Title: Book the Best Hotels with POOL in Montegrossi in 2026 | Expedia.ca

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## Check availability on Montegrossi Hotels with a Pool

Tonight

[Feb 16 - Feb 17](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2026-02-16&endDate=2026-02-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 17 - Feb 18](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2026-02-17&endDate=2026-02-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Montegrossi hotels with a pool

![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/00571ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/0cec1f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, Italian cuisine](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/1f290a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/f0b9ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Sabolini

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information)

Colle di Val d'Elsa

9.2/10

Wonderful

(189 reviews)

"Beautiful location and hotel Staff were excellent - thank you"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Amit

CA $134

CA $154 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/f3280e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room (Castello La Leccia)](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/7ab2e5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | Private kitchen](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/6b1a0f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/28db0eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello La Leccia

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-La-Leccia.h4985032.Hotel-Information)

Castellina in Chianti

10/10

Exceptional

(96 reviews)

"Very beautiful property. Staff is very welcoming and professional."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

haluk

CA $245

CA $276 total

includes taxes & fees

Mar 13 - Mar 14

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-La-Leccia.h4985032.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/467add1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/a2b58103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/cd4b8baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/6123c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Tornano Wine Resort

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information)

Gaiole in Chianti

9.0/10

Wonderful

(100 reviews)

"Most beautiful stay with lovely staff"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Matthew

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information)

![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/6055a736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Cassia di Baccano

[](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

Loro Ciuffenna

9.4/10

Exceptional

(23 reviews)

"The staff were great and the villa was amazing"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ralphvincent

CA $219

CA $241 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/23000000/22240000/22239500/22239492/018686d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room](https://images.trvl-media.com/lodging/23000000/22240000/22239500/22239492/39dcf7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/23000000/22240000/22239500/22239492/0ce9121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms, Patio | Terrace/patio](https://images.trvl-media.com/lodging/23000000/22240000/22239500/22239492/9d311563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Agriturismo il Poggiarello

[](https://www.expedia.ca/Siena-Hotels-Agriturismo-Il-Poggiarello.h22239492.Hotel-Information)

Siena

9.4/10

Exceptional

(22 reviews)

"Mariangela, the hostess was so kind and attentive. Sara took care of our rooms and wonderful breakfasts everyday. This property has amazing views of the Siena/Tuscan courtside and an amazing pool that was so beautiful. Had no trouble getting a taxi to explore the area. Can't wait to come visit again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen

CA $295

CA $332 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Siena-Hotels-Agriturismo-Il-Poggiarello.h22239492.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a64418f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, body treatments, body wraps, body scrubs](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a7311095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/e1962a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/d186b654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### B&B Le Dimore Mezza Costa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

San Casciano in Val di Pesa

9.4/10

Exceptional

(25 reviews)

"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Raymundo

CA $106

CA $123 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/089cca52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/f5b61d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/afca094e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Garden view](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/eb7fec56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Meleto

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information)

Gaiole in Chianti

8.8/10

Excellent

(93 reviews)

"We had a great time"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anna

CA $214

CA $249 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/29f2f09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/9c42f1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, 2 Bedrooms](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/88129386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello Vicchiomaggio

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information)

Greve in Chianti

9.4/10

Exceptional

(372 reviews)

"Very special treat to stay here. We hope to return "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Cheyenne

CA $243

CA $267 total

includes taxes & fees

Mar 13 - Mar 14

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/190e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Single Room](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/914c3e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/b53ae9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Pozzo di Sant'Andrea

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

Siena

9.8/10

Exceptional

(16 reviews)

"Great host, lovely place near Siena"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Prem

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118310000/118305000/118304951/44c7d92f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Heated floors](https://images.trvl-media.com/lodging/119000000/118310000/118305000/118304951/79f2dc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/119000000/118310000/118305000/118304951/9876a4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/119000000/118310000/118305000/118304951/8bae5f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One Belvedere Tuscany

[](https://www.expedia.ca/Poggibonsi-Hotels-One-Belvedere-Tuscany.h118304951.Hotel-Information)

Poggibonsi

CA $621

CA $690 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Poggibonsi-Hotels-One-Belvedere-Tuscany.h118304951.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&regionId=553248622859355230&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Choose what matters most at hotels with a pool in Montegrossi

Breakfast included

4 stars

Ocean view

5 stars

Hot tub

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_553248622859355230)

## Top Montegrossi Hotel Reviews

![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg)

### Hotel Athena

10/10 Excellent

"Great hotel, beautiful view and excellent service from the personnel. "

[](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg)

### Hotel Italia

10/10 Excellent

"Nice clean room. Close to train/bus station. Very good breakfast "

[](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information)

![Hotel Borgo San Luigi](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/69a3ac66_y.jpg)

### Hotel Borgo San Luigi

10/10 Excellent

"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "

[](https://expedia.ca/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information)

![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg)

### Hotel Borgo di Cortefreda Relais

10/10 Excellent

"The hotel and services exceeded my expectations."

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information)

![Dievole Wine Resort](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/3ab5a8f3_y.jpg)

### Dievole Wine Resort

10/10 Excellent

"The property was breath taking. Staff was amazing and accommodating. Wonderful experience. "

[](https://expedia.ca/Castelnuovo-Berardenga-Hotels-Dievole-Wine-Resort.h1115409.Hotel-Information)

![Castello di Spaltenna- Small Luxury Hotels of the World](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg)

### Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "

[](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information)

![Villa Ermellina Siena, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/b5937afa_y.jpg)

### Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Very nice hotel and beautiful hotel. My only complaint is that the king bed I stayed in was very lumpy - I do mean very.. otherwise great place. Good size gym. Clean. Very friendly service."

[](https://expedia.ca/Siena-Hotels-Hotel-Garden.h73208.Hotel-Information)

![Borgo Vescine](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8d2f3252_y.jpg)

### Borgo Vescine

10/10 Excellent

"This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. "

[](https://expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.Hotel-Information)

![Villa La Borghetta Resort](https://images.trvl-media.com/lodging/2000000/1590000/1588400/1588342/3a037802_y.jpg)

### Villa La Borghetta Resort

10/10 Excellent

"Beautiful experience!"

[](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-La-Borghetta-Resort.h1588342.Hotel-Information)

## Frequently asked questions

### What are some hotels with pools in Montegrossi?

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