Default HTG hotel image

Montegabbro Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montegabbro vacation rentals

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is P9,382
P10,461 total
includes taxes & fees
Oct 25 - Oct 26
Palazzo Pacini
A garden with a stone pathway, wooden benches, and various potted plants.

2. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (87 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is P9,499
P10,801 total
includes taxes & fees
Oct 13 - Oct 14
Antico Borgo il Cardino
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

3. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is P3,339
P3,884 total
includes taxes & fees
Oct 26 - Oct 27
Camping Boschetto Di Piemma
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

4. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is P5,773
P6,701 total
includes taxes & fees
Nov 2 - Nov 3
Casa Vacanze Le Case
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

5. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is P6,624
P7,497 total
includes taxes & fees
Nov 1 - Nov 2
Tenuta Sant'Ilario
A swimming pool with clear water, surrounded by trees and umbrellas.

6. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is P5,728
P6,723 total
includes taxes & fees
Oct 21 - Oct 22
Villa San Filippo
A stone building with outdoor seating and a view of the countryside.

7. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is P10,651
P11,927 total
includes taxes & fees
Oct 12 - Oct 13
Antico Borgo Poggiarello
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

8. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is P4,007
P6,378 total
includes taxes & fees
Oct 15 - Oct 16
Borgo Antico Residence
A building with a wooden door, windows with shutters, and flower boxes.

9. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is P4,797
P5,629 total
includes taxes & fees
Nov 1 - Nov 2
Donna Nobile
A narrow street with stone buildings, a tower, and an archway.

10. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is P6,621
P7,635 total
includes taxes & fees
Nov 3 - Nov 4
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

11. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is P5,741
P8,426 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo al Torrione 2
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

12. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is P7,513
P13,260 total
includes taxes & fees
Oct 14 - Oct 15
Borgo Il Poggiaccio
A stone courtyard with a bench, potted plants, and a building in the background.

13. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is P6,356
P7,202 total
includes taxes & fees
Oct 18 - Oct 19
Casa di Campagna in Toscana
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,904
P5,209 total
includes taxes & fees
Nov 2 - Nov 3
Tuscasì Aparthotel
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

15. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is P11,221
P12,555 total
includes taxes & fees
Oct 24 - Oct 25
Villa Montecastello
A view from a window overlooking a rural landscape with fields and a distant mountain range.

16. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is P8,568
P9,777 total
includes taxes & fees
Oct 18 - Oct 19
B&B Palazzo Tortoli
A table with breakfast items and a view of rolling hills.

17. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is P4,997
P5,637 total
includes taxes & fees
Oct 15 - Oct 16
Chianti Village Morrocco
Outdoor pool

18. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is P8,348
P9,394 total
includes taxes & fees
Nov 9 - Nov 10
Residence Arianna
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

19. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is P12,248
P13,614 total
includes taxes & fees
Oct 19 - Oct 20
Riserva di Fizzano Residence
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montegabbro Hotel Reviews

Castelfalfi

Castelfalfi

10/10 Excellent
"Beautiful place to stay!"
Peter 3-night trip
Posted 6 hours ago
Castelfalfi

Find out more about Montegabbro

Search for holiday rentals in Montegabbro on Expedia! You can easily find your home rentals, villas, holiday apartments in Montegabbro using one of the methods below:

  • View our selection of featured holiday rentals in Montegabbro
  • Use the map to find apartments and other holiday homes in the Montegabbro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montegabbro while they last

Look no further and take a look at our great range of rental properties in Montegabbro!

Frequently asked questions

Are there vacation rentals in Montegabbro?

Yes, you can find vacation rentals near the most popular points of interest in Montegabbro, or you can choose a more secluded option if you'd like a relaxing place to stay.

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

Borgo Argiano: This vacation home rental outside of Montegabbro is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation 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 Val di Merse. Sovestro in Poggio Winery and Colle di Val d'Elsa Cathedral are a couple of places you'll find in the larger area.

What are vacation rentals like in Montegabbro?

Vacation rentals are private properties you can reserve for several days or more in Montegabbro. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.