A hillside town with historic buildings, a church, and vineyards.

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Check availability on Cortona Hotels with a Pool

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Cortona hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.
A rustic outdoor dining area with stone walls, a table, and wicker chairs.

1. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
  • Dive into cooling bliss at this upscale hotel's seasonal outdoor pool with lounger service and refreshing drinks.
$119 nightly
$140 total
Sep 28 - Sep 29
Total with taxes and fees
Relais Villa Baldelli
A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A stone building with outdoor seating and a fountain.
A stone building with a tiled roof, a small window, and a metal fence.

2. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
  • Immerse in a seasonal poolside paradise with loungers, umbrellas, and fitness amenities.
$111 nightly
$131 total
Sep 27 - Sep 28
Total with taxes and fees
Villa Borgo San Pietro
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A person in a white robe standing by a window with a view of mountains.
A couple dining at a table with a scenic view of mountains and a lake.
A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

3. Locanda agli Amici

Locanda agli Amici
Cortona
  • Discover seasonal poolside bliss with rooftop views, sun loungers, and umbrellas at this upscale family-friendly retreat.
$126 nightly
$148 total
Sep 21 - Sep 22
Total with taxes and fees
Locanda agli Amici
A pool area with lounge chairs, a hot tub, and a view of mountains.
A terrace with sun loungers, stone walls, and potted plants.
A balcony with a pool view, a small table, and a chair.
A spacious room with a large window, a view of a landscape painting, and a desk with a vase of flowers.

4. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
  • Luxurious indoor pool sanctuary awaits at this historic Cortona monastery, where relaxation flows from spa waters to garden views.
$354 nightly
$399 total
Aug 30 - Aug 31
Total with taxes and fees
Monastero di Cortona Hotel & Spa
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A stone building with a rustic exterior, a wooden door, and a sign that reads "MOLINO".

5. Locanda del Molino

Locanda del Molino
Cortona
  • Take a dip in the outdoor pool surrounded by Tuscan scenery while sipping refreshing drinks from the poolside bar.
$94 nightly
$113 total
Sep 28 - Sep 29
Total with taxes and fees
Locanda del Molino
A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.
A spacious hallway with wooden flooring, a wooden cabinet with a mirror, and two candle lanterns.
A bedroom with a bed, a chair, a table with a candle, and a wardrobe.
A round table set for dining with candles, wine glasses, and a bottle of wine. A stone wall and wooden furniture are in the background.

6. Cortona Resort Spa

Cortona Resort Spa
Cortona
  • Serene seasonal outdoor pool awaits at this rural Italian resort, where massages and hiking trails beckon.
$141 nightly
$158 total
Sep 1 - Sep 2
Total with taxes and fees
Cortona Resort Spa
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.
A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

7. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
  • Elegant farmhouse pool retreat immerses guests in the Tuscan countryside with dining steps away.
$137 nightly
$156 total
Sep 23 - Sep 24
Total with taxes and fees
Cortona Resort - Le Terre Dei Cavalieri
A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.
A historic stone building with arched doorways and a courtyard at twilight.
A spacious bathroom with a large wooden bathtub, a freestanding mirror, and a glass-enclosed shower.
A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.

8. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
  • Luxurious Tuscan retreat offers poolside bliss with mountain views and spa treatments.
$387 nightly
$435 total
Sep 17 - Sep 18
Total with taxes and fees
Relais La Corte dei Papi
A person in a swimming pool with a view of trees and mountains through a window.
A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.
A spacious, well-lit restaurant with large windows, wooden tables, and potted plants.

9. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
  • Luxurious Tuscan retreat offers twin outdoor pools, winery access, and poolside dining with stunning vineyard views.
$514 nightly
$575 total
Sep 29 - Sep 30
Total with taxes and fees
Il Falconiere - Relais e Chateaux
A rectangular swimming pool with clear blue water, surrounded by a paved deck and a gazebo.
An outdoor dining table set with tea, coffee, and pastries, surrounded by white metal chairs and a stone fountain in the background.
A formal dining room with a large table, chairs, and a chandelier.
A rustic dining area with a brick fireplace, wooden table, and chairs.

