Hotels with a Pool in Montemassi

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Sep 22 - Sep 23

Tomorrow

Sep 23 - Sep 24

This weekend

Sep 25 - Sep 27

Next weekend

Hotels with a Pool in Montemassi

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Montemassi on Hotels.com. These Montemassi Hotels with a Pool consistently deliver on quality, location and traveler experience. Last updated on September 22, 2026.

A historic stone building with multiple windows and a courtyard.

A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.

An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

A bathroom with a large sink, mirror, shower, toilet, and a towel rack.

1. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Outdoor pool
Pool loungers

CNY684

CNY768 total

includes taxes & fees

Sep 27 - Sep 28

A poolside area with a wooden deck, lounge chairs, and a stone building with arched windows.

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

A cozy living room with a fireplace, wooden beams, stone walls, and a leather sofa.

A wooden interior with a table set for a meal, featuring a tray with plates, glasses, and a bottle.

2. Conti di San Bonifacio Wine Resort

Gavorrano

Outdoor pool
Poolside bar
Pool loungers

CNY4,135

CNY4,579 total

includes taxes & fees

Oct 15 - Oct 16

A swimming pool with a view of a valley and mountains.

A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.

An outdoor dining area with tables set for a meal, surrounded by greenery and a wooden pergola.

A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

3. Valdonica Winery & Vineyard Residence

Roccastrada

Full-service spa

CNY981

CNY1,102 total

includes taxes & fees

Oct 11 - Oct 12

A swimming pool with clear blue water, a person standing on the edge, and another person swimming. There are lounge chairs and an umbrella in the background.

A hotel room with a fireplace, a desk with a chair, a bed with a blue and white bedspread, and a view of the outdoors through large windows.

A Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.

A balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.

4. Tenuta il Sassone - Wine & Food

Gavorrano

Pool loungers

CNY773

CNY904 total

includes taxes & fees

Oct 6 - Oct 7

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

A large, multi-story building surrounded by lush greenery and fields.

An indoor water feature with a brick archway and a view to the outside.

A spacious lounge area with a high ceiling, ornate chandelier, and a variety of seating options including sofas and armchairs.

5. L'Andana

Castiglione della Pescaia

2 outdoor pools
Indoor pool
Pool loungers
Hot tub

CNY2,899

CNY3,266 total

includes taxes & fees

Oct 4 - Oct 5

A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.

A cozy living room with a fireplace, elegant furniture, and a chandelier.

A bathroom with a bathtub, a chandelier, and a view of the outdoors.

A rustic dining area with brick walls, hanging plants, and candle-lit tables.

6. Borgo Santo Pietro

Chiusdino

Outdoor pool
Poolside bar
Pool loungers
Hot tub

CNY7,675

CNY8,519 total

includes taxes & fees

Sep 30 - Oct 1

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

A large stone house with a swimming pool, surrounded by lush greenery and hills.

A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.

7. La Melosa Resort & Spa - Adults Only

Roccastrada

Outdoor pool
Poolside bar
Pool loungers
Hot tub

CNY657

CNY746 total

includes taxes & fees

Oct 15 - Oct 16

A marina with multiple boats, lounge chairs, and umbrellas.

A balcony with a view of a marina filled with boats, a table with a hat, and a towel.

A poolside area with lounge chairs and umbrellas, a wooden deck, and a backdrop of sailboats.

A person doing yoga on a balcony with a marina and boats in the background.

8. Marina di Scarlino Resort

Scarlino

Poolside bar
Pool loungers
Hot tub

CNY1,940

CNY2,134 total

includes taxes & fees

Oct 12 - Oct 13

A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

A bedroom with a large bed, a desk, and a view of the outdoors.

A table set with a charcuterie board, wine glasses, and a basket of bread.

A kitchen with a stone archway, a dining table with chairs, and a view of the outside through a glass door.

9. Fattoria Maremmana

Grosseto

2 outdoor pools
Poolside bar
Pool loungers

CNY1,473

CNY1,650 total

includes taxes & fees

Sep 27 - Sep 28

A group of people dining at a table with a view of a valley and mountains.

