question about this home or the local area?
Those seeking a rustic getaway in Italy will adore this home. It comprises a converted farmhouse and barn in a beautiful spot in the Chianti Hills, surrounded by vineyards and olive groves. It’s between Florence and Siena, so you’ll have plenty of choice when it comes to planning day trips. The villa boasts an infinity pool overlooking the valley, and a panoramic terrace where you can dine alfresco. The kitchen will delight home cooks, but your host can arrange a private chef if you want to leave it to the professionals.
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
Explore the Chianti countryside's vineyards and hiking trails
Dine alfresco on the terrace – why not book a personal chef?
Admire sweeping valley views from the infinity pool and garden
Like what you see? Explore more of this home
Home truths
This home comprises the main villa – converted from a farmhouse – and a converted barn, so you won’t all be sleeping under the same roof.
There are stairs to climb at this home so it may not be suitable for those with reduced mobility.
While not every bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home.
About this stay
Amenities
Outdoor seating
Wi-fi
Air conditioning
Private outdoor pool
Garden
Patio / terrace
TV
Child friendly
Bedrooms & bathrooms
9 bedrooms, 12 beds
9 bathrooms
Extras
VIP services
Airport pick up
Arrange a chef
Baby sitting
Daily cleaning
Fridge fills
Massage
Tickets and experience booking
Additional fees
Your host can help arrange personal chefs, cooking classes, pre-arrival grocery shopping, physiotherapists and massages, yoga sessions, private drivers, babysitters, extra cleanings, truffle hunting experiences, wine tours and tastings, and more for an additional fee.
Speak to your host if you’d like to arrange an event or an event planner – an additional fee may apply.
Additional fees subject to a 3.5% handling charge.
Extras are subject to availability. Please enquire with your host.
Local guide
About Chianti
Chianti is a region situated in the heart of Tuscany, known for its picturesque rolling hills and sun-drenched landscape. Discover and enjoy locally produced wines while exploring the charming vineyards and family-owned wineries. You’ll find plenty of scenic towns and villages – from Montefioralle to Castellina, which are not to be missed. Here you can wander the narrow Medieval streets, and explore historic churches and impressive castles. Immerse yourself in the...
Explore the area
Local restaurants, cafes, museums, sites and activities, recommended by our community of hosts and travel experts
Explore Antica Macelleria Falorni
Indulge in a delightful culinary experience at this local gem. Sample the finest Tuscan meats, cheeses, and wines while learning about the art of curing. Don't miss the mouthwatering porchetta sandwich.
Try the oat-grilled meats at Enoteca Ristorante il Gallo Nero
Experience the outstanding food and great service at this Tuscan restaurant. Indulge in oak-grilled meats, handmade pasta, and Chianti wines while enjoying a gorgeous sunset view.
Enjoy the atmosphere at Ristorante Pizzeria La Cantina
Enjoy fabulous food and excellent service at this tavern-like restaurant. Indulge in delicious pizza, antipasti platters, and grilled meats in a charming setting with exposed brick and stone.
Explore the charm of Piazza Matteotti
Immerse yourself in the heart of Chianti at this bustling square, lined with shops and offering a picturesque setting in an old town.
Explore the historic Castello di Verrazzano
Imposing hillside castle and winery offering extensive tours, Chianti tastings, and delightful al fresco dining. Indulge in delicious wines, balsamic vinegar, and a delectable lunch while admiring stunning views of Greve in Chianti.
Explore the historic charm of Montefioralle
Step back in time as you wander through the quaint streets of Montefioralle, a hidden gem perched atop a Tuscan hill. Discover its ancient castle, visit the Jewish Square with its historic shops, and enjoy panoramic views of Val d'Orcia.
Get around
Airport
Amerigo Vespucci
1 hr 15 min
Pisa International
1 hr 50 min
Bologna Guglielmo Marconi
2 hr 7 min
Train station
Figline Valdarno
56 min
Bus stop
Vigne Di Vitigliano_V
10 min
Local shops & services
Convenience store
16 min
Cafe
17 min
Pharmacy
18 min
Points of interest
Beach
Stazione Balneare Merse
1 hr 29 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
Air con
Wifi
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 Nathan
This home is managed directly by a business. A member of their staff will be your point of contact before and during your stay. Nathan and his team pride themselves on transparency, professionalism, and helpfulness. They're always on hand when you need them, ensuring you have the holiday you deserve with memories that will last a lifetime.
Registration or licence number: IT048021B5Z76KLPWG.
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.
