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Vacation rentals in Cortona

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Top-rated vacation rentals in Cortona

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

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Top guest favorite
The exterior of the house is depicted, featuring a two-story structure with a light yellow facade and brown shutters. Lush greenery surrounds the building, including tall trees and flowering plants. A pathway leads to the home against a backdrop of a blue sky with scattered clouds.
Home in Cortona
4.95 out of 5 average rating, 108 reviews

Casa Lucy

House located on the Cortonese hill, completely renovated, consisting of 3 double bedrooms, 2 bathrooms and an open space kitchen and dining room. It is located 5 minutes from the historic center of Cortona and in an excellent position to reach the most beautiful and characteristic places of Tuscany and Umbria such as Pienza, Montepulciano, Castiglione del Lago up to cities that are cradles of art such as Florence, Arezzo, Siena and Perugia. Mandatory tourist tax to be paid on site (€2.50 per person for 4 days)

ValueFamilyHiking

Top guest favorite
A spacious bedroom features a king size bed adorned with light bedding, complemented by decorative pillows. A chair is positioned near the window, which opens to a small private terrace with greenery visible. Iroko wooden parquet flooring adds a warm touch.
Apartment in Cortona
4.99 out of 5 average rating, 187 reviews

Cortona’s Rooftop Nest

The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It accommodates 4 people. Fans in the bedrooms The apartment is located in the historic center right in front of the wonderful church of St. Francis and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can accommodate up to 4 people. Fans in the rooms.

LocationFamilyLayout

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
4.9 out of 5 average rating, 240 reviews

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

ValueFamilyView

Top guest favorite
A window with multiple panes opens to reveal views of the stunning Piazza Signorelli and its historic buildings. Sunlight streams in, highlighting the charming architecture of the opposite structure, which features decorative arches and outdoor seating areas.
Vacation home in Cortona
4.89 out of 5 average rating, 106 reviews

Theater House

Cozy apartment in the heart of the historic center of Cortona, located on the second floor of an old building, overlooking the beautiful Piazza Signorelli and the theater of the same name. The Casa Teatro is ideal for couples or families with children who want to experience the city, with its enchanting views, typical cuisine and visit the prestigious MAEC museum. Great as a starting point for visiting Montepulciano, Arezzo, Assisi, Perugia, Siena, Pienza or reaching Florence and Rome by train.

FamilyLocationView

Guest favorite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

Rural Tuscany | Family farmstay with restaurant

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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Top guest favorite
Home in Cortona
5.0 out of 5 average rating, 25 reviews

Breathtaking views: Historic House w/Terrace & BBQ

Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, quiet, and the atmosphere of an authentic home.

FamilyLocationComfort

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
5.0 out of 5 average rating, 96 reviews

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.

LocationFamilyCleanliness

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
4.99 out of 5 average rating, 222 reviews

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.

LocationFamilyAir conditioning

Top guest favorite
A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.
Apartment in Cortona
4.97 out of 5 average rating, 187 reviews

CasaNella: central, bright, and panoramic

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

LocationValueAmenities

Top guest favorite
A light-filled living room features a cozy, L-shaped couch adorned with decorative cushions. A small round table sits between two green glass vases, while glass doors lead to an outdoor area. The wooden ceiling and neutral tones create a serene ambiance.
Home in Cortona
5.0 out of 5 average rating, 75 reviews

Casa Primo Stylish-townhouse w/ patio & jetted tub

Casa Primo is located in the heart of the historic center of Cortona. The property is ideally located for travelers who want to savor and be carried away by the colors and flavors of Cortona, a small Etruscan wonder, with its alleys, views, artisan shops, restaurants and art. Casa Primo, with its secret garden, will welcome you in a magical atmosphere in perfect balance between past and future, creating a unique space.

LocationFamilyCheck-in

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
4.94 out of 5 average rating, 224 reviews

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!

