
Holiday houses in Massa Marittima
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Top-rated holiday rentals in Massa Marittima
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Casa Vecchio Forno
The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from the Cathedral square. It is easily accessible from all the parking lots in the historic center and within walking distance you can find: cafes, restaurants, banks, grocery stores, a pastry shop and a pharmacy. The recently renovated 68m house has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

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.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for Massa Marittima holiday rentals
Other great holiday rentals in Massa Marittima

The house in the Castle and the secret garden

AnticaVista, Luxury Apartment with Tower Views

Apartment in a wine estate

Rosa: Tuscan Views & Pool, Walk to Town

Villa Torre di Tignano @Luxury Retreat in Chianti

The pomegranate, Podere il Giglio

Gelsomino Apartment in Agriturismo with Pool

The twigs
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $137 NZD | $154 NZD | $147 NZD | $166 NZD | $170 NZD | $173 NZD | $182 NZD | $199 NZD | $189 NZD | $149 NZD | $153 NZD | $151 NZD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Massa Marittima?
Yes! Work meets play with ease at over 40 vacation rentals in Massa Marittima featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Massa Marittima vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Massa Marittima, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Massa Marittima?
Experience the best of Massa Marittima with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Massa Marittima?
Four-legged friends are welcome in Massa Marittima. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Massa Marittima?
Massa Marittima has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Massa Marittima have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Massa Marittima?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with wifi, over 60 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Massa Marittima have wifi?
Absolutely! We offer over 50 apartment rentals with wifi in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Massa Marittima have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Massa Marittima have a kitchen?
Absolutely! We offer over 60 apartment rentals with a kitchen in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Massa Marittima

Total holiday rentals
Explore 110 holiday rentals in Massa Marittima

Nightly prices starting at
Massa Marittima holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 1,880 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Massa Marittima holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Massa Marittima rentals

4.8 Average rating
Massa Marittima stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Elba
- Giglio Island
- Spiagge Bianche
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Libera
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Spiaggia Marina di Cecina
- Cala di Forno
- Spiaggia di Marina di Campo
- Spiaggia Zuccale
- Castiglion del Bosco Winery
- Spiaggia di Patresi
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Cavo
- Spiaggia di Marina di Grosseto
- Spiaggia Verruca




