An ancient stone tower with a view of rolling hills and fields in the background.

Roccastrada Hotel Guide - Hotels with Pool in Roccastrada, Tuscany

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Roccastrada Hotels with Pool

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Roccastrada hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
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.
A cozy living room with a fireplace, bookshelves, and a dining area.

1. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
  • Poolside paradise creates an oasis of serenity at this resort with mountain views.
€130
includes taxes & fees
31 Aug - 1 Sept
La Melosa Resort & Spa - Adults Only
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.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

2. Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
  • Serene seasonal pool surrounded by Tuscan countryside views awaits at this charming farmstay offering rooftop terrace relaxation.
€100
includes taxes & fees
2 Sept - 3 Sept
Agriturismo Tenuta di Montemassi La Fattoria
A swimming pool with a view of a valley and mountains.
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

3. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
  • Swim in Tuscan splendour at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
€144
includes taxes & fees
27 Sept - 28 Sept
Valdonica Winery & Vineyard Residence
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 room with a wooden bed, a bathroom with a shower, and a purple wall.

4. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
  • Wine country retreat with a seasonal outdoor pool and on-site vineyard makes for a splendid Tuscan escape.
€169
includes taxes & fees
30 Sept - 1 Oct
Valdonica Winery - Chill in Nature Lodge
A serene pool area with lounge chairs and a clear view of the sunset over a hilly landscape.
A cozy tent interior with a cushioned seating area, a small table with a vase, a potted plant, and a bed with patterned bedding.
A hand under a showerhead with water flowing into a basin, overlooking a landscape with trees and hills.
A tent with a bed, a wooden chair, a small table, and a rug.

5. Equipped glamping tent and infinity pool in a Tuscan olive grove

Equipped glamping tent and infinity pool in a Tuscan olive grove
Roccastrada
€154
includes taxes & fees
1 Sept - 2 Sept
Equipped glamping tent and infinity pool in a Tuscan olive grove
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.
A tent with a wooden deck, a table with chairs, and a view of olive trees and hills.
A tent interior with a bed, a fan, a shelf with folded clothes, and a patterned rug.
An olive grove with several white-roofed structures, likely accommodations, amidst the trees.

6. Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
€170
includes taxes & fees
1 Sept - 2 Sept
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.
A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.
A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

7. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
€108
includes taxes & fees
1 Sept - 2 Sept
Country House il Ciliegio
A swimming pool with a view of a hilltop castle.
A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.
A modern bathroom with a glass-enclosed shower, a white sink, and a large mirror.
A courtyard with a stone column, potted plants, and a view of a hilltop castle.

8. Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
  • Wine country farm stay with a seasonal pool perfect for summer dips in the Tuscan sunshine.
€97
includes taxes & fees
14 Sept - 15 Sept
Agriturismo Podere Ristella - Wine&Food
A pool surrounded by lush greenery, a stone wall, and a lamp post.
A living room with a fireplace, a television, a dining table with a fruit centerpiece, and a painting on the wall.
A house with a stone wall, a large tree, and a patio with a table and chairs.
A gravel path, tall cypress trees, and a brick wall.

9. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
€5,633
includes taxes & fees
30 Sept - 1 Oct
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.
A person enjoying a water feature with a view of a lush landscape.
A white tent in a grassy field with trees and a mountain in the background.
A tent with a bed, a small stool, and a table with a glass.

10. Stargazer – Your Sky‑View Hideaway in the Tuscan Hills

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
View all properties

Choose what matters most at hotels with a pool in Roccastrada

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Roccastrada

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
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.
A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
€130
includes taxes & fees
31 Aug - 1 Sept
La Melosa Resort & Spa - Adults Only
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
A swimming pool with a view of a valley and mountains.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.
A balcony with two wooden chairs overlooking a vineyard and distant mountains.

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
€144
includes taxes & fees
27 Sept - 28 Sept
Valdonica Winery & Vineyard Residence
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.
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 hotel with a swimming pool, surrounded by greenery and adjacent to a road.

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
€108
includes taxes & fees
1 Sept - 2 Sept
Country House il Ciliegio
A historic stone building with multiple windows and a courtyard.
A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
€100
includes taxes & fees
2 Sept - 3 Sept
Agriturismo Tenuta di Montemassi La Fattoria
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 panoramic view of a vineyard with rolling hills, a clear sky, and distant mountains.

