Vacation rentals in Fratta-Santa Caterina

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Top-rated vacation rentals in Fratta-Santa Caterina

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

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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

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

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4.9 out of 5 average rating, 241 reviews

Guest favorite

Condo in Fratta-Santa Caterina

Cortona – Pool & Relaxation among Olive Trees|Adults Only+16

Nestled in the Tuscan countryside, this apartment is designed for adult guests (+16) looking for silence, privacy, and relaxation. 15 minutes from the A1 Valdichiana (Bettolle-Sinalunga) tollbooth and 7 km from Cortona, it is part of a private property in the countryside, ideal for visiting villages and wineries. Outdoor space, panoramic pool and private parking to relax outdoors. Equipped kitchen and bright relaxation area. Excellent base for Valdichiana, Lake Trasimeno, Montepulciano and Pienza.

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5.0 out of 5 average rating, 8 reviews

Top guest favorite

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

LocationFamilyBathroom

4.97 out of 5 average rating, 252 reviews

Top guest favorite

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

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4.92 out of 5 average rating, 338 reviews

Top guest favorite

Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.

Farm stay in Montepulciano

Tuscan farmhouse stay with restaurant and pool

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

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4.94 out of 5 average rating, 109 reviews

Top guest favorite

An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.

Villa in Cortona

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

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5.0 out of 5 average rating, 96 reviews

Top guest favorite

Home in Castiglion Fiorentino

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

FamilyValueNearby

5.0 out of 5 average rating, 23 reviews

Top guest favorite

A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.

Condo in Cortona

Chicca: Cortona's historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

ValueFamilyCondition

4.98 out of 5 average rating, 225 reviews

Top guest favorite

Vacation home in Petrignano

Fontarcella, H&R- mediterranean home with jacuzzi

Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.

ValueLocationCleanliness

4.98 out of 5 average rating, 169 reviews

Guest favorite

A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.

Home in Foiano della Chiana

Conca d'Oro villa with private pool, sleeps 4

Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 173 reviews

Guest favorite

The spacious living area features exposed wooden beams and brick arches, with a warm-toned terracotta floor. A wooden table and chairs are visible, alongside a cozy seating arrangement in yellow fabric. Natural light enters through large windows, enhancing the inviting ambiance.

Apartment in Fratta-Santa Caterina

Charming apartment with small gardens, pool access

Discover a charming ground floor one-bedroom apartment near Cortona, featuring a spacious living area, a fully equipped kitchen, and two private gardens—one with a covered gazebo for shade. The apartment is part of small residence and has its own private entrance. Guests can enjoy access to a shared swimming pool (open June 15 – September 15) and two private parking spaces. A perfect retreat for relaxation and exploring the beauty of Tuscany.

LocationFamilyCheck-in

4.87 out of 5 average rating, 30 reviews

Top guest favorite

The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.

Home in Cortona

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

FamilyValueView

4.94 out of 5 average rating, 225 reviews