Rolling hills, a winding road, and scattered trees.

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Check availability on Montaione Hotels with Pool

Our top choices for Montaione hotels with a pool

A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

1. Villa Sestilia

Villa Sestilia
Montaione
9.6 out of 10, Exceptional, (19 reviews)
  • cleanliness
    Dive into rural Tuscan relaxation with 2 refreshing outdoor pools, a children's pool, and tennis court for endless summer fun.
The price is £121
includes taxes & fees
8 Dec - 9 Dec
Villa Sestilia
A pool area with lounge chairs and umbrellas, surrounded by neatly trimmed hedges and trees.

2. Borgo san Benedetto

Borgo san Benedetto
Montaione
9.6 out of 10, Exceptional, (57 reviews)
  • cleanliness
    Splash into summer fun at this Colonial retreat with two refreshing pools and sport courts for all.
The price is £134
includes taxes & fees
3 Dec - 4 Dec
Borgo san Benedetto
An outdoor brick barbecue area with a wooden bench nearby.

3. Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!

Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!
Frazione Mura, Montaione
10.0 out of 10, Exceptional, (3 reviews)
The price is £149
includes taxes & fees
24 Nov - 25 Nov
Apartment with 2 bedrooms and 1 bathroom in the garden in Chianti!
A person relaxing in a swimming pool with a view of rolling hills and greenery.

4. Castelfalfi

Castelfalfi
5.0 star property
Montaione
9.6 out of 10, Exceptional, (194 reviews)
  • cleanliness
    Scenic seasonal pool with mountain views offers sun-drenched days surrounded by vineyard landscapes at this luxury hotel.
The price is £682
includes taxes & fees
28 Nov - 29 Nov
Castelfalfi
A rectangular swimming pool with clear blue water, surrounded by a tiled deck.

5. 2-BR 1 bath abode in the Chianti hills!

2-BR 1 bath abode in the Chianti hills!
Mura, Montaione
8.0 out of 10, Very good, (1 review)
The price is £149
includes taxes & fees
2 Dec - 3 Dec
2-BR 1 bath abode in the Chianti hills!
A pool area with clear blue water, surrounded by neatly trimmed hedges and tall trees.

6. Villa Lena

Villa Lena
Palaia
9.8 out of 10, Exceptional, (16 reviews)
The price is £203
includes taxes & fees
20 Nov - 21 Nov
Villa Lena
A pool area with a view of vineyards and rolling hills.

7. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
9.0 out of 10, Wonderful, (389 reviews)
  • cleanliness
    Splash into a Tuscan paradise with 3 sun-kissed pools at this charming winery farmstay.
The price is £94
includes taxes & fees
26 Nov - 27 Nov
Poderi Arcangelo
A swimming pool with a sunshade, lounge chairs, and a building with arched windows.

8. Hotel Le Renaie

Hotel Le Renaie
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (34 reviews)
  • cleanliness
    Tuscan escape with seasonal outdoor pool and children's splash area amid garden landscapes.
The price is £125
includes taxes & fees
6 Dec - 7 Dec
Hotel Le Renaie
A swimming pool with lounge chairs, a stone building, and a clear blue sky.

9. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
9.0 out of 10, Wonderful, (66 reviews)
  • cleanliness
    Stretch out poolside at this rustic country house, complete with seasonal outdoor pool, loungers, and refreshing bar service.
The price is £80
includes taxes & fees
20 Nov - 21 Nov
Il Castagnolo Country B&B
A stone building with a swimming pool, outdoor seating, and a hillside backdrop.

10. Agriturismo Il Casolare di Bucciano

Agriturismo Il Casolare di Bucciano
San Gimignano
9.6 out of 10, Exceptional, (103 reviews)
  • cleanliness
    Splash into the Tuscan countryside with a seasonal pool overlooking gardens at this rural farmstay.
The price is £99
includes taxes & fees
20 Nov - 21 Nov
Agriturismo Il Casolare di Bucciano
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.
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Choose what matters most at hotels with a pool in Montaione

Breakfast included
4 stars

Top Montaione Hotel Reviews

Castelfalfi

Castelfalfi

10/10 Excellent
"Best hotel in Tuscany. Everything is perfect."
Luis 3-night trip
Posted 14 hours ago
Castelfalfi
Tenuta Castellare di Tonda

Tenuta Castellare di Tonda

8/10 Good
"We thought they would be serving dinner every night but there was no chef! So no Dinner service. Good A/C. Breakfast buffet was great, bartender made sandwiches and salads at lunch time. Be prepared to drive windy dark roads at night to find restaurants, 10-20 minutes away. Also we were charged additional fees for early checkin and late checkout, I found this to be excessive. We found their local white wine is not very good (buttery, and perfumy)"
Richard 3-night trip
Posted 5 months ago
Tenuta Castellare di Tonda

Frequently asked questions

What's it like visiting Montaione?
If taking it easy by the pool is your idea of the perfect getaway, you might want to think about quaint Montaione, which offers 19 places to stay with pools. During your trip, you can explore sights such as Castelfalfi Golf Course and Casa del Boccaccio, and then relax and unwind poolside at one of the accommodation options in Montaione that guests like for their pools.
What are some hotels with pools in Montaione?
Castelfalfi: Features 4 restaurants, a seasonal outdoor pool and a full-service spa. Boccioleto Resort&Spa: Offers a sauna, a seasonal outdoor pool and a rooftop terrace. Tenuta Castellare di Tonda: Provides a children's pool, a seasonal outdoor pool and a full-service spa. Borgo san Benedetto: Features 2 outdoor swimming pools, a children's pool and a snack bar/deli. Calanchi Apartments: Offers a children's pool, an outdoor pool and a rooftop terrace.
How many hotels with pools will I find in Montaione?
Expedia's 19 hotels in Montaione give you a great choice for your poolside getaway.
What is there to see and do in Montaione?
Make a point to visit attractions such as Chianti Observatory and Il Fiaschetto. Discover sights such as Castelfalfi Golf Course during your stay.
When is the best time to book a hotel with a pool in Montaione?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Montaione in the warmest months of August, July or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is 7°C.