Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views

Photo gallery for Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views

A balcony with a view of a hilly landscape, a brick wall, and a window with a curtain.
A balcony with two arched windows, each with a view of a rural landscape.
A cozy living room with a staircase, a dining area, and a staircase leading to an upper floor.
A narrow street lined with stone buildings, some with arched windows and doorways, and potted plants along the sidewalk.
A dining area with a wooden table and chairs, a kitchen in the background, a staircase, and a painting on the wall.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Rooftop terrace
    A rare find - enjoy stunning views from the rooftop terrace.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Rooftop terrace

Explore the area

View map
Barberino Val D'elsa, Toscana
  • Place, Santa Lucia al Borghetto Church
    ‪10 min drive‬
  • Place, Ponte Vecchio
    ‪48 min drive‬
  • Place, Piazza di Santa Maria Novella
    ‪51 min drive‬
  • Airport, Florence (FLR-Peretola)
    ‪50 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Bidet · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views

Our well appointed two bedroom/two bath apartment sits within the walls of an ancient fortress town midway between Florence and Siena. We, the owners (an American and Italian), are proud to say we strived to keep the apartment's old world charm during the restoration process. It paid off, as our home was ultimately featured Italian architectural magazine.. (Case di Campagna).

The fortress town dates back to 1198. Our second floor apartment (2 flights up to our front door) is part of the ancient walls of the medieval fortress. Remodeled some years back, the interior reflects the hamlet's old world charm while still offering 21st century comforts. The master bedroom (up a short flight of stone steps off the main room), offers an ensuite bathroom with shower. The intimate rooftop terrace and the room's bifora window truly grace our guests with a 360° view of Tuscany. The second bedroom, on the main level, offers the same enchanting view of Tuscany’s silvery olive groves and patchwork vineyards. This bedroom has been set up as a second master with a queen size bed. The bathroom, with its walk-in shower) is adjacent to the bedroom.

The main room is an open space, comprising a well-equipped kitchen alcove and a dining table that comfortably seats six (even twelve if opened). This dining/living area has two comfortable sofas and an armchair that makes into a single bed (if needed).

The owner, a Tuscan cookbook author, ensures guests will find everything they need to prepare a savory Tuscan meal in the apartment's fingertip kitchen. There is a traditional oven, microwave, four burner gas stove top and dishwasher. There is a washing machine in the apartment, a drying rack, iron and ironing board.

There is wifi throughout the apartment with 24 hour free access. There is also a television in the living area for those who want to brush up on their Italian by watching Italian news, flicks and variety t.v.!

The hamlet, a typical medieval cobblestone fortress town, boasts of two archways (one to enter the hamlet and one to exit). Built around the year 1198, the hamlet still boasts an enchanting medieval aire. Our property is located on the main cobblestone street midway between the two archways. Within the walls one will find three excellent restaurants, two wine bars, and a handful of shops. Outside the walls of the fortress (a two minute stroll), there are two banks with ATM machines, two coffee bars, two grocery stores (one with freshly baked goods daily), a pharmacy, a post office and more. There are buses running to and from Florence and Siena (55 minutes in either direction) from 6 a.m. until 7 p.m. weekdays and also a few on the weekends. Tickets must be purchased on-line or at the tabacchi in the nearby village of Tavarnelle Val di Pesa (2 km away).

The neighboring medieval towns of Certaldo Alto (quaint hilltop fortress) and San Gimignano (The Manhattan of Tuscany) are within a 20 minute drive of the property. There are numerous other quaint hilltop towns scattered around this enchanting region, known as Chiantishire to the English. We highly recommend renting a car to explore the area's many hidden treasures.

The nearest town to the hamlet is Tavarnelle Val Di Pesa. There is a lovely footpath connecting this modern village to Barberino Val D'Elsa. The path (lined with olive trees) is approximately 2 kms long. Point of interest: Tavarnelle has a lovely outdoor market on Thursday mornings from 8a.m. to 1 p.m. Great place to mingle with the locals and pick up organic veggies, shoes, trendy clothes and more.

So, if mingling with the locals in a sleepy fortress town in Tuscany while sipping wine in an enchanting little square is on your wish list, then Barberino and our flat is the perfect place to do just that.

We are always happy to supply additional information about the area to traveling guests (i.e. festivals, fairs, wineries to visit, art shows etc). Culinary workshops in the property or in Florence for those ‘foodies’ can also be arranged with advance notice. Ask about private dining with English speaking hosts in Florentine homes as well.

