Owner Direct Vacation Rentals in Pienza

The Best Owner Direct Vacation Rentals in Pienza. Explore thousands of vacation home rentals, large cabins, and villas near Pienza

Villa PoliFlora From US $74
         

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10.0 (121 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Luxury Villa in Monticchiello, your heaven in Tuscany From US $121
         

L'Olmo From US $631
         

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10.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Villa I Cipressini Tuscany Private luxury pool spa From US $1,720
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Holiday Home Arpicella From US $142
         

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10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia From US $526
         

10.0 (44 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere FonteBernardi casa con vista su Pienza From US $196
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • TV

Luxury Places to Stay in Pienza

Over 287+ Luxury Places to Stay in or Near Pienza
Dimora Buonriposo Pienza Country House From US $2,272
         

Villa Lissa - Large villa with private pool From US $1,900
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Iperbole country house, between Pienza and Montepulciano From US $1,781
         

10.0 (11 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful independent Villa in Pienza From US $1,735
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa degli Archi From US $1,481
         

New
Villa
  • Pool
  • Child Friendly
  • Internet

Top-Rated Vacation Rentals with a Pool in Pienza

Over 123+ Top-Rated Vacation Rentals with a Pool in or Near Pienza
Vento Dorcia From US $183
         

10.0 (23 Reviews)
Other
  • Parking
  • Pool
  • Balcony/Terrace
Large Tuscany Villa rental near Pienza - southern Tuscany From US $881
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Villa with panoramic views of Pienza and Val d'Orcia From US $439
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lavender Apartment with a view of the Val d'Orcia From US $219
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Splendid farmhouse in the heart of the Val d'Orcia From US $995
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa I Cipressini piscina riscaldata spa Toscana From US $786
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pienza

Over 102+ Pet-Friendly Vacation Rentals in or Near Pienza
Dimora Segreta From US $179
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
The house in the village - Angelica apartment - Vald'Orcia From US $128
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa Gioia - Casa Olivieri From US $104
         

New
Apartment
  • Pet Friendly
  • Bedding/Linens
  • Wellness Facilities
La Bellavita B&B From US $119
         

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9.9 (246 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pet Friendly
  • TV
"Il Focolare" Superior Apartment in Monticchiello From US $136
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa Bonari From US $90
         

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9.9 (31 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
Vento d’Orcia From US $164
         

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9.8 (297 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Pienza on PetFriendly.io

Large Vacation Homes & Villas in Pienza

Over 102+ Large Vacation Homes & Villas in or Near Pienza
GARAGE47 Storica Officina Meccanica LOFT B&B iN PIENZA From US $184
         

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9.8 (335 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Terre di Nano From US $231
         

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9.8 (40 Reviews)
House
  • Parking
  • Pool
  • TV
Agriturismo Le Macchie From US $694
         

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9.8 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Poggiosalto in Toscana From US $165
         

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9.7 (276 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Villa Fonte Siena From US $1,113
         

Wheelchair Accessible Vacation Homes in Pienza

Over 27+ Wheelchair Accessible Vacation Homes in or Near Pienza
Tenuta Santo Pietro From US $197
         

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9.3 (235 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Pienzalettings Guest House From US $165
         

New
House
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
Hotel Corsignano From US $214
         

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9.4 (331 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Podere Spedalone From US $225
         

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9.1 (866 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Palazzo Massaini - Cavarciano From US $151
         

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9.1 (480 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Agriturismo Barbi From US $155
         

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9.1 (306 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Agriturismo Bagnolo From US $98
         

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9.0 (228 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Agriturismo il Casato Mag-il Vaglio From US $245
         

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9.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • View

Pienza Varoom and Airbnb Places to Stay Under $200

Over 112+ Pienza Varoom and Airbnb Places to Stay Under $200
La Sesta Luna From US $110
         

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9.9 (20 Reviews)
Apartment
  • Security/Safety
  • Sports/Activities
  • Wellness Facilities
TuscanyLettings Studio&Room From US $107
         

10.0 (1 Review)
House
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities
Residenza d'Epoca La Rosa From US $144
         

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9.8 (208 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Amazing Panorama in Monticchiello From US $117
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Agriturismo La Casellina From US $128
         

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9.8 (85 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Affitto casa in Val d'Orcia From US $184
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
OgniVolta From US $170
         

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9.8 (68 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

Instantly Bookable Vacation Homes in Pienza

Over 82+ Instantly Bookable Vacation Homes in or Near Pienza
Il Podere di Casa Rossa Pienza From US $300
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa Bonari, amazing Tuscan view From US $154
         

10.0 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Elegant apartment with garden view and rooftop terrace From US $128
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
A very comfortable apartment in Tuscan style From US $163
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Finestra Dell'Angelo From US $161
         

10.0 (1 Review)
Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
Piccola Corte - an all flat apartment downtown Cortona From US $90
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Accessibility
Stunning apartment in Monticchiello From US $154
         

9.0 (7 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV

About Pienza Vacation Rentals

With more than 296 Pienza vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 Pienza.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Pienza, 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 Pienza. Places to stay near Pienza are 1327.71 ft² on average, with prices averaging $477 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Pienza 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 Pienza

Type Count
Vacation Homes 100
Holiday Apartments 74
Villas 72
Others 24
Hotels with Suites 16
B&B 9
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Pienza

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

Weather in Pienza

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

December - February
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