Montgomery Cottages - Vacation Rentals in Simignano

Agriturismo gli Arcangeli From US $103
         

|
9.4 (60 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • Designated Smoking Area
Il Nespolo by Interhome From US $195
         

9.6 (10 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Stunning apartment in Ancaiano From US $174
         

8.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Pool
La Ginestra by Interhome From US $142
         

4.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Pool

Luxury Places to Stay in Simignano

Over 224+ Luxury Places to Stay in or Near Simignano
Villa Rock Cerbaia From US $4,741
         

New
Villa
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
La Capriata From US $4,618
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating
The Bishop Apartment From US $3,466
         

New
Apartment
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Honeymoon Room From US $2,314
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
The Casina From US $1,498
         

New
Villa
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
The Casina From US $1,178
         

|
New
Villa
  • Air Conditioner
  • Parking
  • Pool
The Tower Room From US $1,162
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating

Top-Rated Vacation Rentals with a Pool in Simignano

Over 175+ Top-Rated Vacation Rentals with a Pool in or Near Simignano
"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking From US $688
         

10.0 (11 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Le Caggia From US $611
         

|
10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
L'Ovile 8, Emma Villas From US $995
         

|
10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
Holiday Home Il Boschetto by Interhome From US $290
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
AgritourismoAzienda Villa Cennina From US $263
         

|
10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool
Podere La Castellina From US $152
         

|
9.8 (51 Reviews)
Apartment
  • Parking
  • Pool
  • View
Podere Casetta Entire Property in Exclusive Use Siena From US $581
         

|
9.7 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Borgo dei Fondi From US $111
         

|
9.6 (114 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Simignano

Over 135+ Pet-Friendly Vacation Rentals in or Near Simignano
Agriturismo Il Caggio From US $106
         

|
9.4 (88 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Le Mascie Country House From US $234
         

9.2 (9 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Beautiful apartment in Casole d'Elsa From US $394
         

Il Boschetto by Interhome From US $348
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Simignano

Over 40+ Large Vacation Homes & Villas in or Near Simignano
Villa Rosa From US $287
         

|
10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Holiday Villa in Tuscany – Exclusive Rental with Garden & Jacuzzi From US $300
         

10.0 (7 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Designated Smoking Area
9- Villa La Quercia From US $431
         

10.0 (6 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Simignano

Over 6+ Wheelchair Accessible Vacation Homes in or Near Simignano
Agriturismo la Taverna Di Celsa From US $101
         

|
9.6 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Borgo Il Poggiaccio Residence From US $217
         

|
9.2 (464 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Agriturismo Poggio ai Legni From US $124
         

|
9.2 (133 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Ocabianca casa per le vacanze From US $171
         

|
8.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Mucellena From US $133
         

|
8.9 (190 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool

Simignano Vacation Rentals and Airbnb Places to Stay Under $200

Over 56+ Simignano Vacation Rentals and Airbnb Places to Stay Under $200
La Palazzina From US $141
         

|
9.4 (12 Reviews)
Villa
  • Parking
  • Pet Friendly
  • View
Borgo Il Poggiaccio From US $184
         

8.8 (65 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Instantly Bookable Vacation Homes in Simignano

Over 95+ Instantly Bookable Vacation Homes in or Near Simignano
Lovely apartment in Casole d'Elsa From US $297
         

Appartamento Ampio nel Borgo Medioevale From US $248
         

New
House
  • Parking
  • Pool
  • Designated Smoking Area
Apartment for family From US $213
         

New
House
  • Parking
  • Pool
  • Designated Smoking Area

About Simignano Vacation Rentals

With more than 233 Simignano vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Simignano.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Simignano, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Simignano. Places to stay near Simignano are 1022.48 ft² on average, with prices averaging US $453 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Simignano with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Simignano

Type Count
Holiday Apartments 108
Vacation Homes 70
Villas 34
Cottages 10
Others 7
B&B 1
Hotels 1
Resorts 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Simignano

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Simignano.

Weather in Simignano

View the weather forecast for Simignano before booking your Simignano Vacation Rentals to confirm your best time to go.

December - February
High       Low
March - May
High       Low
June - August
High       Low
September - November
High       Low

Simignano Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Simignano?
How many vacation rentals are available in Simignano?

Currently, the total number of properties listed in 2026 is over 233 in the Simignano area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Simignano.