
Pet-friendly holiday rentals in Massa Marittima
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Top-rated pet-friendly home rentals in Massa Marittima
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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

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with all the families in this home. The farmhouse consists of two independent apartments with a living room, kitchen, bedroom and bathroom. You will not have to share anything with the other guests, as we have arranged everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. Nearby Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

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.

Il Frantoio - Charming Loft in the old town
This elegant and spacious Loft “Il Frantoio”, with a living area of 160 m², is located in the old town of the medieval village Radicondoli. The open space kitchen and livingroom area is designed to give a high comfort and reminds us the ancient function of this bluilding that was the oil mill of the comunity. The Loft was recently completly restored with a high focus on comfort and best quality materials.

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!

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Stunning Tuscan apartment for 2
This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.
Popular amenities for Massa Marittima pet-friendly home rentals
Pet-friendly house rentals

Casa Al Poggio & Chianti view

The charming cottage in Tuscany with breathtaking views

Podere Piazza house with panoramic view

Casa Dante

Jenny's Barn

Casa Pancole

Tuscan cottages in an ancient villa with a garden

Eleutherìa: Cozy Cottage in the heart of Tuscany
Pet-friendly home rentals with a pool

Belforti Tower

San Giovanni in Poggio, villa Meriggio 95mq

Suggestivo Ex fienile agriturismo Maremma Toscana

Explore nature in the center of Vigneti Chianti

country villa with heated swimming pool

Gelsomino Apartment in Agriturismo with Pool

Casa Olivia: Comfort, Nature and Landscapes of Maremma
Wp Relais Villa Vignalunga
Private, pet-friendly home rentals

Private villa in Maremma 15 minutes from the sea

House with private terrace and countryside view

I Tramonti di Eramo, Montepulciano city center.

La Casetta di Brunello, very panoramic with terrace

Casa del Poggio, with a beautiful sea view

La Dolce Vita Romantic Sea-view Cottage. Tuscany
La Piazzetta - Cozy open space in the historic center of Montepulciano

La Conchetta – Bolgheri
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $120 SGD | $120 SGD | $128 SGD | $143 SGD | $130 SGD | $140 SGD | $135 SGD | $164 SGD | $135 SGD | $125 SGD | $124 SGD | $121 SGD |
| 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 |
Quick stats about holiday rentals that are pet-friendly in Massa Marittima

Total holiday rentals
Explore 50 holiday rentals in Massa Marittima

Nightly prices starting at
Massa Marittima holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 380 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Massa Marittima holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Massa Marittima rentals

4.7 Average rating
Massa Marittima stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Pet-friendly rentals Grosseto
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- Elba
- Giglio Island
- Marina di Cecina
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- Siena Cathedral
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- Feniglia
- Cala Violina
- Cattedrale di San Francesco
- Gulf of Baratti
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- Le Cannelle
- Palazzo Pubblico
- Santa Maria della Scala
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- Arcipelago Toscano National Park
- Ugolino Golf Club
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- Abbey of Monte Oliveto Maggiore