ValueFamilyWifi

Top guest favorite
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Apartment in Cortona
4.96 out of 5 average rating, 419 reviews

Cortona Shabby Chic House - independent & balcony-

This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation

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Popular amenities for Cortona vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Cortona's top sights

Museo dell'Accademia Etrusca

84 locals recommend

Girifalco Fortress

66 locals recommend

Basilica Of Saint Margaret Of Cortona

36 locals recommend

Boutique hotels in Cortona

Top guest favorite
The exterior of a historic brick building is illuminated at dusk, highlighting architectural details such as arched windows and a staircase. Lush greenery and lavender plants enhance the landscaped garden, while soft lighting creates a welcoming ambiance throughout the property.
Hotel room in Bettolle
4.94 out of 5 average rating, 280 reviews

Nice double room in a charming B&B

FamilyValueBathroom

Guest favorite
Hotel room in Pogi
4.94 out of 5 average rating, 109 reviews

Borgo Iesolana Country Retreat Suite with terrace

LocationFamilyComfort

Top guest favorite
A spacious bedroom features a large bed with light bedding. Exposed stone walls and wooden beams contribute to the rustic charm. A stylish bathtub and modern vanity are visible, while natural light illuminates the room from windows nearby.
Hotel room in Passignano sul Trasimeno
5.0 out of 5 average rating, 86 reviews

Boutique room - Tower - From Hill to Hill

ValueLocationHospitality

Top guest favorite
Aerial view of a renovated Tuscan farmhouse is presented, surrounded by lush vineyards and rolling fields. A rectangular infinity pool is visible amidst the green landscape, highlighting the tranquil setting. Traditional stone buildings with rustic roofs blend harmoniously with the natural surroundings.
Hotel room in Montepulciano
4.97 out of 5 average rating, 38 reviews

Agriturismo Merigge Wellness & Spa Montepulciano

LocationValueComfort

Superhost
A stone building with a rustic aesthetic is framed by lush greenery and blooming pink roses. The garden features a pergola, surrounded by various plants, creating a serene and inviting outdoor space. A clear sky with soft clouds enhances the tranquil atmosphere.
Hotel room in Piegaro

Room in Historical Residence, Abbey, farmhouse

A cozy double bedroom features a spacious bed with simple bedding. Light floods through open green shutters, illuminating the rustic wooden beams above. A small wooden chair is positioned near a simple table, while an ensuite area with a sink is visible to the side.
Hotel room in Torrita di Siena
5.0 out of 5 average rating, 5 reviews

Follonico - Standard Room Montefollonico

LocationGetting aroundHot tub

Hotel room in Civitella in Val di Chiana
4.91 out of 5 average rating, 23 reviews

Romantic Living!

ValueLocationKitchen

Hotel room in Chiusi
4.8 out of 5 average rating, 5 reviews

Mustiola - Deluxe Suite with outdoor patio

FamilyLocationCondition

Other great vacation rentals in Cortona

Guest favorite
The image captures a quiet evening view of a historic town, with softly lit buildings nestled among lush greenery. A faint outline of a church is visible against the darkening sky, while the surrounding hills add a sense of depth to the scene.
Apartment in Cortona
4.92 out of 5 average rating, 25 reviews

Bel Tramonto, historic center with private garden

FamilyLocationWalkability

Guest favorite
The lounge room features a charming design with pale pink walls and a richly decorated ceiling. An ornate chandelier hangs above, illuminating an antique wooden cabinet and a comfortable seating arrangement with light-colored sofas. A round, decorative coffee table sits at the center, adding functionality.
Apartment in Cortona
4.9 out of 5 average rating, 62 reviews

Casa Nobile

LocationFamilyDecor

Guest favorite
Apartment in Cortona
4.79 out of 5 average rating, 24 reviews

Appartamento La Corte

LocationFamilyCondition

Top guest favorite
Apartment in Cortona
5.0 out of 5 average rating, 45 reviews

Casa AlMa: air conditioning and private terrace

LocationAmenitiesCondition

Top guest favorite
Farm stay in Cortona
5.0 out of 5 average rating, 35 reviews

Relaxing-unspoiled country place Il Monte...

LocationFamilyBreakfast

Top guest favorite
A sunlit terrace is furnished with a dining table surrounded by four chairs, set with plates and fresh fruit. Bougainvillea blooms and a trellis with greenery adorn one wall, while a shaded area is provided by an awning overhead.
Apartment in Cortona
4.98 out of 5 average rating, 88 reviews

Terrazza Silena, historic center with Cortona view!

FamilyLocationCleanliness

Top guest favorite
Apartment in Cortona
5.0 out of 5 average rating, 49 reviews

Ca' delle Acquarelli

FamilyLocationWalkability

Top guest favorite
The living area features exposed stone walls and wooden beams, creating a rustic ambiance. A spacious sectional sofa is complemented by a round accent chair. A round mirror reflects light from the window, while a decorative fireplace adds warmth to the space.
Home in Castiglion Fiorentino
5.0 out of 5 average rating, 53 reviews

Hidden gem in Tuscany

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Frequently Asked Questions

  • What are the best places to stay in Cortona?

