7 best hotels with a pool in Cortona
Search hotels in Cortona →
Why hotels with a pool, why here
Hotels with a pool in Cortona suit travellers who want that rare Tuscan combination of old-town ambience and genuine relaxation. Cortona sits high above the Val di Chiana, so many pool properties offer big-sky views over the countryside and late-summer sunsets—perfect for unwinding after exploring the historic centre around Piazza della Repubblica, Cortona’s civic hub. For day-to-day sightseeing, the medieval core rewards slow strolling between landmarks such as the Palazzo Comunale in the same square and viewpoints reached from the hilltop areas.
A hotel is a *true* “Hotels with a pool” pick in Cortona when the pool is usable (size, privacy, and seasonal comfort), well-integrated into the property (terraces, sun loungers, shade), and supported by service—rather than being an afterthought. Look for properties that feel like a base: tranquil grounds for reading and swimming, yet still practical for getting back to Cortona’s centre for dinner.
In particular, pool hotels tend to suit couples, honeymooners, and groups seeking a countryside rhythm with downtime built in. For stylish, full-service stays, examples from our bookable inventory include Monastero di Cortona Hotel & Spa (5★) and Cortona Resort & Spa (4★). For those preferring a calmer, more intimate feel, Villa Il Trebbio and Villa Augusto are standout choices, while Hotel Villa Marsili (4★) offers an elegant balance of comfort and access.
The list
A selection of hotels to compare for your stay.
- 01★★★★
Relais Villa Baldelli
Relaxed Tuscan country stay near Cortona with a spacious, uncrowded pool area.
- 03★★★★
Cortona Resort & Spa
Relaxed Tuscan resort outside Cortona with a heated spa pool that draws focus.
- 04
Villa Augusto
A Tuscan hill villa near Cortona, with a pool area guests call exquisite.
- 05
- 06★★★
Monastero San Silvestro
Countryside monastery apartments near Cortona, with a clean outdoor pool and buffet breakfast.
- 07★★★★
Locanda agli Amici
Relaxed Tuscan hideaway in Cortona’s church zone with a pool terrace facing Lake Trasimeno.
- 08★★★
Agriturismo Cortoreggio
Relaxed farm stay near Cortona with lakeview gardens, two pools, and space for families.
Where the picks sit
What to know about hotels with a pool in Cortona
What makes a hotel a good “Hotels with a pool” option in Cortona?
Prioritise a properly set-up pool area (space, loungers, privacy and comfort) plus facilities that make relaxing easy after sightseeing.
Which area of Cortona is best to stay in?
Most guests base themselves close enough for easy access to the historic centre around Piazza della Repubblica, or choose hillside properties slightly outside town for views and a quieter atmosphere.
What price levels can I expect, roughly?
Options range from budget-focused 1★ stays to mid-range and luxury 4★/5★ hotels, with pool comfort and service typically increasing with star rating.