Find Hotels with a Pool in Chianti Region

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Top Chianti Region Hotels with a Pool

Villa Cassia di Baccano

Loro Ciuffenna
  • Poolside bar
  • Pool loungers
  • Full-service spa
9.4 out of 10, Exceptional, (23)
Poolside bliss defines summer days at this countryside retreat, where seasonal swimming delights both adults and children. Villa Cassia di Baccano elevates the experience with massage services and a convenient bar serving refreshing drinks under the Italian sun.
$133 nightly
The price is $147
Dec 18 - Dec 19
Total with taxes and fees
Villa Cassia di Baccano

Castello di Meleto

Gaiole in Chianti
  • Pool loungers
8.8 out of 10, Excellent, (87)
Vibrant farm stay surrounds a seasonal outdoor pool with sun loungers set amid Tuscan vineyards. Guests can book winery tours, enjoy al fresco dining at La Fornace di Meleto, or explore nearby hiking trails before returning to air-conditioned comfort.
$123 nightly
The price is $145
Nov 27 - Nov 28
Total with taxes and fees
Castello di Meleto

Casa di Palaia

Greve in Chianti
  • Pool
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Housekeeping
10.0 out of 10, Exceptional, (22)
Seasonal swimming delights await at this lakeside guesthouse where private in-room pools complement the outdoor swimming area. Casa di Palaia's restaurant serves meals best enjoyed on the rooftop terrace before exploring nearby hiking trails.
$86 nightly
The price is $99
Dec 15 - Dec 16
Total with taxes and fees
Casa di Palaia

Villa il Fedino

San Casciano in Val di Pesa
  • Pool loungers
9.6 out of 10, Exceptional, (97)
Seasonal outdoor pool creates the perfect summer sanctuary amid the Tuscan countryside. Villa il Fedino delights with spa treatments, Italian cuisine at the on-site restaurant, and complimentary continental breakfast served in al fresco splendor.
$153 nightly
The price is $173
Dec 19 - Dec 20
Total with taxes and fees
Villa il Fedino

Castello di Tornano Wine Resort

Gaiole in Chianti
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (100)
Seasonal swimming awaits at this Tuscan farm stay, where sun loungers border the refreshing outdoor pool. Beyond aquatic relaxation, guests discover an attached winery, tennis court, and complimentary breakfast buffet amid Castle of Brolio's enchanting landscape.
$183 nightly
The price is $211
Nov 29 - Nov 30
Total with taxes and fees
Castello di Tornano Wine Resort

Resort 37

4.0 star property
Rignano sull'Arno
  • Pool loungers
9.8 out of 10, Exceptional, (36)
$217 nightly
The price is $241
Dec 19 - Dec 20
Total with taxes and fees
Resort 37

Casale La Gora

Figline e Incisa Valdarno
  • Pool loungers
9.6 out of 10, Exceptional, (21)
Swimming season stretches from May to October at this countryside retreat's outdoor pool, complete with loungers and umbrellas. Beyond refreshing dips, travelers find bicycle rentals, hiking trails, and a firepit for evening relaxation.
$89 nightly
The price is $101
Dec 19 - Dec 20
Total with taxes and fees
Casale La Gora

Hotel Borgo di Cortefreda Relais

4.0 star property
Barberino Tavarnelle
  • Poolside bar
  • Pool loungers
  • Full-service spa
9.4 out of 10, Exceptional, (476)
Sparkling waters await at the seasonal outdoor pool, complete with comfortable loungers and refreshing poolside bar service. Beyond aquatic pleasures, this Tuscan retreat offers spa treatments, hiking trails, and wine tasting experiences amid stunning countryside views.
$64 nightly
The price is $77
Nov 30 - Dec 1
Total with taxes and fees
Hotel Borgo di Cortefreda Relais

Villa Sabolini

4.0 star property
Colle di Val d'Elsa
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.2 out of 10, Wonderful, (188)
Sparkling waters beckon amid the Italian countryside at this hotel's inviting outdoor pool. Guests relax on stylish loungers while sipping refreshing drinks from the poolside bar after cycling adventures on nearby hiking trails.
$92 nightly
The price is $105
Nov 30 - Dec 1
Total with taxes and fees
Villa Sabolini

Hotel Colle Etrusco Salivolpi

3.0 star property
Castellina in Chianti
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (111)
Poolside bliss beckons at this Tuscan hotel where the seasonal outdoor pool offers respite from May through September. Comfortable loungers, shady umbrellas, and a convenient poolside bar complement hiking trails and mountain biking adventures nearby.
$99 nightly
The price is $113
Dec 2 - Dec 3
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
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