Hotels with a Pool in Montaione

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Nov 15 - Nov 16
Tomorrow
Nov 16 - Nov 17
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Hotels with a Pool in Montaione

A pool area with lounge chairs and umbrellas, surrounded by neatly trimmed hedges and trees.

1. Borgo san Benedetto

Borgo san Benedetto
Montaione
  • 2 outdoor pools
  • Pool loungers
9.6 out of 10, Exceptional, (57 reviews)
Sparkling outdoor pools invite guests to splash and unwind amid garden surroundings at this Colonial retreat. Families appreciate the dedicated children's pool, while active travelers enjoy tennis, basketball, and volleyball facilities.
The price is $157
$179 total
includes taxes & fees
Dec 2 - Dec 3
Borgo san Benedetto
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

2. Villa Sestilia

Villa Sestilia
Montaione
  • 2 outdoor pools
  • Children's pool
9.6 out of 10, Exceptional, (19 reviews)
Poolside paradise awaits at this rural villa, where two shimmering pools and a children's pool promise refreshing dips between tennis matches. Families appreciate the playground, while foodies savor Casa Masi's local cuisine under the Tuscan sky.
The price is $144
$161 total
includes taxes & fees
Dec 8 - Dec 9
Villa Sestilia
A person relaxing in a swimming pool with a view of rolling hills and greenery.

3. Castelfalfi

Castelfalfi
5.0 star property
Montaione
  • Poolside bar
  • Pool loungers
  • Full-service spa
9.6 out of 10, Exceptional, (194 reviews)
Swimming sessions sparkle at this vineyard-adjacent luxury hotel, where the seasonal outdoor pool offers summer relaxation with cold drinks served poolside. After swimming, guests enjoy facials at the spa or explore nearby hiking trails.
The price is $809
$901 total
includes taxes & fees
Nov 28 - Nov 29
Castelfalfi
A pool area with clear blue water, surrounded by neatly trimmed hedges and tall trees.

4. Villa Lena

Villa Lena
Palaia
  • 3 outdoor pools
  • Poolside bar
  • Pool loungers
9.8 out of 10, Exceptional, (16 reviews)
The price is $220
$245 total
includes taxes & fees
Nov 21 - Nov 22
Villa Lena
A pool area with a view of vineyards and rolling hills.

5. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (389 reviews)
Swimming among vineyards becomes reality across 3 spectacular outdoor pools surrounded by Tuscan countryside. Farm-fresh meals, wine tastings from the attached winery, and nearby medieval towns complete an idyllic Italian retreat.
The price is $107
$124 total
includes taxes & fees
Nov 26 - Nov 27
Poderi Arcangelo
A swimming pool with a sunshade, lounge chairs, and a building with arched windows.

6. Hotel Le Renaie

Hotel Le Renaie
3.0 star property
San Gimignano
  • Pool loungers
8.8 out of 10, Excellent, (34 reviews)
Splash into vacation mode at the seasonal outdoor pool surrounded by Tuscan countryside. Kids have their own dedicated pool while adults lounge under umbrellas. After swimming, explore nearby hiking trails or rent bicycles for mountain adventures.
The price is $145
$166 total
includes taxes & fees
Dec 5 - Dec 6
Hotel Le Renaie
A swimming pool with lounge chairs, a stone building, and a clear blue sky.

7. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (66 reviews)
Poolside paradise awaits at this Italian country B&B where seasonal outdoor swimming meets vineyard views. Travelers refresh with local wines, explore nearby hiking trails on rental bikes, and unwind on sun loungers until sunset.
The price is $91
$106 total
includes taxes & fees
Nov 20 - Nov 21
Il Castagnolo Country B&B
A villa with a swimming pool, surrounded by lush greenery and hills.

8. Relais Sassa al Sole

Relais Sassa al Sole
San Miniato
  • Poolside bar
  • Pool loungers
  • Hot tub
9.8 out of 10, Exceptional, (57 reviews)
Mountain adventure meets poolside relaxation at this Belle Époque farm stay. Seasonal swimming, a steamy hot tub, and pampering massage services create perfect recovery after horseback riding or mountain biking excursions.
The price is $218
$240 total
includes taxes & fees
Nov 22 - Nov 23
Relais Sassa al Sole
A pool area with lounge chairs and umbrellas, a view of a hilltop town with historic buildings.

9. Cappuccina Country Resort

Cappuccina Country Resort
4.0 star property
San Gimignano
  • Poolside bar
  • Pool umbrellas
8.8 out of 10, Excellent, (109 reviews)
Poolside bliss awaits with a seasonal outdoor retreat featuring umbrellas for shade and a cocktail bar. Steps from Piazza Duomo, this hotel also delights with garden views, free gourmet breakfasts, and hiking trails nearby.
The price is $186
$212 total
includes taxes & fees
Nov 20 - Nov 21
Cappuccina Country Resort
A view of a swimming pool with lounge chairs, surrounded by greenery and tall trees, with a building in the background.

10. Mormoraia

Mormoraia
San Gimignano
  • Poolside bar
  • Full-service spa
9.6 out of 10, Exceptional, (234 reviews)
Swimming sessions amid rolling vineyards define this rural retreat's seasonal outdoor pool experience. After laps, guests sip local wines at the poolside bar, then indulge in massages at the full-service spa or explore trails on rented bicycles.
The price is $298
$333 total
includes taxes & fees
Nov 16 - Nov 17
Mormoraia
A pool area with lounge chairs and umbrellas, surrounded by cypress trees and a vineyard in the background.

