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Montegabbro Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montegabbro vacation rentals

A garden with a stone pathway, wooden benches, and various potted plants.

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is AED 517
AED 589 total
includes taxes & fees
28 Oct - 29 Oct
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. 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 AED 464
AED 518 total
includes taxes & fees
1 Nov - 2 Nov
Palazzo Pacini
A reception desk with the word "SPORTLAND" prominently displayed.

3. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is AED 166
AED 190 total
includes taxes & fees
11 Oct - 12 Oct
Sportland
An open wooden door leading to an outdoor patio with a table and chairs.

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 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 AED 391
AED 555 total
includes taxes & fees
2 Oct - 3 Oct
Palazzo al Torrione 2
A narrow street with stone buildings, a tower, and an archway.

5. 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 AED 453
AED 519 total
includes taxes & fees
5 Oct - 6 Oct
Materia Rooms San Gimignano
A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 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 AED 481
AED 550 total
includes taxes & fees
23 Oct - 24 Oct
B&B Palazzo Tortoli
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is AED 180
AED 210 total
includes taxes & fees
19 Oct - 20 Oct
Camping Boschetto Di Piemma
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

8. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is AED 612
AED 681 total
includes taxes & fees
8 Oct - 9 Oct
Riserva di Fizzano Residence
A table with breakfast items and a view of rolling hills.

9. 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 AED 267
AED 302 total
includes taxes & fees
26 Oct - 27 Oct
Chianti Village Morrocco
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

10. 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 AED 621
AED 695 total
includes taxes & fees
3 Oct - 4 Oct
Villa Montecastello
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

11. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 458
AED 524 total
includes taxes & fees
4 Oct - 5 Oct
Casa Vacanze Le Case
A building with a wooden door, windows with shutters, and flower boxes.

12. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is AED 272
AED 320 total
includes taxes & fees
1 Nov - 2 Nov
Donna Nobile
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

13. 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 AED 237
AED 377 total
includes taxes & fees
31 Oct - 1 Nov
Borgo Antico Residence
A stone building with outdoor seating and a view of the countryside.

14. 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 AED 630
AED 705 total
includes taxes & fees
11 Oct - 12 Oct
Antico Borgo Poggiarello
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

15. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is AED 347
AED 407 total
includes taxes & fees
25 Oct - 26 Oct
Villa San Filippo
Living area

16. La Rocca Romantica

La Rocca Romantica
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Very nice apartment with unbeatable location. in few steps up will take you to a nearby fortress and great view of the countryside and few steps down take you to the main plaza. hosts were also very friendly and helpful and available to help when needed."
United States
Sinava
The price is AED 530
AED 604 total
includes taxes & fees
2 Oct - 3 Oct
La Rocca Romantica
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

17. Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is AED 477
AED 537 total
includes taxes & fees
30 Oct - 31 Oct
Tenuta Quadrifoglio
A neatly made bed with a metal frame, two bedside tables with lamps, a wooden door, and a textured ceiling.

18. Charming San Gimignano Apartment With City Views

Charming San Gimignano Apartment With City Views
San Gimignano City Centre
The price is AED 982
AED 1,445 total
includes taxes & fees
13 Oct - 14 Oct
Charming San Gimignano Apartment With City Views
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

19. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
Ca' Bianca Tuscany Relais
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

20. 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 AED 429
AED 768 total
includes taxes & fees
14 Oct - 15 Oct
Borgo Il Poggiaccio
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.
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Top Montegabbro Hotel Reviews

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."
Elizabeth 1-night trip
Posted 14 hours ago
Fattoria di Vegi

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.