    Cortona has stays in the historic center, offering proximity to restaurants, main squares, and cultural sites, while rural homes around the town provide peaceful surroundings and countryside views. Both areas are frequently suggested.

  • What are the best things to do in Cortona with kids?

    Visit the Etruscan Museum for interactive exhibits, explore the public gardens, and join family friendly cooking classes or outdoor activities. Many families enjoy sampling gelato in the town square.

  • What are some of the best things to do in Cortona?

    Wander Cortona's hillside streets, explore the historic center, and visit museums highlighting Etruscan history. Many guests enjoy local art galleries, vibrant cafes, and panoramic viewpoints overlooking the valley.

  • How is the weather in Cortona?

    Cortona experiences cool winters around 33–50°F (0–10°C) with occasional rain, and warm, dry summers between 60–89°F (15–32°C). Spring and autumn have moderate temperatures with increased rainfall.

  • When is the best time to visit Cortona?

    Late spring and early fall are often recommended for visiting Cortona, with mild temperatures around 66–78°F (19–26°C) and blooming landscapes. These seasons tend to feature cultural events and local festivals.

  • What are the best places to visit in Cortona?

    The MAEC Museum, Piazza della Repubblica, and the Church of Santa Margherita are frequently suggested; these sites showcase Cortona's historic depth and cultural heritage. Scenic overlooks around town offer striking valley views.

  • What are some hiking trails in Cortona?

    Cortona has hillside trails that pass through olive groves, pine woods, and scenic lookout spots near its ancient city walls. Walking paths around the town are often suggested for glimpses of valley views and historic architecture.

  • What are some family activities we can do in Cortona?

    Families can explore public parks, join guided walking tours, and try hands-on crafts or cooking experiences inspired by local traditions. Seasonal outdoor concerts and cultural celebrations are frequently enjoyed together.

  • What are some of the best day trip ideas from Cortona?

    Explore neighboring Tuscan towns known for medieval architecture, wineries, and artisan shops, or visit local countryside estates. Lake Trasimeno and the surrounding villages are frequently suggested for day outings.

  • Are there any pet friendly accommodations available in Cortona?

    Many stays in and around Cortona welcome pets, making it easy to explore the historic streets and nearby parks with your animal companion. Be sure to check each listing's pet policy before booking.

  • What are some local tips for visiting Cortona?

    Start early to enjoy quieter streets and markets, and chat with local artisans for insight into traditional crafts. Light layers are helpful in changing weather, and many spots accept cash or cards.

  • What is Cortona known for?

    Cortona is known for its Etruscan history, medieval architecture, and local Tuscan cuisine. The town’s scenic setting and cultural traditions often attract guests looking to experience authentic Italian life.

  • What are the best hidden gems to explore in Cortona?

    Discover tucked-away alleys with artisan workshops, frescoed chapels, and small local eateries serving traditional dishes. Around Cortona, ancient city walls and quiet green spaces feel less frequented but rewarding.

  • What are the best foods to try in Cortona?

    Try local specialties like wild boar stew, handmade pici pasta, and aged pecorino cheese, often served at traditional trattorias. Seasonal produce, olive oil, and regional wines are frequently highlighted in meals.

  • What should I bring for a trip to Cortona?

    Comfortable walking shoes are useful for hilly cobbled streets, and a light jacket helps during cooler evenings. Bringing a reusable water bottle and sun protection is often suggested, especially in summer.

  • What is the nightlife in Cortona like?

    Cortona’s nightlife leans toward intimate wine bars, outdoor cafes, and occasional live music in local venues. The atmosphere is relaxed, with options for enjoying regional wines or small plates.

  • What are the most popular events or festivals in Cortona?

    Cortona has art and music festivals in the summer, food fairs celebrating Tuscan harvest traditions in autumn, and Holy Week processions that gather locals and visitors in the historic center. These events are frequently suggested ways to experience regional culture.

  • Are there family friendly vacation rentals in Cortona?

    Cortona has a selection of family friendly vacation rentals, many with spacious layouts and access to gardens or kitchens. Families can find homes near the historic center or in quieter areas around town.

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