The Best Hotels with a Pool in Chianti Region from SAR 389 in 2026

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region hotels with a pool

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.

SAR 1,239

SAR 1,405 total

includes taxes & fees

30 Oct - 31 Oct

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

A restaurant with a table set for two, overlooking a scenic landscape.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

An outdoor dining area with a pool, potted plants, and umbrellas.

2. Relais Vignale & Spa

Radda in Chianti

Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.

SAR 610

SAR 800 total

includes taxes & fees

16 Oct - 17 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.

A room with a view of a forest through a window, a table with a lamp, and a chair.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

3. Dievole Wine Resort

Castelnuovo Berardenga

Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.

SAR 940

SAR 1,068 total

includes taxes & fees

9 Nov - 10 Nov

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

4. Hotel Villa Campomaggio

Radda in Chianti

Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.

SAR 619

SAR 707 total

includes taxes & fees

3 Nov - 4 Nov

A person sitting by a swimming pool with a stone building in the background.

A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

A stone building with a wooden door and an arched window.

A bartender at a bar with a variety of liquor bottles in the background.

5. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Discover a Tuscan oasis with a seasonal pool sanctuary, loungers for sunbathing, and poolside drinks service in wine country.

SAR 434

SAR 503 total

includes taxes & fees

14 Nov - 15 Nov

A clear swimming pool with a view of a lush green landscape and distant hills.

A room with a wooden ceiling, a sofa, a coffee table, a lamp, and a TV.

A garden with pink roses, a lawn, and a white umbrella.

A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

6. Villa Le Barone

Greve in Chianti

Dive into luxury at this Tuscan retreat with 2 outdoor pools, mountain views, and a poolside bar for ultimate relaxation.

SAR 1,036

SAR 1,165 total

includes taxes & fees

31 Oct - 1 Nov

An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

7. Borgo Vescine

Radda in Chianti

Slip into Tuscan bliss at this pool paradise with vineyard views and poolside bar service.

SAR 1,562

SAR 1,752 total

includes taxes & fees

4 Nov - 5 Nov

A pool with a view of a lush valley and distant buildings.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.

8. Castello Vicchiomaggio

Greve in Chianti

Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.

SAR 683

SAR 752 total

includes taxes & fees

29 Oct - 30 Oct

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Choose what matters most at hotels with a pool in Chianti Region

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Chianti Region

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

A dining area with a table set for two, featuring wine bottles and bread.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

Castello La Leccia

Castellina in Chianti

SAR 750

SAR 842 total

includes taxes & fees

2 Nov - 3 Nov

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone archway leading to a window with a view of tall trees and a distant landscape.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A stone building with a tower, surrounded by people dining at tables with candles.

Castello di Tornano Wine Resort

Gaiole in Chianti

SAR 571

SAR 661 total

includes taxes & fees

25 Oct - 26 Oct

Castello Vicchiomaggio

Greve in Chianti

SAR 683

SAR 752 total

includes taxes & fees

29 Oct - 30 Oct

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A poolside area with lounge chairs and a view of the night sky.

A person relaxing in a hot tub with a view of a building and trees in the background.

Belvedere di San Leonino

Castellina in Chianti

SAR 406

SAR 472 total

includes taxes & fees

16 Oct - 17 Oct

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

A historic building with a stone facade, arched entrance, and a wooden balcony.

A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

SAR 404

SAR 453 total

includes taxes & fees

8 Nov - 9 Nov

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A stone building with a courtyard, a covered seating area, and a small bell tower.

A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

A cozy living room with a stone fireplace, striped sofas, and a coffee table.

Borgo di Pietrafitta Relais

Castellina in Chianti

SAR 331

SAR 381 total

includes taxes & fees

1 Nov - 2 Nov

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

SAR 330

SAR 389 total

includes taxes & fees

13 Nov - 14 Nov

A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.

A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

A bedroom with a large bed, a bedside table, and a chair.

Borgo Del Cabreo

Greve in Chianti

SAR 784

SAR 880 total

includes taxes & fees

18 Oct - 19 Oct

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

SAR 434

SAR 503 total

includes taxes & fees

14 Nov - 15 Nov

A couple dining at an outdoor table with a view of the countryside.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

A narrow street with buildings on either side, a flag, and a bench.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

SAR 437

SAR 506 total

includes taxes & fees

2 Nov - 3 Nov

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