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
€169
includes taxes & fees
30 Sept - 1 Oct
Valdonica Winery - Chill in Nature Lodge
A swimming pool with a view of a hilltop castle.
A wine cellar with wooden barrels, a wine rack, and a table set for dining.
A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.
A courtyard with a stone column, potted plants, and a view of a hilltop castle.

Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
€97
includes taxes & fees
14 Sept - 15 Sept
Agriturismo Podere Ristella - Wine&Food
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.
View all properties

Top Roccastrada Hotel Reviews

Castello di Leonina Relais

Castello di Leonina Relais

10/10 Excellent
"We stayed 4 days and are so glad we stayed here. The area has a restaurant right outside with the best view where they serve lunch and dinner. They also have a bar and a pool. It’s an old castle and yet they keep it clean and pretty restored. Breakfast buffet in the morning was included for us. The bathroom comment from others might be from not understanding how to use it as you have to pump the button several times to flush. The staff was wonderful and helpful. They spoke English and some Spanish."
Mariela 4-night trip
Posted 2 days ago
Castello di Leonina Relais
Hotel Italia

Hotel Italia

10/10 Excellent
"Staff were most courteous, both at front desk (local map offered on checkin) and in breakfast room. Breakfast buffet offered plenty of choices. Room and bathroom clean and tidy. City attractions dispersed throughout city, but walking made them accessible."
Catherine 4-night trip
Posted 5 days ago
Hotel Italia
Fattoria La Principina Hotel & Congress

Fattoria La Principina Hotel & Congress

8/10 Good
"great facility but needs a general upgrade and remodeling"
Giuseppe 1-night trip
Posted 2 weeks ago
Fattoria La Principina Hotel & Congress
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 2 weeks ago
Castello di Velona Resort Thermal SPA & Winery
Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel

10/10 Excellent
"Las habitaciones son super lindas y espaciosas. El desayuno es completo y variado. Estuve con mi familia muy a gusto. Fue una estancia placentera. Lo recomiendo."
patricia 3-night trip
Posted 1 month ago
Mercure Petriolo Siena Terme Spa Hotel
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 1 month ago
Castiglion del Bosco, A Rosewood Hotel

Frequently asked questions

What's it like visiting Roccastrada?
If spending time by the pool is your idea of the perfect getaway, you may want to explore historic Roccastrada, which has 12 places to stay with pools. During your visit, you can explore sights such as I Canaloni del Torrente Farma and Podere Ristella Vineyards and Winery, and then kick back and relax poolside at one of the accommodation options in Roccastrada that guests like for their pools.
What are some accommodation options with pools in Roccastrada?
Hotel Athena: Provides 2 outdoor swimming pools, an indoor pool and 3 restaurants. Grand Hotel Continental Siena – Starhotels Collezione: Offers buffet, a seasonal outdoor pool and free self parking. Castello di Velona Resort Thermal SPA & Winery: Features a children's pool, a seasonal outdoor pool and a private beach. Grand Hotel Bastiani: Offers 2 restaurants, 2 outdoor swimming pools and a full-service spa. Mastrojanni Relais - Small Luxury Hotels of the World: Hotel located near Piazza del Campo. Offers a rooftop terrace, a seasonal outdoor pool and a snack bar/deli.
How many pool hotels will I find in Roccastrada?
Expedia has 12 hotels in Roccastrada for your poolside break.
What is there to see and do in Roccastrada?
The picturesque setting of I Canaloni del Torrente Farma and Val di Merse showcase the area's natural beauty. Discover sights such as Podere Ristella Vineyards and Winery, Castello del Belagaio and Sassoforte Castle during your stay.
When is the best time to book a hotel with a pool in Roccastrada?
You may want to think about a place to stay with an outdoor swimming pool if you're planning to visit Roccastrada in the hottest months of August, July or June, when the average temp is 23°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or March, when the average temp is 9°C.
What's the best way to travel around Roccastrada?
Knowing the transportation options in Roccastrada can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Roccastrada Station or Sticciano Station. Roccastrada might not have very many public transport options to choose from, so consider renting a car to explore more.