10. Agriturismo Villa Augusto

Agriturismo Villa Augusto
Cortona
  • Seasonal pool paradise with tennis court and free bicycles offers a refreshing Italian farmhouse retreat in the countryside.
$221 nightly
$249 total
Sep 5 - Sep 6
Total with taxes and fees
Agriturismo Villa Augusto
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Choose what matters most at hotels with a pool in Cortona

Breakfast included
5 stars
4 stars
Spa
Hot tub

Hotels with pools and free breakfast in Cortona

A rustic outdoor dining area with stone walls, a table, and wicker chairs.
A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.

Relais Villa Baldelli

Relais Villa Baldelli
Cortona
$119 nightly
$140 total
Sep 28 - Sep 29
Total with taxes and fees
Relais Villa Baldelli
A stone building with outdoor seating and a fountain.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A stone building with multiple windows and a courtyard.
A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.

Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
$111 nightly
$131 total
Sep 27 - Sep 28
Total with taxes and fees
Villa Borgo San Pietro
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A stone building with a rustic exterior, a wooden door, and a sign that reads "MOLINO".
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.

Locanda del Molino

Locanda del Molino
Cortona
$94 nightly
$113 total
Sep 28 - Sep 29
Total with taxes and fees
Locanda del Molino
A person in a white robe standing by a window with a view of mountains.
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A couple dining at a table with a scenic view of mountains and a lake.
A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

Locanda agli Amici

Locanda agli Amici
Cortona
$126 nightly
$148 total
Sep 21 - Sep 22
Total with taxes and fees
Locanda agli Amici
Two people seated at a round table outdoors, with a candle and food on the table, and a large tree in the background.
A two-story building with a stone staircase leading to a door, a scooter parked in front, and a garden with potted plants.
A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.
A spacious hallway with wooden flooring, a wooden cabinet with a mirror, and two candle lanterns.

Cortona Resort Spa

Cortona Resort Spa
Cortona
$141 nightly
$158 total
Sep 1 - Sep 2
Total with taxes and fees
Cortona Resort Spa
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.
A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
$137 nightly
$156 total
Sep 23 - Sep 24
Total with taxes and fees
Cortona Resort - Le Terre Dei Cavalieri
A terrace with sun loungers, stone walls, and potted plants.
A pool area with lounge chairs, a hot tub, and a view of mountains.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.
A narrow hallway with a stone wall and a clock.

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
$354 nightly
$399 total
Aug 30 - Aug 31
Total with taxes and fees
Monastero di Cortona Hotel & Spa
A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.
A person in a swimming pool with a view of trees and mountains through a window.
A person standing at the entrance of a building with a stone staircase leading up to a door.

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
$514 nightly
$575 total
Sep 29 - Sep 30
Total with taxes and fees
Il Falconiere - Relais e Chateaux
A large, rectangular swimming pool surrounded by a well-maintained lawn, with a house and garden in the background.
A traditional villa with a garden, outdoor seating, and a clear blue sky.
A sauna, a glass-enclosed shower, and a bathtub with a modern design.
A well-maintained lawn with a brick house and a flag, surrounded by trees and a clear sky.

Casa Bellavista

Casa Bellavista
Cortona
$209 nightly
$235 total
Sep 29 - Sep 30
Total with taxes and fees
Casa Bellavista
A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.
A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.
A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.
A historic stone building with arched doorways and a courtyard at twilight.

Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
$387 nightly
$435 total
Sep 17 - Sep 18
Total with taxes and fees
Relais La Corte dei Papi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Cortona Hotel Reviews

Relais Villa Baldelli

Relais Villa Baldelli

8/10 Good
"The property was relaxing and quaint. The pool was nice and the overall Tuscan country vibe and decor was nice. The location was good and the rooms were spacious. It was not walkable to anything but if you have a rental car the location is great because Cortana is a wonderful town. The staff is kind and responsive however I had an issue with the cleaning ladies where they disposed of thing of my mine thinking it was trash. I found it odd that cleaning folks would take it upon themselves to touch my things as all. I asked them to not to clean our room anymore and they did it again the next day due to poor internal communication. It was annoying to deal with that but still I would say the staff tried their best to be helpful. Lastly, I was not a fan of their breakfast. They had the basics that were heavily rooted in sweets and pork both of which I don’t eat. They made fresh plain eggs but some veggies and maybe turkey meat would have been nice. Overall, for the price point this place is good."
Shabnam Karimi 4-night trip
Posted 6 days ago
Relais Villa Baldelli
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Yan Bo 1-night trip
Posted 11 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Relais La Corte dei Papi