For those who wish to swim or sunbath during the summer, we are happy to direct you to two lovely outdoor pools with garden settings nearby. For a nominal entrance fee, one can spend a relaxing afternoon swimming or sunbathing while mingling with the locals.

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House Rules

Check in after 2:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 3–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number IT048017C2B9QQVYMF
Property # 3880312
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is no smoke detector on the property
Safety features at this property include a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Barberino Val d'Elsa

Located in Barberino Tavarnelle, this apartment is in a rural area. Castello di Barberino Val d'Elsa and Passignano Abbey are local landmarks, and some of the area's attractions include Chianti Observatory and Il Fiaschetto. Take some time off to enjoy the winery tours in the area, or get some fresh air with adventures like ecotours and horse riding nearby.
Map
Barberino Val D'elsa, Toscana

What's nearby

  • Santa Lucia al Borghetto Church - 10 min drive - 2.5 km
  • Ponte Vecchio - 48 min drive - 38.5 km
  • Piazza della Signoria - 48 min drive - 38.5 km
  • Uffizi Gallery - 48 min drive - 38.5 km
  • Piazza di Santa Maria Novella - 51 min drive - 36.9 km

Getting around

  • Barberino Val d'Elsa Station - 12 min drive
  • Peretola Airport (FLR) - 46 min drive

Restaurants

  • ‪Area di Servizio Drove Est - ‬10 min drive
  • ‪La Cantinetta di Rignana - ‬27 min drive
  • ‪Antica Trattoria La Toppa - ‬11 min drive
  • ‪La Taverna di Ciccino - ‬11 min drive
  • ‪Ristorante Borgo Antico - ‬4 min drive

Frequently asked questions

Is Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views?

As of 19 August 2026, prices found for a 1-night stay for 2 adults at Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views on 26 August 2026 start from NZ$1,473, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views?

On-site parking is available at the property.

What time is check-in at Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views?

Check-in begins at 2:00 PM.

What time is check-out at Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views?

Checkout is at 10:00 AM.

Where is Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views located?

Situated in a rural location, this apartment building is 2 mi (3.3 km) from Poggio al Bosco and 3.1 mi (5 km) from Sant'Appiano Parish Church. Castello di Barberino Val d'Elsa and Antinori nel Chianti Classico are also within 6 miles (10 km).

About the host

Hosted by Cindy Harding

Host profile image
Born and raised in California, I relocated to Tuscany in 1979 after meeting my Florentine husband on a vacation the year before.

I fell in love with Tuscany and especially Barberino Val D’Elsa. For an American, the village was a fairytale spot. I was bound and determined to own something in that fortress town. It took 10 years, but finally in 1989 a small tower property came up for sale. We bought it within 10 minutes of seeing it. It took nearly two years of restoration (binding laws, thick walls and slow workers) to finish our home. Initially it was to be our vacation spot. But, after the renovation I insisted we move in and live the authentic life of Tuscan villagers. And that we did for 4 years. Once our boys became of school age we moved to Florence where sports and school trumped the serene village life I preferred; keeping our small tower apartment in the Chianti wine region for our weekend retreat.

Although we live in Florence, the first sixteen years of my Italian life were spent in this region. The first twelve years in a two hundred year old farmhouse near the hamlet, then in the hamlet. Thanks to the women in this area (moms and grandmothers) who took me under their wings, I soon became a Tuscan mother myself. Knowing my passion for food and cooking, they shared their culinary secrets with me, shared their kitchens, and shared their stories. Once I relocated to the city, I decided to share my Tuscan life by writing a food memoire/recipe book in honor of what these ‘fine’ chefs taught me: Zucchini Blossoms -A Culinary Memoir & Recipes From Tuscany.

Why they chose this property

Set in a unique spot, the fortress town is surrounded by Tuscany’s patchwork vineyards and silvery olive groves. As a writer and lover of nature and history, I was swept away by the area and the hamlet's authenticity. So, in 1989 when this property came up for sale, I knew I had to have it. It took over two years to complete the restoration of the apartment. We were careful in keeping the authenticity of its architectural makeup but at the same time wanted to give it a bit of modernity.

What makes this property unique

The views from our master bedroom are simply breathtaking. Every time I open the bifora window in our bedroom, or walk out onto the cozy rooftop terrace, a smile crosses my lips... 'this is Tuscany,' I think. I am truly blessed to have relocated to this enchanting corner of the globe some four decades ago.

Languages:

English, Italian

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