A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.

A long table set for a formal outdoor event, surrounded by a vineyard.

A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

10. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Restaurant

CNY1,270

CNY1,412 total

includes taxes & fees

Oct 4 - Oct 5

A pool with a modern water feature and a stone structure.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

A buffet table with various desserts and a long dining area with tables and chairs.

11. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Indoor pool
Poolside bar
Hot tub

CNY576

CNY633 total

includes taxes & fees

Sep 28 - Sep 29

12. Riva del Sole Resort & SPA

Castiglione della Pescaia

2 outdoor pools
Indoor pool
Pool loungers
On private beach

CNY1,652

CNY1,854 total

includes taxes & fees

Oct 10 - Oct 11

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

A spacious living room with a fireplace, multiple seating options, and large windows with curtains.

A historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.

A rustic stone building with a tiled roof, a covered patio with outdoor seating, and well-maintained gardens.

13. Antico Casale L'Impostino

Civitella Paganico

Pool loungers

CNY895

CNY984 total

includes taxes & fees

Oct 19 - Oct 20

A swimming pool with a waterfall feature, large windows, and a lounge chair.

A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.

An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

A covered patio with a table and chairs, a small garden, and a building in the background.

14. Montebelli Agriturismo & Country Hotel

Gavorrano

Outdoor pool
Indoor pool
Pool loungers
Hot tub

CNY662

CNY774 total

includes taxes & fees

Oct 1 - Oct 2

A pool area with lounge chairs and umbrellas, surrounded by buildings and trees.

A golf course with a pond, trees, and hills in the background.

A covered outdoor dining area with tables set for a meal, surrounded by glass walls and wooden beams.

An outdoor dining area with tables set for two, surrounded by palm trees and flowering plants.

15. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Outdoor pool
Poolside bar
Pool loungers
Near private beach

CNY1,183

CNY1,348 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with water flowing from a tap, surrounded by lounge chairs and umbrellas.

A rustic interior with exposed wooden beams, a stone fireplace, a cozy seating area, and a large window with curtains.

A rustic room with a stone wall, a glass table with books, and a view of an outdoor patio with chairs and umbrellas.

An outdoor dining setup with a stone building in the background, a table with plates, cutlery, and a bottle of red drink.

16. Tenuta Casteani

Gavorrano

2 outdoor pools
Poolside bar
Pool loungers
Hot tub

CNY898

CNY1,018 total

includes taxes & fees

Sep 27 - Sep 28

A person in a hot tub with water flowing over them.

A room with a sofa, a coffee machine, and a decorative plant.

A sauna with benches and a glass partition.

A hotel named GRANDVCA with a fountain in the center, surrounded by a paved area with potted plants.

17. Granduca

Grosseto

Indoor pool
Hot tub

CNY689

CNY792 total

includes taxes & fees

Sep 27 - Sep 28

A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.

A window with a view of buildings and a plant on the windowsill.

A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

18. Country House il Ciliegio

Roccastrada

Poolside bar
Pool loungers

CNY587

CNY661 total

includes taxes & fees

Oct 23 - Oct 24

A clear pool with visible mineral deposits, a pebble beach, and a mountainous landscape in the background.

A rustic interior with exposed brick walls, a stone fireplace, and wooden beams. There are leather sofas, a round table, and potted plants.

A table set outdoors with a view of rolling hills and a tall tree in the background.

An open window with a view of a mountainous landscape and a flower box on the windowsill.

19. VIN Hotel - La Meridiana

Montieri

Pool loungers

CNY980

CNY1,078 total

includes taxes & fees

Sep 28 - Sep 29

A stone building with a swimming pool, lounge chairs, and umbrellas.

An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.

A stone wall with a view of rolling hills and mountains.

A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

20. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

Poolside bar

CNY9,280

CNY10,284 total

includes taxes & fees

Oct 21 - Oct 22

See more properties

Discover your perfect hotel with a pool in Montemassi

Breakfast included

4 stars

5 stars

Hot tub

Spa