Montegabbro Vacation Rentals

Q: 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.

Dates

November 2026

December 2026

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Our top choices for Montegabbro vacation rentals

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

1. Palazzo Pacini

Colle di Val d'Elsa

John

￥19,352 total

includes taxes & fees

Dec 8 - Dec 9

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

2. Casa Vacanze Le Case

San Gimignano

Andrew

￥15,864 total

includes taxes & fees

Nov 12 - Nov 13

A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

3. Sportland

Colle di Val d'Elsa

Giorgio

￥8,722 total

includes taxes & fees

Nov 10 - Nov 11

A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.

4. Colle di Val d'Elsa - Siena - Apt Rose - B

Colle di Val d'Elsa

"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."

Tamara C.

￥23,373 total

includes taxes & fees

Nov 10 - Nov 11

A building with a wooden door, windows with shutters, and flower boxes.

5. Donna Nobile

San Gimignano City Centre

Treena

￥14,128 total

includes taxes & fees

Dec 8 - Dec 9

A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

San Gimignano City Centre

Caroline

￥17,915 total

includes taxes & fees

Dec 1 - Dec 2

A historic stone building with a prominent tower, arched windows, and a tiled roof.

7. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

￥19,161 total

includes taxes & fees

Nov 9 - Nov 10

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.

8. Tuscasì Aparthotel

Sovicille

Sergey

￥13,073 total

includes taxes & fees

Nov 20 - Nov 21

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

9. Tenuta Sant'Ilario

Gambassi Terme

Sergio

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

10. Borgo Antico Residence

Certaldo Alto

jane

￥16,008 total

includes taxes & fees

Nov 10 - Nov 11

A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

11. Tenuta Quadrifoglio

Gambassi Terme

Geraldine

￥22,781 total

includes taxes & fees

Nov 9 - Nov 10

An open wooden door leading to an outdoor patio with a table and chairs.

12. Palazzo al Torrione 2

San Gimignano City Centre

Klaus

￥20,136 total

includes taxes & fees

Nov 23 - Nov 24

A narrow alleyway with brick walls, wooden barrels, and potted plants.

13. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano City Centre

Glenn

￥26,490 total

includes taxes & fees

Nov 13 - Nov 14

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

14. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

￥19,249 total

includes taxes & fees

Dec 1 - Dec 2

A table with breakfast items and a view of rolling hills.

15. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

￥12,070 total

includes taxes & fees

Nov 9 - Nov 10

A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Sovicille

Sally

￥15,006 total

includes taxes & fees

Nov 15 - Nov 16

A vineyard with a stone building, a metal gate, and purple plants in the foreground.

17. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

San Gimignano City Centre

William

￥43,397 total

includes taxes & fees

Nov 11 - Nov 12

A modern bedroom with a bed, bedside tables, a bench, and artwork on the wall.

18. Vale's House

Certaldo

￥23,665 total

includes taxes & fees

Nov 9 - Nov 10

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

19. AlbergoDiffusoVolterra

Volterra

Mia

￥29,284 total

includes taxes & fees

Nov 9 - Nov 10

A patio with wicker furniture and potted plants, overlooking a scenic landscape.

20. Affittacamere Le Ginestre

San Gimignano City Centre

Jorge

￥17,150 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Montegabbro Hotel Reviews

A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.

Hotel Sovestro

San Gimignano

10/10 Excellent

Mikhail

A swimming pool, steps, and a grassy area with umbrellas.

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Fred

A yellow building with stone pillars, multiple windows, and a statue in the garden.

Villa San Lucchese

Poggibonsi

10/10 Excellent

Beautiful property with large rooms, parlors, great staff, great restaurant, etc. We arrived late and the kitchen was closed, but they made one call and re-opened it for us and served an amazing meal with late night enthusiasm on a beautiful deck. The rooms were large, nice baths and very comfortable beds. We wanted to stay another night to relax by the pool and enjoy the wonderful grounds, but they were booked so we had to move on as this was a last minute booking. Great breakfast in the...

