
Holiday rentals with a pool in Grosseto
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Grosseto
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.
4.93 out of 5 average rating, 145 reviews
Elegant farmhouse Siena
The 200-square-meter apartment is part of a 17th-century farmhouse: it comfortably accommodates 6 people, has 3 large bedrooms, a princely living room, a kitchen with a fireplace, two bathrooms, and a breathtaking view of the Tuscan countryside up to Montalcino. As of April 1, 2025, the Municipality of Murlo will charge a tourist tax of €1.50 per person per day. Children under 12 years of age are exempt. The tax must be paid upon arrival in cash, and your passports will be requested at the same time.
4.96 out of 5 average rating, 168 reviews
Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
4.97 out of 5 average rating, 126 reviews
Casa Mirta art & nature in the heart of Maremma
We welcome you in one of the most beautiful landscapes of Italy, in the countryside between Capalbio and Montemerano. Mirta is an apartment in the casale located in the center of a centuries-old olive grove. The garden offers an incredible view on the Maremma hills with the Argentario coast in the background. Uncontaminated nature & silence and a wide choice of excursions in the surroundings with art, history, borghi and traditions. 20 minutes from Saturnia and 30 from the beaches of Capalbio
4.96 out of 5 average rating, 114 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 reviews
Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * 2 AirCon units: 1 per bedroom * * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *
4.92 out of 5 average rating, 148 reviews
EcoLodge – modern design in a peaceful panoramic location
The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.
4.94 out of 5 average rating, 111 reviews
Mimosa Apartment - Poggio al Vento
Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc
4.99 out of 5 average rating, 112 reviews
Tuscan Barn Apartment for 6 with panoramic pool
Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.
4.89 out of 5 average rating, 100 reviews
"L'Assolata" Cottage in Tuscany
A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).
4.91 out of 5 average rating, 157 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.
4.95 out of 5 average rating, 104 reviews
Spedaletto Castle, Val d'Orcia, Pienza
The Castello di Spedaletto farmhouse is located in the building that once housed the granary of the ancient medieval castle and has been recently renovated in perfect balance between modernity and tradition: stone, bricks, exposed beams blend with the characteristic crystal and wrought iron staircase. The farmhouse consists of 5 double bedrooms with bathrooms and 2 apartments. Come, See, Live...
4.97 out of 5 average rating, 185 reviewsPopular amenities for Grosseto rentals with a pool
House rentals with a pool

Country House in the Crete Senesi
4.97 out of 5 average rating, 210 reviews
Lovely home in villa with garden and pool
4.8 out of 5 average rating, 153 reviews
Stunning new house with amazing sea view and pool
4.81 out of 5 average rating, 57 reviews
Vetulonia farmhouse with a relaxing pool
4.95 out of 5 average rating, 60 reviews
La Capanna: country house with magnificent view
4.92 out of 5 average rating, 85 reviews
Argentario: Villa Volo Pindarico
4.83 out of 5 average rating, 6 reviews
The little house in the banditelle
5.0 out of 5 average rating, 25 reviews
S.Ilaria - Private pool Villa with 2 bedrooms
4.97 out of 5 average rating, 96 reviewsCondo rentals with a pool

Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 97 reviews
Infinity pool overlooking the woods, sea just minutes away
5.0 out of 5 average rating, 53 reviews
Holiday in an antique farm, The Arches
4.86 out of 5 average rating, 22 reviews
Podere Cupiano "La Costa"
4.99 out of 5 average rating, 69 reviews
Borgo 7 Tigli | King Suite & Tuscan Views
4.67 out of 5 average rating, 3 reviews
Studio apartment
4.96 out of 5 average rating, 24 reviews
Apartment in ancient house + pool and terrace
4.95 out of 5 average rating, 19 reviews
Poggio ai Gelsi, Melograno Lodge
4.82 out of 5 average rating, 60 reviewsOther holiday rentals with a pool

A paradise in Montepulciano...
4.96 out of 5 average rating, 168 reviews
Suite, private apt for 2/4, pool
4.95 out of 5 average rating, 104 reviews
Podere la Pompa
5.0 out of 5 average rating, 27 reviews
Agriturismo Marrucheti 82 South Apartment
5.0 out of 5 average rating, 46 reviews
Agriturismo Bandinelli #3 "Palmizia"
4.94 out of 5 average rating, 65 reviews
Stone villa with pool
5.0 out of 5 average rating, 23 reviews
Villa Marsiliana
4.92 out of 5 average rating, 26 reviews
Fonte dei Frati - Private Villa and Pool
4.98 out of 5 average rating, 58 reviewsDestinations to explore
- Private suite rentals Grosseto
- Tent rentals Grosseto
- Rentals with a kayak Grosseto
- Hotel rooms Grosseto
- Villa rentals Grosseto
- Loft rentals Grosseto
- Serviced apartment rentals Grosseto
- House rentals Grosseto
- Family-friendly rentals Grosseto
- Farmstay rentals Grosseto
- Guesthouse rentals Grosseto
- Rentals with a sauna Grosseto
- Rentals with breakfast Grosseto
- Boutique hotels Grosseto
- Apartment rentals Grosseto
- Bed and breakfasts Grosseto
- Tiny house rentals Grosseto
- Rentals with beach access Grosseto
- Pet-friendly rentals Grosseto
- Waterfront rentals Grosseto
- Holiday home rentals Grosseto
- Castle rentals Grosseto
- Cottage rentals Grosseto
- Condo rentals Grosseto
- Rentals with lake access Grosseto
- Rentals with a hot tub Grosseto
- Luxury rentals Grosseto
- Townhouse rentals Grosseto
- Beachfront rentals Grosseto
- Rentals with an accessible height bed Grosseto
- Rentals with pools Tuscany
- Rentals with pools Italy
- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Capo Bianco
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- La Scarzuola
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Necropolis of Tarquinia
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Things to do Grosseto
- Food tours Grosseto
- Outdoors Grosseto
- Tastings Grosseto
- Cooking Grosseto
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
- Food tours Tuscany
- Shopping and fashion Tuscany
- Dining Tuscany
- Performances Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy





