Montegabbro Holiday Rentals

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 prices for these dates

Our top choices for Montegabbro holiday rentals

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$131
includes taxes & fees
14 Dec - 15 Dec
Tuscasì Aparthotel

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (148)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is AU$123
includes taxes & fees
26 Dec - 27 Dec
Chianti Village Morrocco

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is AU$321
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi

Camping Siena Colleverde

Camping Siena Colleverde
3.0 star property
Scacciapensieri
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma

"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Belforte
10.0 out of 10, Exceptional, (78)
"What an awesome place. Lovely house and backyard with pool. Leo is friendly , helpful and welcoming . Belforte is a small , quiet hilltop village but it is very accessible (by car) to other awesome spots- Siena, San Gimignano , Volterra and others. Highly recommended "
New Zealand
Adrian d.
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
San Gimignano
10.0 out of 10, Exceptional, (106)
"Great villa in a lovely location. We (8 adults and 2 children) really enjoyed our trip. It had everything we needed and a beautiful view from the pool! Thank you to Allesandro for helping us book things in the local area too. "
United Kingdom
Catherine T.
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is AU$134
includes taxes & fees
20 Dec - 21 Dec
La Casa di Ines

panoramica casa con piscina privata

panoramica casa con piscina privata
siena
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
The price is AU$264
includes taxes & fees
22 Dec - 23 Dec
panoramica casa con piscina privata

san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi
San Gimignano City Centre
9.6 out of 10, Exceptional, (36)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
The price is AU$255
includes taxes & fees
6 Jan - 7 Jan 2026
san gimignano apartment in historical center, courtyard and fast free wifi

Peaceful cottage in Tuscany with private pool

Peaceful cottage in Tuscany with private pool
Castelnuovo di Val di Cecina
8.8 out of 10, Excellent, (8)
"We had a fabulous stay in this Italian house in Toscany. Rooms are big, every room has his own bathroom. The swimming pool is clean and there are enough seats. There is a nice terrace for the ones who wants to stay in the shadow. The beds are great. The nice little village has 2 good restaurants where we had great nights out and is only 5 minutes away by car. Sienna is only 1h15 away. A nice lake at only 30 minutes! The only - point I can give is the kitchen which in our opinion hadn't enough...
France
Elise P.
Peaceful cottage in Tuscany with private pool

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano

Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden
Volterra
10.0 out of 10, Exceptional, (63)
"it was a great holiday, with a beautiful house, beautiful view and a very friendly welcome from Jurgen."
Netherlands
frank l.
Holiday house with private pool and fenced garden

Le Macine, a wonderful ancient restored watermill with Pool

Le Macine, a wonderful ancient restored watermill with Pool
Volterra
9.6 out of 10, Exceptional, (82)
"Clean and comfortable stay with lovely garden and pool, overall a great experience"
United Kingdom
Daniel A.
Le Macine, a wonderful ancient restored watermill with Pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Montegabbro Hotel Reviews

Find out more about Montegabbro

Everything you need to know about Montegabbro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montegabbro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montegabbro holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montegabbro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montegabbro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montegabbro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montegabbro holiday rentals we have selected for you start as low as AU$123 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montegabbro rentals

At Expedia, we put the best Montegabbro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montegabbro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montegabbro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montegabbro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Montegabbro?

Yes, there are holiday rentals close to the most popular sights in Montegabbro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Montegabbro has to offer?

Borgo Argiano: This holiday home rental outside of Montegabbro is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You can relax into your holiday with a garden and a library.

What can I see and do in Montegabbro?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Sentierelsa Trail. Sovestro in Poggio Winery and Museo del Cristallo di Colle di Val d'Elsa are a couple of places you'll find in the wider area.

What are holiday rentals like in Montegabbro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montegabbro. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.