
Apartment holiday rentals in Roccastrada
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Roccastrada
Guests agree: These apartments are highly rated for location, cleanliness and more.

La Sorpresa Studio Apartment
Studio apartment in the heart of Pitigliano, a short walk from the Synagogue and the Etruscan Vie Cave. The apartment offers a beautiful view of the Meleta valley. It is carefully furnished with antique and valuable furniture and objects. It offers a smart working station. The house is located in the center of Pitigliano, just a few meters from the Synagogue and the “Etruscan hollow streets”. It offers an amazing view of the Meleta Valley. The apartment is furnished with care and with fine antiques.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

House of Delights - The Medici private leisure house
La Casa di Delizie, a luxurious retreat nestled in a historic guard tower dating back to the Middle Ages, once cherished by the Medici family. Adorned with the exquisite fresco "Caduta di Icaro," this exclusive apartment seamlessly blends rich history with contemporary luxury. Ideally located on Via Orti Oricellari, just 150 meters from the main train station, it provides effortless access to Florence's treasures. Indulge in bespoke experiences and refined amenities for an unforgettable escape!

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

The Cellar (Palazzo Pallotti)
The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

“La Vittoria” House
Mine is a beautiful apartment for exclusive use in the center of Monticchiello. Equipped with every comfort, fully equipped kitchen. Linens. Bright living room and two comfortable bedrooms, one of which overlooks one of the main squares of the village and enjoys views of the Val d'Orcia and Mount Amiata. A stone's throw from my Ristorante Daria, one of the best in the area where you can taste good traditional dishes revisited impeccably. I look forward to seeing you! Deborah

Casa Sabina
The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Villa di Geggiano - Perellino Suite
The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

I Tramonti di Eramo, downtown Montepulciano.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

The Enchantment of Civita (The Terrace)
L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Theater House
Casa teatro is an elegant apartment located inside a prestigious building in the heart of Orvieto's historic center, a few steps from Piazza del Popolo and the city's most important tourist sites. The apartment is stylishly furnished, bright, characterized by ceilings and walls with frescoes attributed to the famous 19th-century painter Andrea Galeotti.

"Red Rose" apartment with view of Siena.
Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).
Popular amenities for Roccastrada apartment rentals
Weekly apartment rentals

Tuscany jem: The Chianti Farmer's House

Bruna's House

Romantic cottage with panoramic view

Cortona Shabby Chic House - independent & balcony-

Apartment with panoramic garden in San Gimignano

La Dimora del Luca

Wonderful house with garden

La Violetta di San Quirico, Historic Center.
Private apartment rentals

Elegant historic Palazzo, views of Tuscan valley

Penthouse in small medieval castle near Florence

NiKKO 119 [Loft Deluxe With Garden City Center]

Vicolo Porte 21/23, Massa Marittima, Jacuzzi

Live Like a Local & Private Concierge Service

Luxury Penthouse with Incredible View & A/C 300mq

Herons Superior Apartment - Splendid view!

Tenuta di Montemassi Azzurro Apartment for 2/3 people
Apartment rentals with a hot tub

Iris apartment [5 min downtown] Suite with Jacuzzi

At the top faboulous terrace Florence

Japan Apartment Port Area with Balcony and Jacuzzi

Charming House in Montepulciano

Nadja's Home with hot tub - perfect for couples

Domus Nannini - L'Arco di Matteotti Spa

Luxury frescoed apartment in the historical center

Cherubini Palace Thematic Apartments "TIME"
Destinations to explore
- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Del Chianti
- Spiaggia Di Sansone
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Le Cannelle
- Avignonesi Winery Fattoria Le Capezzine
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- CavallinoMatto
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Terme San Filippo
- Casa Vasari
- Abbey of Sant'Antimo





