Villa vacation rentals in Castiglione della Pescaia

Find and book unique villas on Airbnb

Top-rated villa rentals in Castiglione della Pescaia

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Villa in Siena

4.8 out of 5 average rating, 267 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Superhost

A sun-drenched terrace offers a view of the sea, bordered by well-maintained gardens featuring colorful flowers. A dining table with chairs sits on the stone patio, complemented by two lounge chairs. The rustic villa's wooden doors provide access to the interior.

Villa in Talamone

4.9 out of 5 average rating, 68 reviews

Villa Il Molinaccio with terrace and private beach

Spacious rustic villa with a terrace overlooking the sea and access via stairs to a small pebbly beach. Ample outdoor and indoor spaces with garden. It has sun beds, sun umbrella, table tennis and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the harbour and centre, offering privacy but accessibility to all amenities like beaches, windsurfing, diving, and boat hire. Private garage in front of the house on private road. Recently renovated. Vintage and maritime style.

Superhost

A serene pool area features a clear blue swimming pool surrounded by lush greenery and blooming flowers. A natural stone waterfall adds a calming element, while nearby, vibrant plants line the edges, enhancing the peaceful outdoor setting.

Villa in Castelnuovo Berardenga

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Superhost

The rustic villa is surrounded by lush greenery, offering a serene landscape. Its terracotta roof complements the natural setting, while pathways are lined with shrubs and trees. An inviting courtyard can be seen, creating a peaceful entrance to the home.

Villa in Castelnuovo Berardenga

4.89 out of 5 average rating, 9 reviews

Elegant Chianti Villa w/ Stunning Views + Starlink

Villa Adagio, in the compound of Casale Fornaci, is a magnificent country house inside the beautiful Tenuta of Arceno in the Chianti Classico. Surrounded by a grove of olive trees atop lush green hillsides, this 13th-century restoration with its terracotta floors, wood-beamed ceilings, and stone walls is the perfect vacation villa for families and friends wanting to enjoy Tuscan life at its finest. Enjoy memorable day trips to Florence, Siena, wineries & more.

Guest favorite

An entrance hallway is shown, featuring a wooden sideboard with ornate details, and a vintage vase filled with fresh flowers. Framed artwork is displayed on the walls, and a patterned rug adds warmth to the polished wooden floor.

Villa in Pergine Valdarno

4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

Villa Chiara is 210 sqm , almost entirely on one level . There is a spacious living room with a fireplace and adjacent dining room. A small studio, three double bedrooms , one single , and one large single. Three bathrooms and a large kitchen. A den with another fireplace leads up to the second floor where one of the doubles, and the single share a bathroom. Outside is a large covered terrace where you can eat alfresco,facing west, with long views.

Superhost

A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.

Villa in Radicondoli

4.94 out of 5 average rating, 18 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Superhost

A spacious outdoor patio features comfortable lounge chairs and a woven seating arrangement, overlooking lush, rolling hills. Natural greenery frames the view, contributing to a peaceful setting under a clear blue sky.

Villa in Montescudaio

4.8 out of 5 average rating, 10 reviews

PRIVATE VILLA BERTI TUSCANY FOREVER Montescudaio

Villa Berti TUSCANY FOREVER. This is standalone, new villa with private swimming pool and 3 bedrooms and 2 bathrooms. WE KNOW WHERE HAPPY KIDS ARE ! TUSCANY FOREVER featuring unique family friendly properties. Berti is located 2km from the center of Montescudaio town with magnificent views. Etruscan coast , the sea is about 10km away. If you’re facing an issue that requires a personal touch, please contact us.

Superhost

An oversized saltwater pool is showcased, surrounded by a stone patio and eight lounge chairs. Lush green hills and vineyards stretch into the distance, with clear blue skies above. The area is accented by well-maintained gardens and natural vegetation, enhancing the scenic landscape.

Villa in Castiglione d'Orcia

5 out of 5 average rating, 10 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

With outstanding 360 degree views of vibrant olive groves, cypress trees, and endless vineyards, this outstanding villa sits on top of the world. Surrounded by lush, rolling green hills, one of the most unique getaway experiences awaits. Equipped with a large saltwater pool and a modern interior with just the right amount of Tuscan flair, immerse yourself in the old country with a few added luxuries.

Superhost

A spacious living area is highlighted by exposed wooden beams and terracotta flooring. Natural light floods through large windows, adorned with soft curtains. An ornate wooden cabinet and decorative plants enhance the cozy feel, while a colorful rug adds warmth to the inviting atmosphere.

Villa in Asciano

5 out of 5 average rating, 4 reviews

Villa Le Liscaie [Sienese Crete]

Private Villa in the Crete Senesi - Stunning swimming pool surrounded by olive grow - 4 bedrooms: one master bedroom, one room with two single beds, one with a single bed and another room with a comfortable double sofa bed - large outdoor space and private forest - 5 minutes from the highway

Guest favorite

The historic villa displays a vibrant yellow façade, flanked by lush greenery and cypress trees. An inviting infinity pool is visible in front, surrounded by a stone patio. A shaded seating area offers a relaxing retreat near the steps leading to the entrance.

Villa in Greve in Chianti

4.92 out of 5 average rating, 25 reviews

Luxury villa in Tuscany Panzano in Chianti

Luxury villa surrounded by vineyards in walking distance from Panzano in Chianti. Infinity pool, pizza oven, pétanque area, outdoor fitness and breathtaking views over the rolling hills of Tuscany. The villa also has its own winery and produces both red and sparkling wine of high quality.

Guest favorite

A green lawn stretches out towards a stone wall, flanked by vibrant flowers in full bloom. Beyond the wall, rolling hills and trees create a serene landscape under a clear blue sky.

Villa in Bucine

4.96 out of 5 average rating, 23 reviews

Charming property, wi-fi, weddings ,cooking class

At the end of a long cypress-lined driveway, in a landscape little changed over the centuries you will find a perfect escape and hideaway of the private estate with two villas and with the chapel. The villas are a well-balanced blend of comfort and Tuscan tradition.