Vacation Rentals in Fortress of Montestaffoli, San Gimignano: Compare 10+ Sites & Save

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  2. Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  San Gimignano
  6.  Fortress of Montestaffoli

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1222 Best Vacation Rentals in Fortress of Montestaffoli (Starting from $87)

La Casina tra le Torri
La Casina tra le Torri
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms4 Guests
9.2

Superb

47 reviews

$114
Average price / night
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Central  Romantic nest San Gimignano
Central Romantic nest San Gimignano
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV, Washer

2 Bedrooms4 Guests
New to Booking
$186
Average price / night
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Antica Posta
Antica Posta
House
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms5 Guests
8.8

Fabulous

10 reviews

$167
Average price / night
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La Rocca Romantica
La Rocca Romantica
Apartment
Via della Rocca 3, San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

Internet, Soundproof Room

New to Booking
$165
Average price / night
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Two Bedroom Apartment
Two Bedroom Apartment
Apartment
SAN GIMIGNANO, 53037, Italy
0.1k from Fortress of Montestaffoli center

Heater, Kitchen, No Smoking, Patio

2 Bedrooms4 Guests
New to Booking
$213
Average price / night
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I'Coco - Appartamento a San Gimignano
I'Coco - Appartamento a San Gimignano
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

2 Bedrooms3 Guests
9.2

Superb

8 reviews

$136
Average price / night
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Le Torri2 SanGimignanoApartments
Le Torri2 SanGimignanoApartments
Apartment
SAN GIMIGNANO, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$249
Average price / night
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Appartamento La Rocca
Appartamento La Rocca
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Guest Services, Balcony/Terrace, Internet, Security/Safety, Wellness Facilities, Fireplace/Heating

1 Bedroom2 Guests
9.3

Superb

26 reviews

$124
Average price / night
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IL PRUNELLO - a house between the towers
IL PRUNELLO - a house between the towers
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, Tennis Court

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$129
Average price / night
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Appartamento Le Rondini
Appartamento Le Rondini
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
9.4

Superb

9 reviews

$106
Average price / night
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Affittacamere Le Ginestre
Affittacamere Le Ginestre
House
Via di Quercecchio 57, San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

Internet, Laundry, No Smoking, TV

7.8

Good

6 reviews

$142
Average price / night
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Tusci Loft, A GEM in the CITY
Tusci Loft, A GEM in the CITY
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
8.5

Very Good

2 reviews

$121
Average price / night
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Panoramic apartment Il Borgo Antico in the city centre
Panoramic apartment Il Borgo Antico in the city centre
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Balcony, Barbecue, Heater, Internet, Kitchen, Laundry, Living Area, Patio

2 Bedrooms4 Guests
10.0

Exceptional

53 reviews

$138
Average price / night
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Martina House, Dome Square, San Gimignano, Wifi
Martina House, Dome Square, San Gimignano, Wifi
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$148
Average price / night
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San Gimignano Town Garden - 4 pax
San Gimignano Town Garden - 4 pax
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Washer

2 Bedrooms4 Guests
7.6

Good

4 reviews

$316
Average price / night
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CoZy House San Gimignano in the heart of Tuscany
CoZy House San Gimignano in the heart of Tuscany
Apartment
Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
10.0

Exceptional

6 reviews

$268
Average price / night
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San Gimignano Town Garden - 8 pax
San Gimignano Town Garden - 8 pax
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Washer

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$547
Average price / night
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Casa al Cerchio - Luxury Apartment With View & Free Private Parking
Casa al Cerchio - Luxury Apartment With View & Free Private Parking
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Luxury, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
9.3

Superb

4 reviews

$271
Average price / night
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San Gimignano Town Garden - 10 pax
San Gimignano Town Garden - 10 pax
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Washer

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$656
Average price / night
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Tusci Loft San Gimignano A GEM in the CITY
Tusci Loft San Gimignano A GEM in the CITY
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Self-catering

1 Bedroom4 Guests
8.3

Very Good

10 reviews

$228
Average price / night
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The Penthouse of Dreams
The Penthouse of Dreams
Apartment
san gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Balcony, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$170
Average price / night
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Casa dell Erbe
Casa dell Erbe
Apartment
San Gimignano, Italy
0.1k from Fortress of Montestaffoli center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms6 Guests
9.1

Superb

12 reviews

$103
Average price / night
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I'Quercecchio Relax with Sauna - In the Historic Center of SamGimignano
I'Quercecchio Relax with Sauna - In the Historic Center of SamGimignano
Apartment
San Gimignano, 53037, Italy
0.1k from Fortress of Montestaffoli center

AC, Breakfast Available, Free Parking, Heater, Internet, Kitchen, Laundry, Spa, TV

1 Bedroom2 Guests
8.0

Good

2 reviews

$176
Average price / night
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Apartment in the historic center
Apartment in the historic center
Apartment
San Gimignano, 53037, Italy
0.2k from Fortress of Montestaffoli center

AC, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, TV, Washer

1 Bedroom4 Guests
New to Booking
$87
Average price / night
Check Availability
The Artists' Tower 4 - Amazing view from the tower
The Artists' Tower 4 - Amazing view from the tower
Apartment
San Gimignano, 53037, Italy
0.2k from Fortress of Montestaffoli center

AC, Balcony, Heater, Internet, Kitchen, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$426
Average price / night
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The Artists' Tower - 6 Pax
The Artists' Tower - 6 Pax
Apartment
San Gimignano, 53037, Italy
0.2k from Fortress of Montestaffoli center

Laundry, No Smoking

3 Bedrooms6 Guests
New to Booking
$564
Average price / night
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House in the Court with panoramic balcony, wifi garage
House in the Court with panoramic balcony, wifi garage
Apartment
San Gimignano, 53037, Italy
0.2k from Fortress of Montestaffoli center

Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$278
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Fortress of Montestaffoli.

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Frequently Asked Questions

You can explore 1222 verified vacation rentals in Fortress of Montestaffoli. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Fortress of Montestaffoli vary depending on the season, property size, and location. Rates typically start from around $87 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Fortress of Montestaffoli include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Fortress of Montestaffoli welcome pets. Currently, 34 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Fortress of Montestaffoli often include amenities such as Fireplace/Heating, Wellness Facilities, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.