Hotels with Pool & Resorts in Monteriggioni from NZ$251

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Monteriggioni Hotels with Pool

Next weekend
In two weeks

Our top choices for Monteriggioni hotels with a pool

La Rocca della Magione

La Rocca della Magione
Monteriggioni
9.4 out of 10, Exceptional, (6)
"Lovely property in a 13th century convent. Situated on a hill overlooking a valley. Family owned, very sweet staff. Visitors (esp Americans) should know the owners speak little to no English, so come with your google translate or try and learn a little Italian prior. One major thing I learned in Italy is the importance of communicating your arrival plan with your host prior to arrival as many establishments are family owned and operated. Owner was very accommodating even though we were...
United States
Jennifer
La Rocca della Magione

Relais Castel Bigozzi

Relais Castel Bigozzi
4.0 star property
Monteriggioni
8.8 out of 10, Excellent, (242)
"Great location, facility, staff, views and restaurant. Ideal for seclusion. "
United States
Innokentiy
The price is NZ$251
includes taxes & fees
5 Jan - 6 Jan 2026
Relais Castel Bigozzi

Fattoria Lornano Winery

Fattoria Lornano Winery
Monteriggioni
8.0 out of 10, Very good, (5)
"The staff were so friendly and polite to us during our stay. Such a gem of a place to stay and we are very happy we chose to stay there "
Canada
Tamara
Fattoria Lornano Winery

Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (405)
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
United States
Allyson
Hotel Borgo San Luigi

Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (337)
"We enjoyed our stay"
United States
Joshua
Hotel Il Piccolo Castello

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Monteriggioni
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is NZ$697
includes taxes & fees
28 Dec - 29 Dec
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..

TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..
MONTERIGGIONI
8.0 out of 10, Very good, (1)
"Lovely home in a lovely area"
United States
jude d.
The price is NZ$806
includes taxes & fees
8 Jan - 9 Jan 2026
TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
MONTERIGGIONI
10.0 out of 10, Exceptional, (1)
"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "
United States
Anonymous traveller
The price is NZ$862
includes taxes & fees
28 Dec - 29 Dec
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

Lovely typical barn ,, in the heart of the most beautiful cities of Tuscany

Lovely typical barn ,, in the heart of the most beautiful cities of Tuscany
MONTERIGGIONI (SIENA)
Lovely typical barn ,, in the heart of the most beautiful cities of Tuscany

------ LA STALLA -----

------ LA STALLA -----
Monteriggioni
The price is NZ$899
includes taxes & fees
28 Dec - 29 Dec
------ LA STALLA -----
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.

Top Monteriggioni Hotel Reviews

Frequently asked questions

What's it like visiting Monteriggioni?
If laying by the pool is your idea of the perfect getaway, you may want to explore luxurious Monteriggioni, which offers 8 places to stay with pools. While you're here, you can explore attractions such as Alta Val d'Elsa River Park and Val di Merse, and then relax and unwind poolside at one of the accommodation options in Monteriggioni that guests like for their pools.
What are some accommodation options with pools in Monteriggioni?
Hotel Borgo San Luigi: Features a children's pool, a seasonal outdoor pool and a rooftop terrace. Hotel Athena: Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Borgo Grondaie: Features a full-service spa, an outdoor pool and a sauna. Villa La Borghetta Resort: Provides a children's pool, a seasonal outdoor pool and a full-service spa. Grand Hotel Continental Siena – Starhotels Collezione: Features a seasonal outdoor pool, an indoor pool and 2 restaurants.
How many hotels with pools will I find in Monteriggioni?
Expedia has 8 hotels in Monteriggioni for your poolside break.
What is there to see and do in Monteriggioni?
Surround yourself with nature at Alta Val d'Elsa River Park and Val di Merse. Discover sights such as San Leonardo al Lago during your stay. The countryside and wineries are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Monteriggioni?
You may want to consider accommodation that has an outdoor pool if you plan to visit Monteriggioni in the warmest months of August, July or June, when the average temperature is 22°C. Accommodation with an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 6°C.
What's the best way to travel around Monteriggioni?
Knowing the transportation options in Monteriggioni can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Monteriggioni Castellina Station or Monteriggioni Badesse Station. Monteriggioni might not have many public transport choices, so consider a car rental to maximise your time.

Explore a world of travel with Expedia