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

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Check availability on Cortona Hotels with a Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Cortona hotels with a pool

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 spacious room with a large window, a view of a landscape painting, and a desk with a vase of flowers.
A balcony with a pool view, a small table, and a chair.

1. 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.
$247 nightly
$280 total
Oct 25 - Oct 26
Total with taxes and fees
Monastero di Cortona Hotel & Spa
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.
An outdoor dining area with tables set for a meal, surrounded by greenery and trees.
A large estate with a swimming pool, surrounded by lush greenery and hills.

2. Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
  • Tuscan escape with poolside lounging beneath cypress trees and vineyard views.
$627 nightly
$699 total
Oct 9 - Oct 10
Total with taxes and fees
Villa di Piazzano - Small Luxury Hotel of the World
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 balcony with a table and chairs, a potted plant, and a view of a green landscape.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.

3. 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.
$393 nightly
$436 total
Nov 1 - Nov 2
Total with taxes and fees
Il Falconiere - Relais e Chateaux
An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.
A spacious dining area with high ceilings and ornate ceiling decorations, featuring multiple tables set for dining.
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A cozy lounge area with a green sofa, a wooden coffee table, wicker chairs, and a view of a lush landscape through an arched doorway.

4. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
  • Soak up the sun at this luxury retreat featuring both indoor and seasonal outdoor pools.
$527 nightly
$586 total
Oct 7 - Oct 8
Total with taxes and fees
Precise Tale Poggio Alla Sala
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 multiple windows and a courtyard.
A stone building with a tiled roof, a small window, and a metal fence.

5. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
  • Immerse in a seasonal poolside paradise with loungers, umbrellas, and fitness amenities.
$112 nightly
$132 total
Oct 13 - Oct 14
Total with taxes and fees
Villa Borgo San Pietro
A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.
A rustic outdoor dining area with stone walls, a table, and wicker chairs.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

6. 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.
$136 nightly
$159 total
Oct 7 - Oct 8
Total with taxes and fees
Relais Villa Baldelli
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 bedside table with a vase of flowers, a book, and a drawer.

7. Locanda agli Amici

Locanda agli Amici
Cortona
  • Discover seasonal poolside bliss with rooftop views, sun loungers, and umbrellas at this upscale family-friendly retreat.
$99 nightly
$118 total
Oct 25 - Oct 26
Total with taxes and fees
Locanda agli Amici
A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.
A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.
A spacious bathroom with a large wooden bathtub, a freestanding mirror, and a glass-enclosed shower.
A long banquet table with gold candelabras, white flowers, and gold tableware.

8. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
  • Luxurious Tuscan retreat offers poolside bliss with mountain views and spa treatments.
$351 nightly
$396 total
Oct 27 - Oct 28
Total with taxes and fees
Relais La Corte dei Papi
A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.
A bathroom with a stone wall, a large bathtub, and a glass-enclosed shower area.
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.
A bedroom with a bed, a chair, a table with a candle, and a wardrobe.

9. Cortona Resort Spa

Cortona Resort Spa
Cortona
  • Serene seasonal outdoor pool awaits at this rural Italian resort, where massages and hiking trails beckon.
$148 nightly
$166 total
Oct 12 - Oct 13
Total with taxes and fees
Cortona Resort Spa
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.

10. 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.
$78 nightly
$94 total
Oct 27 - Oct 28
Total with taxes and fees
Locanda del Molino
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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 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 a tiled roof, a small window, and a metal fence.
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
$112 nightly
$132 total
Oct 13 - Oct 14
Total with taxes and fees
Villa Borgo San Pietro
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 bedside table with a vase of flowers, a book, and a drawer.

Locanda agli Amici

Locanda agli Amici
Cortona
$99 nightly
$118 total
Oct 25 - Oct 26
Total with taxes and fees
Locanda agli Amici
A rustic outdoor dining area with stone walls, a table, and wicker chairs.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

Relais Villa Baldelli

Relais Villa Baldelli
Cortona
$136 nightly
$159 total
Oct 7 - Oct 8
Total with taxes and fees
Relais Villa Baldelli
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 narrow hallway with a stone wall and a clock.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
$247 nightly
$280 total
Oct 25 - Oct 26
Total with taxes and fees
Monastero di Cortona Hotel & Spa
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.
A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.

Locanda del Molino

Locanda del Molino
Cortona
$78 nightly
$94 total
Oct 27 - Oct 28
Total with taxes and fees
Locanda del Molino
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
$151 nightly
$172 total
Oct 14 - Oct 15
Total with taxes and fees
Cortona Resort - Le Terre Dei Cavalieri
Two people seated at a round table outdoors, with a candle and food on the table, and a large tree in the background.
A bedroom with a bed, a chair, a table with a candle, and a wardrobe.
A spacious hallway with wooden flooring, a wooden cabinet with a mirror, and two candle lanterns.
A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.

Cortona Resort Spa

Cortona Resort Spa
Cortona
$148 nightly
$166 total
Oct 12 - Oct 13
Total with taxes and fees
Cortona Resort 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 spacious, well-lit restaurant with large windows, wooden tables, and potted plants.
A person in a swimming pool with a view of trees and mountains through a window.

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
$393 nightly
$436 total
Nov 1 - Nov 2
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 sauna, a glass-enclosed shower, and a bathtub with a modern design.
A traditional villa with a garden, outdoor seating, and a clear blue sky.
A well-maintained lawn with a brick house and a flag, surrounded by trees and a clear sky.

Casa Bellavista

Casa Bellavista
Cortona
$182 nightly
$205 total
Oct 18 - Oct 19
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 historic stone building with arched doorways and a courtyard at twilight.
A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.
A long banquet table with gold candelabras, white flowers, and gold tableware.

Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
$351 nightly
$396 total
Oct 27 - Oct 28
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.
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Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"There is nothing to fault here, it’s a perfect hotel. Staff are brilliant, and the buildings and grounds are really well looked after. Breakfast and lunch are ideal too."
James 4-night trip
Posted 1 day ago
Il Falconiere - Relais e Chateaux
Villa Borgo San Pietro

Villa Borgo San Pietro

10/10 Excellent
"Well done"
PIETRO 7-night trip
Posted 3 days ago
Villa Borgo San Pietro
Relais Villa Baldelli

Relais Villa Baldelli

10/10 Excellent
"Such a stunning Tuscany setting"
ralph 2-night trip
Posted 5 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
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-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 10 months ago
Relais La Corte dei Papi

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 $86 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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