Vacation rentals in Cupi

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Top-rated vacation rentals in Cupi

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Guest favorite

A scenic view captures a serene outdoor area featuring a turquoise swimming pool, surrounded by sun loungers and lush greenery. Rolling hills and fields stretch into the distance, complementing the clear sky adorned with soft clouds, creating a peaceful countryside atmosphere.

Farm stay in Manciano

4.98 out of 5 average rating, 66 reviews

Casa Olivia: Comfort, Nature and Landscapes of Maremma

Placed in the Manciano countryside, in the intact landscape of South Tuscany, 20 min from the Saturnia Cascades, Casa Olivia is an apartment in a farmhouse in the center of an age-old olive grove. From the garden and the house you can enjoy an incredible view on the Maremma hills with the Argentario coast in the background. Uncontaminated nature, peace and a wide choice of excursions in the surrounding area between art, history, sea and traditions. 30 minutes from beaches and beautiful villages

Superhost

A charming exterior of the villa is displayed, featuring a pink stucco facade and green shutters. A tiled terrace is visible in front, surrounded by greenery. The view of the sea is unobstructed, and the inviting entrance door suggests easy access.

Condo in Porto Santo Stefano

4.88 out of 5 average rating, 208 reviews

Charming apartment with breathtaking sea views

Charming apartment with breathtaking sea views. The property includes a spacious kitchen, a bathroom, a bedroom with a double bed, a second bedroom with two single beds that can also be used as a living room, and a terrace equipped with a table and loungers: perfect for relaxing with a stunning sea view! Spacious wardrobe closet in each room, fiber optic Wi-Fi, air conditioning, a large private parking area and a private shortcut that connects directly to the town (just a 5/10 minute walk away).

Top guest favorite

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage in Geggiano

4.99 out of 5 average rating, 135 reviews

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.

Guest favorite

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

4.91 out of 5 average rating, 216 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Top guest favorite

An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.

Guesthouse in Montefollonico

4.97 out of 5 average rating, 105 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Top guest favorite

A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.

Home in Castellina in Chianti

4.98 out of 5 average rating, 116 reviews

StageROOM03 -Chianti Idillic Country living

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favorite

A serene outdoor view captures a private swimming pool framed by neatly manicured grass. Lush cypress trees line the background, against a vibrant sunset sky displaying hues of orange, pink, and purple, creating a calming ambiance in the countryside.

Home in Pereta

5 out of 5 average rating, 63 reviews

Bel Casale with sea view and the mediaeval village

In the Maremma countryside, private panoramic swimming pool, with a 360° !!! View of the Argentario, the island of Giglio and the medieval village. Spectacular sunsets to admire! The villa is on one floor, characterized by exposed wooden beams, verandas, handmade terracotta floors, elegant minimal furniture. It can accommodate up to 6 people. Park of 2 hectares of garden with olive grove and centuries-old oaks. Located 5 minutes from the beautiful village of Pereta.

Guest favorite

The open-plan dining area features a round wooden table surrounded by six wooden chairs. A sleek kitchen is visible with minimalist cabinetry and modern appliances. Soft lighting illuminates the space, highlighting the high ceilings and natural materials of the walls.

Apartment in Montemerano

5 out of 5 average rating, 13 reviews

[Luxury Apartment] “Saturnia Next”

Situato a Montemerano, uno dei borghi più belli d’Italia, a pochi minuti dalle celebri Terme di Saturnia, l'appartamento gode di una posizione strategica, ideale per chi desidera relax e bellezza. Saturnia Next si distingue per lo stile elegante e ricercato, arricchito da dettagli curati e opere d’arte che raccontano gusto e raffinatezza. Il vero gioiello della casa è il terrazzino panoramico, da cui si apre una vista mozzafiato sulle dolci colline della Maremma.

Top guest favorite

A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.

Home in San Quirico d'Orcia

4.99 out of 5 average rating, 212 reviews

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Superhost

A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.

Condo in Castelnuovo dell’Abate

4.91 out of 5 average rating, 293 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Top guest favorite

A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.

Loft in Siena

4.95 out of 5 average rating, 239 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town