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59 Holiday apartments & homes for a holiday with your dog in Maremma

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Boccheggiano

Podere Pozzuolo

6 guests

95 m²

3 bedrooms

7 reviews

Free cancellation

Sustainable

The apartment is a beautiful stone house. Quiet idyllic location between forests and fields for nature lovers. Ideal for families with children, pets allowed.

Free cancellation

Sustainable

from 58 € per night / night

4.5

prices from 59€ per night

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Caldana

Casa Bomberto

4 guests

100 m²

2 bedrooms (+1)

41 reviews

Especially sustainable

Romantic, newly renovated cottage, absolutely unique location situated in a forest Maremma - large garden, cozy terraces, Dogs and cats welcome!

Especially sustainable

from 75 € per night / night

4.9

prices from 75€ per night

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Marina di Grosseto

Il Bramasole

6 guests

68 m²

2 bedrooms

5 reviews

RESERVE NOW FOR 2026! Beautiful and affordable holiday home with pool by the sea Maremma 4-6 people - large fenced garden, dogs welcome!

from 112 € per night / night

4.8

prices from 112€ per night

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Campagnatico

Villa Ombrone

6 guests

160 m²

3 bedrooms

Dreamlike and comfortable holiday villa with heated pool, panoramic terrace, fitness room, sauna

from 378 € per night / night

prices from 379€ per night

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10%

Giuncarico

Charmantes Ferienhaus Giuncarico

6 guests

100 m²

2 bedrooms

10% Last-Minute 07/27/2026 - 08/03/2026

Charming holiday home Giuncarico: 100 m², 6 people, garden, village pool, only 24 km from the sea

10% Last-Minute 07/27/2026 - 08/03/2026

from 86 € per night / night

prices from 86€ per night

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Arcille

Holiday home relaxing holiday Arcille

6 guests

90 m²

2 bedrooms

1 review

from 100 € per night / night

4.6

prices from 101€ per night

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Roselle

Casa Plinio Apartment

6 guests

70 m²

2 bedrooms

6 reviews

Apartment for 4-6 people with swimming pool, 20 km from the sandy beaches at Marina di Grosseto, 2 bedrooms Garden, Terrace

from 74 € per night / night

4.6

prices from 74€ per night

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Boccheggiano

Villa Lia

8 guests

140 m²

4 bedrooms

1 review

Free cancellation

Sustainable

Free cancellation

Sustainable

from 176 € per night / night

5.0

prices from 177€ per night

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Caldana

Casa Poggio

6 guests

80 m²

2 bedrooms

10 reviews

from 83 € per night / night

5.0

prices from 84€ per night

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Roccastrada

Casa Mauro with private pool

9 guests

150 m²

4 bedrooms

Luxurious natural stone villa with large swimming pool 15 x 4 m x 1.30 m deep for 2 - 9 people.

from 533 € per night / night

prices from 534€ per night

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Roccatederighi

Casa Dora - privater Garten, Pool

5 guests

80 m²

3 bedrooms

from 60 € per night / night

prices from 60€ per night

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10%

Orbetello

Holiday home relaxing holiday Orbetello

4 guests

36 m²

2 bedrooms

2 reviews

10% Promotion 09/05/2026 - 09/20/2026

from 162 € per night / night

4.4

prices from 162€ per night

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10%

Ferienhaus Modernes Rustico Traumblick Maremma

Ribolla

Ferienhaus Modernes Rustico Traumblick Maremma

4 guests

125 m²

2 bedrooms

Sustainable

10% Early-Bird 04/10/2027 - 05/01/2027

Modern dream house near Ribolla in the hills of Maremma. Unique location with a great view to the island of Giglio and tranquility amidst an olive grove.

Sustainable

10% Early-Bird 04/10/2027 - 05/01/2027

from 149 € per night / night

prices from 149€ per night

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Roccastrada

Casa Mauro with private pool

4 guests

50 m²

2 bedrooms

6 reviews

Holiday house for 2-4 pers. with pool

from 74 € per night / night

4.8

prices from 74€ per night

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Massa Marittima

Wohnung "Campo del Conte"

4 guests

90 m²

1 bedroom

Apartment "Campo del Conte" in Massa Marittima: 90 m², 1 room, accommodates up to 4 people.

from 60 € per night / night

prices from 60€ per night

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Roccastrada

Holiday flat family holiday Roccastrada

6 guests

60 m²

2 bedrooms

from 43 € per night / night

prices from 44€ per night

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Roccastrada

Casa Mauro with private pool

6 guests

54 m²

2 bedrooms (+1)

Holiday house for 2-4 pers. with pool

from 71 € per night / night

prices from 71€ per night

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Orbetello

Holiday home relaxing holiday Orbetello

4 guests

40 m²

1 bedroom (+1)

5 reviews

from 119 € per night / night

4.9

prices from 119€ per night

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Ribolla

Casa Casteani with Pool

5 guests

80 m²

2 bedrooms

2 reviews

2 Apts. with pool for 4-12 pers. 22 km to the sea

from 105 € per night / night

4.9

prices from 106€ per night

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Roccatederighi

Scoiattolo + Riccio

4 guests

40 m²

2 bedrooms

Holiday house with pool for 2-4 pers

from 71 € per night / night

prices from 71€ per night

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Massa Marittima

Villa with panoramic view and pool

6 guests

120 m²

4 bedrooms

- Comfortable stone house, finished in 2017 - Absolute peace, absolute peace in nature, wonderful view - Pool directly in front of the house, 30 minutes to the sea -

from 184 € per night / night

prices from 184€ per night

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Orbetello

Holiday home relaxing holiday Orbetello

4 guests

31 m²

1 bedroom (+1)

2 reviews

from 99 € per night / night

4.8

prices from 99€ per night

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Orchideenfarm mit 3 Wohnungen und Pool bei Montemassi

Roccastrada

Orchideenfarm mit 3 Wohnungen und Pool bei Montemassi

4 guests

42 m²

1 bedroom

3 holiday apartments near Montemassi, each for 4 people, 42m², 1 bedroom, private terrace, pool.

from 61 € per night / night

prices from 61€ per night

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Casa Carla mit Privat-Pool in Panorama-Alleinlage

Roccastrada

Casa Carla mit Privat-Pool in Panorama-Alleinlage

10 guests

130 m²

5 bedrooms

Holiday home Casa Carla with private pool, secluded location in Roccastrada, Tuscany, 130m² for up to 9 people.

from 207 € per night / night

prices from 207€ per night

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Arcille

Holiday home relaxing holiday Arcille

9 guests

220 m²

4 bedrooms

from 167 € per night / night

prices from 168€ per night

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Guest reviews of our holiday apartments in Maremma

5.0

Verified guest from Tourist-paradise.com

Casa Bomberto

Caldana

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Without any problems and always very gladly again!

The town of Caldana, like many in Tuscany, is located on a hill with a beautiful old town, an impressive view of the surroundings, and a thriving and open village life. The people here are very friendly and seem to be happy. The village shops offer everything you need for your daily needs.

The accommodation is a matter of the owners' hearts. Since 2016, we have been able to spend our holidays there. From year to year, investments are made in technology, appearance, and equipment, and a lot of work and passion flow into the property. A reliable infrastructure and a secure water supply from the private well are not self-evident in this area, but they are here.

The "Casa Bomberto" is not a typical rental property, but a realized life-long dream of the owners that every guest can be a part of. The landlords are very open, warm, and friendly, and always available and helpful. The equipment far exceeds what is necessary.

The holiday experience
In complete tranquility, everyday life is quickly forgotten. The soul devotes itself to other things like the sunrise through the adjacent trees, the sounds and scents of the forest. The house and garden offer a perfect ambiance to enjoy the area and its culinary specialties and to completely relax.

The access road is often criticized, but ultimately it is not a real problem. The width of the paths is completely sufficient, and there is now a drainage system in place. The route is mostly covered with gravel and crushed stone. Only at two points do tree roots or flat stones protrude, where it is advisable to drive at a slow speed. But that doesn't bother the car - your vehicle can handle it, even without all-wheel drive. For someone who knows and controls their vehicle, it can even be fun.

from 75€ night

4.8

Casa Poggio

Caldana

View German

Tuscany like a picture book

We (family with 5-year-old twins) had two wonderful weeks in Casa Poggio and felt very comfortable in Caldana. There is nothing missing in the house, everything you need is there. Due to the elevated level of the house, you are comfortably alone on the terrace, so that you can end the evenings there perfectly. The village of Caldana itself is also wonderful. A supermarket is only 5 minutes away. The main street with restaurants (here we can highly recommend Il Borgo. Very tasty pizza, but also very tasty fish and pasta dishes) and pizza to go is only 10 min away. What makes Casa Poggio special, however, is the fact that we have never before met such friendly and caring landlords. Starting with a rebooking of the holiday originally planned for 2020 to 2021, which was necessary due to the Corona pandemic, but without any problems, continuing with a large number of very friendly telephone calls, and ending with the lovingly designed travel instructions that every tenant receives in advance by e-mail. Simply great. And how could it be otherwise, we are already very much looking forward to returning in the summer of 2022. Once again, a heartfelt thank you and many warm greetings to the landlord family

P.S.: The only small point deduction for the location is only due to the fact that you have to plan at least a 20-minute drive to get to the sea. You just have to take that into account when planning, but again, the wonderful travel tips help here, as they already present a great selection of possible beaches. We personally chose the beach between Castiglione della Pescaia and Grossetto di Marina, also because of our children who are not yet swimmers. From the car park there, after a short walk through a typical pine forest, you reach a long sandy beach with very slowly deepening water. Perfect for families.

from 84€ night