Trip Italy - Vacation Rentals in San Gimignano

San Gimignano Apartment From US $138
         

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9.3 (33 Reviews)
Apartment
  • Child Friendly
  • Internet
Tenuta Guardastelle From US $221
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
San Gimignano - Panoramic garden and beautiful pool! From US $655
         

Nice apartment for 4 guests with WIFI, A/C, pool and TV From US $243
         

Villa in a panoramic position in San Gimignano From US $707
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in San Gimignano

Over 1134+ Luxury Places to Stay in or Near San Gimignano
Villa Arnilù From US $3,826
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Simone - San Gimignano ,Tuscany From US $3,398
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Simone - Luxury Villa with swimming pool From US $3,327
         

10.0 (16 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Simone by PosarelliVillas From US $2,637
         

Top-Rated Vacation Rentals with a Pool in San Gimignano

Over 678+ Top-Rated Vacation Rentals with a Pool in or Near San Gimignano
Torraccia di Chiusi From US $210
         

10.0 (100 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool
Agriturismo Il Segreto di Pietrafitta From US $354
         

10.0 (55 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool
Vittoriana 3 - Apartment with pool From US $102
         

10.0 (36 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in San Gimignano

Over 491+ Pet-Friendly Vacation Rentals in or Near San Gimignano
Appartamento Maria From US $193
         

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10.0 (9 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Casa Vacanze Le Case From US $127
         

9.0 (8 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Apartment Lari by Interhome From US $286
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Vineyard View by Interhome From US $1,050
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in San Gimignano

Over 262+ Large Vacation Homes & Villas in or Near San Gimignano
Villa La Francigena From US $765
         

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10.0 (7 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Sabrina From US $668
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Panizzi – Villa with private pool From US $982
         

9.4 (23 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Diletta - Farmhouse with private pool From US $408
         

9.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
San Gimignano Town Garden - 10 pax From US $669
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in San Gimignano

Over 48+ Wheelchair Accessible Vacation Homes in or Near San Gimignano
Unique TWIN TOWER, an exclusive medieval tower From US $302
         

New
Apartment
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
Tognazzi Casa Vacanze - Appartamento Due Archi From US $163
         

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10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
il Casale del Cotone From US $266
         

9.4 (145 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Agriturismo Il Segreto di Pietrafitta From US $129
         

|
9.9 (278 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hotel Sovestro From US $258
         

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9.6 (307 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Agriturismo Poggio Rotondo From US $188
         

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9.9 (150 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Hotel Leon Bianco From US $137
         

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9.4 (590 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Agriturismo Castello di Montauto From US $206
         

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9.7 (231 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

San Gimignano Vacation Rentals and Airbnb Places to Stay Under $200

Over 568+ San Gimignano Vacation Rentals and Airbnb Places to Stay Under $200
Casolar del Pellegrino From US $63
         

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9.0 (206 Reviews)
Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Internet
Il Podere Orto From US $121
         

10.0 (2 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Security/Safety
Edera cozy house in Tuscan village From US $170
         

Aurora apartment 100 m from the center From US $104
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Instantly Bookable Vacation Homes in San Gimignano

Over 529+ Instantly Bookable Vacation Homes in or Near San Gimignano
La Capanna - Apartment with pool From US $289
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Apartment 'Casa Vacanze Etrusco - Quercia' with Air Conditioning From US $260
         

Vittoriana 1 - Apartment with pool From US $219
         

9.8 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ovile - Apartment with pool From US $220
         

9.6 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Vittoriana 4 - Apartment with pool From US $210
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Il Cottage - Apartment with pool From US $227
         

9.6 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

About San Gimignano Vacation Rentals

With more than 1143 San Gimignano vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trip Italy 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 San Gimignano.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Trip Italy San Gimignano, 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 San Gimignano. Places to stay near San Gimignano are 867.13 ft² on average, with prices averaging US $334 a night.

Trip Italy makes it easy and safe to find and compare vacation rentals in San Gimignano 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 San Gimignano

Type Count
Holiday Apartments 562
Vacation Homes 266
Villas 150
Others 70
Hotels 46
B&B 39
Cottages 9

Use these Quick Filters to Find a Vacation Rental in San Gimignano

Pro Tip: Trip Italy makes it easy to compare the best listings on Trip Italy homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trip Italy 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 San Gimignano.

Weather in San Gimignano

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

December - February
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March - May
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June - August
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September - November
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San Gimignano Vacation Rental Frequently Asked Questions

What are the top vacation rentals in San Gimignano?
How many vacation rentals are available in San Gimignano?

Currently, the total number of properties listed in 2026 is over 1143 in the San Gimignano area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in San Gimignano.