Relais La Corte dei Papi

10/10 Excellent
"Our visit was like being spoiled from the moment we arrived! The staff and even the owner were there to make sure we had everything we needed! Though our visit was in the off season, the only thing we didn't get to use was the pool as it was just too cold. The breakfast, though, was the best we have ever had while traveling! Highly recommend!!!"
Traci 4-night trip
Posted 9 months ago
Relais La Corte dei Papi
Locanda del Molino

Locanda del Molino

10/10 Excellent
"family run business with great hospitality and excellent food"
stefania 1-night trip
Posted 9 months ago
Locanda del Molino

Frequently asked questions

How much does a hotel with outdoor pool in Cortona cost?
Enjoy staying in a hotel in Cortona with an outdoor pool. You can find a great deal from $113 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Cortona that have private outdoor pools?
In the charming city of Cortona, there are several delightful accommodations featuring private outdoor pools, superb for families seeking a tranquil retreat.One standout option is the Attractive Renovated Stone Mill House, which offers a lovely private pool along with a cozy kitchen, ideal for preparing family meals. Rated 9.0 by travellers, this property can comfortably sleep up to five people and provides a serene patio area, superb for enjoying the stunning Tuscan landscape.Another exceptional choice is the Apartment "Agriturismo Le Bosole" - Val di Pierle, boasting a superb review score of 10.0. This inviting apartment not only features a private pool but also includes a spacious patio and kitchen, ensuring that families have all the conveniences they need for a relaxing stay. Nearby museums add a touch of culture to your visit, making it a fantastic all-around option.For those looking for a more traditional Tuscan experience, the Beautiful Tuscan farmhouse in the countryside with a swimming pool is another top-rated accommodation, also receiving a superb score of 10.0. This property is surrounded by the stunning mountains of Tuscany, offering outdoor enthusiasts nearby biking opportunities, along with a secured private pool that ensures peace of mind for families.
Are there hotels in Cortona with outdoor pool cabanas or loungers?
Il Falconiere - Relais e Chateaux is a stunning 5-star hotel located in the picturesque landscape of Cortona, offering an exquisite outdoor pool experience. Guests rave about the luxurious poolside cabanas, which are complimentary, providing the great spot to unwind under the Tuscan sun. With plush sun loungers available, families can easily relax while enjoying the beautiful views of the surrounding vineyards.In addition to the relaxing pool amenities, Il Falconiere excels in creating memorable experiences with its nearby winery tours and private tastings. Reviewers consistently highlight the exceptional quality of the on-site restaurant, often describing it as "amazing," which adds to the overall allure of this delightful hotel.
Which Cortona hotels offer poolside service for food and drinks?
Villa di Piazzano - Small Luxury Hotel of the World is a stunning 5-star option in Cortona, where you can enjoy exceptional poolside service. Guests rave about the attentive staff and the lovely atmosphere surrounding the outdoor pool, complete with a poolside bar that makes indulging in snacks and refreshing drinks a breeze. With a remarkable traveller rating of 9.8, this hotel is renowned for its beautiful location and spacious suites, offering a luxurious retreat for families and couples alike.Another excellent choice is Cortona Resort - Le Terre Dei Cavalieri, which also features an outdoor pool and a convenient poolside bar. With the same impressive review score of 9.8, this resort provides a welcoming environment for families, offering free breakfast and self-parking options, ensuring a straightforward experience.Il Falconiere - Relais e Chateaux, another five-star gem, boasts an outdoor pool with complimentary cabanas and a poolside bar. Guests appreciate the great pool experience and the amazing on-site restaurant, all contributing to its stellar 9.4 rating.Lastly, Relais La Corte dei Papi and Relais Villa Baldelli, both rated above 9.0, also offer poolside bars, allowing guests to enjoy food and drinks while soaking up the Tuscan sun.
Is it cheaper to book flights and a Cortona hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Cortona for you.

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