Anonymous traveler

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

Villa Sabolini

Colle di Val d'Elsa

10/10 Excellent

Mark

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

Hotel Borgo San Luigi

Monteriggioni

10/10 Excellent

James

A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.

Hotel Le Colline

San Gimignano

10/10 Excellent

Federico

A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.

Relais Castel Bigozzi

Monteriggioni

10/10 Excellent

Tom

An outdoor dining area with tables and chairs, a brick wall, and a view of the landscape.

Hotel Il Castello

Certaldo Alto

10/10 Excellent

Kenneth

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

Hotel Ristorante La Dama nella Vigna

Monteriggioni

10/10 Excellent

Leigh

A stone staircase leading to a gated entrance, surrounded by lush greenery and a well-maintained lawn.

Tenuta Decimo

San Gimignano

10/10 Excellent

FLOR

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.

Albergo Etruria

Volterra

10/10 Excellent

Steve

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

Hotel Villa San Giorgio

Poggibonsi

10/10 Excellent

We had an excellent 1 night stay. The hotel is located in beautiful setting among the Tuscany hills with an easy 40 minutes drive south of Florence. IThe property sits an olive orchard directly below to a picture perfect Chianti vineyard. The views of the Tuscan hills at sunset and sunrise were spectacular. The registration process was quick and easy. The receptionist was friendly and helpful. He walked us to our room to make sure we were happy with our accomodations. Our room was spacious, the...

William

A hotel with a pool, outdoor seating, and a mountainous backdrop.

Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

10/10 Excellent

Nicest hotel that we stayed at in Italy. Exceptional service and they strive to be upscale and deliver. Impeccable views, grounds, rooms, and restaurant. Almost felt too nice to be true-- blend of older style with new updates. A bit Disney-fied in feel that it seems to cater to mostly Americans and few locals. However, this means no hassles, broken fixtures, etc. (but it is a very different feel like a California spa vs. an old Italy village hotel). Only minor note is that it is a bit removed...

Jerry

A building with multiple arched windows and doors, outdoor seating areas with tables and chairs, and potted plants.

Hotel Le Renaie

San Gimignano

10/10 Excellent

marley

A historic stone building with multiple arches and towers, featuring a central open courtyard with outdoor seating.

Hotel Leon Bianco

San Gimignano City Centre

10/10 Excellent

We loved this place! Getting here was a bit tricky, as the map we were given in the welcome email was of bad quality, so it didn't take us to the correct place right away, but we figured it out, very minor. I'm sure you can ask for a better quality map. When we arrived to check in, we were greeted by Lisa, who was oh so very helpful! She showed us where laundry was, asked all questions we had about WIFI and other hotel things, recommended us 3 terrific places to eat dinner on each of our 3...

Todd

A round table with a white tablecloth, surrounded by metal chairs, under a white umbrella.

Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

10/10 Excellent

Dorothy

Find out more about Montegabbro

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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.

Montegabbro Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montegabbro vacation rentals

1. Palazzo Pacini

2. Casa Vacanze Le Case

3. Sportland

4. Colle di Val d'Elsa - Siena - Apt Rose - B

5. Donna Nobile

6. B&B Palazzo Tortoli

7. Materia Rooms San Gimignano

8. Tuscasì Aparthotel

9. Tenuta Sant'Ilario

10. Borgo Antico Residence

11. Tenuta Quadrifoglio

12. Palazzo al Torrione 2

13. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

14. Antica Pieve B&B

15. Chianti Village Morrocco

16. Casa di Campagna in Toscana

17. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

18. Vale's House

19. AlbergoDiffusoVolterra

20. Affittacamere Le Ginestre

Find vacation rentals that suit your style

Top Montegabbro Hotel Reviews

Hotel Sovestro

10/10 Excellent

Find out more about Montegabbro

Frequently Asked Questions

Are there vacation rentals in Montegabbro?

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

What can I see and do in Montegabbro?

What are vacation rentals like in Montegabbro?