11. Tenuta Bartoli

Tenuta Bartoli
San Gimignano
  • Poolside bar
  • Pool loungers
10.0 out of 10, Exceptional, (2 reviews)
The price is $451
$502 total
includes taxes & fees
Dec 1 - Dec 2
Tenuta Bartoli
A stone building with a swimming pool, outdoor seating, and a hillside backdrop.

12. Agriturismo Il Casolare di Bucciano

Agriturismo Il Casolare di Bucciano
San Gimignano
  • Pool
  • Free parking
  • Free WiFi
  • Restaurant
  • Connecting rooms available
  • Air conditioning
9.6 out of 10, Exceptional, (103 reviews)
Farm life meets pool bliss at this Tuscan retreat, where seasonal swimming complements garden strolls. After exploring nearby attractions, guests can dine at the on-site restaurant, creating an authentic countryside escape.
The price is $114
$131 total
includes taxes & fees
Nov 20 - Nov 21
Agriturismo Il Casolare di Bucciano
A stone building with a swimming pool, outdoor seating, and a waterfall feature.

13. Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery
San Gimignano
  • Poolside bar
  • Pool loungers
9.8 out of 10, Exceptional, (79 reviews)
Sip handcrafted cocktails at the poolside bar while soaking up scenic rural views. This farm stay delights with delicious breakfast buffets featuring fresh orange juice, and offers wine tastings at its attached winery.
The price is $150
$171 total
includes taxes & fees
Nov 27 - Nov 28
Tenuta Sovestro - Agriturismo e Winery
A balcony with a view of the sunset, a pool, and a metal container with rocks.

14. Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
3.0 star property
San Gimignano
  • Full-service spa
9.6 out of 10, Exceptional, (55 reviews)
The price is $225
$254 total
includes taxes & fees
Dec 12 - Dec 13
Hotel Torciano Vecchio Asilo
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

15. Hotel Sovestro

Hotel Sovestro
3.0 star property
San Gimignano
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (350 reviews)
Splashing in dual outdoor pools surrounded by Tuscan countryside vistas creates unforgettable moments at this winery-adjacent hotel. Poolside bar service, sun loungers, and umbrellas enhance the experience while hiking trails beckon beyond.
The price is $130
$150 total
includes taxes & fees
Nov 16 - Nov 17
Hotel Sovestro
A swimming pool surrounded by a grassy area with trees and a hill in the background.

16. Fattoria San Donato

Fattoria San Donato
San Gimignano
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (65 reviews)
The price is $143
$163 total
includes taxes & fees
Nov 19 - Nov 20
Fattoria San Donato
An aerial view of a villa with a swimming pool, surrounded by lush greenery and terraced gardens.

17. Borgo Di Colleoli Resort

Borgo Di Colleoli Resort
Palaia
  • 2 outdoor pools
  • Pool loungers
9.0 out of 10, Wonderful, (106 reviews)
Poolside paradise awaits at Borgo Di Colleoli Resort with 2 sun-drenched outdoor pools and a children's splash zone. After swimming, guests savor regional cuisine at I Secoli restaurant or explore nearby mountain biking trails.
The price is $82
$95 total
includes taxes & fees
Nov 16 - Nov 17
Borgo Di Colleoli Resort
A swimming pool with lounge chairs and umbrellas, surrounded by grass and trees, with a view of distant hills.

18. Agriturismo La Palazzina

Agriturismo La Palazzina
Palaia
  • Pool loungers
8.4 out of 10, Very good, (26 reviews)
Splash into vacation mode at this Tuscan country house's rooftop pool, where sun loungers await after cycling adventures through scenic trails. Beach volleyball, bicycling rentals, and nearby hot springs complete the aquatic experience.
The price is $157
$181 total
includes taxes & fees
Nov 23 - Nov 24
Agriturismo La Palazzina
A pool area with a sunset view, surrounded by trees and a distant mountain range.

19. Le Mammole

Le Mammole
San Miniato
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
9.8 out of 10, Exceptional, (27 reviews)
The price is $95
$105 total
includes taxes & fees
Nov 16 - Nov 17
Le Mammole
A pool with a stone waterfall feature, surrounded by potted plants and greenery.

20. Torraccia di Chiusi

Torraccia di Chiusi
San Gimignano
  • Pool loungers
9.8 out of 10, Exceptional, (118 reviews)
Seasonal swimming beckons at this tranquil farm stay featuring both main and children's pools surrounded by umbrellas and loungers. Guests savor authentic Tuscan cuisine at the on-site restaurant while enjoying peaceful countryside serenity.
The price is $162
$184 total
includes taxes & fees
Nov 16 - Nov 17
Torraccia di Chiusi
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

Discover your perfect hotel with a pool in Montaione

Breakfast included
4 stars

Top landmarks in Montaione

Castelfalfi Golf Course

9.6/10 (11 reviews)
You might want to practice your swing at Castelfalfi Golf Course, a golf course located 0.5 mi (0.9 km) from central Castelfalfi.
See properties

About the destination

If you're looking to discover somewhere new, look no further than Montaione. Whether you're planning to stay for a night or for the week, the area around Montaione has accommodations to fit every need. Search for hotels in Montaione with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Montaione hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Montaione hotel deals are here with our lowest price guarantee.