Trips By Owner - Vacation Rentals in Pienza

Villa degli Archi From US $1,481
         

New
Villa
  • Pool
  • Child Friendly
  • Internet
L'Olmo From US $802
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Splendid farmhouse in the heart of the Val d'Orcia From US $1,329
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Villa in Monticchiello, your heaven in Tuscany From US $176
         

Beautiful independent Villa in Pienza From US $1,632
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa I Cipressini Tuscany Private luxury pool spa From US $1,613
         

10.0 (60 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Luxury Places to Stay in Pienza

Over 294+ Luxury Places to Stay in or Near Pienza
Piccolo Hotel La Valle From US $1,106
         

|
8.9 (1248 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere Manafiore From US $845
         

|
9.5 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
B&B Daria - Deb'S Monticchiello From US $819
         

|
9.4 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Il Giardino del Cardinale - Deb'S Monticchiello From US $802
         

|
9.2 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa I Cipressini piscina riscaldata spa Toscana From US $786
         

|
10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere Spedalone From US $779
         

|
9.0 (872 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Finestra dell'Angelo a Pienza From US $743
         

|
9.1 (9 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Accessibility
L'Olmo From US $710
         

|
9.8 (172 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Pienza

Over 123+ Top-Rated Vacation Rentals with a Pool in or Near Pienza
Terre di Nano From US $231
         

|
9.9 (19 Reviews)
House
  • Parking
  • Pool
  • TV
Agriturismo Cerreto From US $140
         

9.8 (272 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
La Saracina From US $517
         

9.8 (149 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Agriturismo Santa Maria From US $100
         

|
9.8 (69 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Agriturismo Collosodo From US $275
         

|
9.8 (5 Reviews)
House
  • Parking
  • Pool
  • View
Incanto b&b From US $144
         

|
9.7 (407 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pool
  • View
Poggiosalto in Toscana From US $165
         

|
9.7 (271 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Agriturismo Casalpiano From US $96
         

|
9.7 (153 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pienza

Over 112+ Pet-Friendly Vacation Rentals in or Near Pienza
Casa Bonari From US $90
         

|
10.0 (17 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Villa Loriana - Tuscan country villa with pool From US $1,129
         

Casa Gioia - Casa Olivieri From US $140
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • Bedding/Linens
  • Wellness Facilities
The house in the village - Angelica apartment - Vald'Orcia From US $122
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Iperbole country house, between Pienza and Montepulciano From US $1,642
         

10.0 (11 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
"Il Focolare" Superior Apartment in Monticchiello From US $118
         

10.0 (9 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 101+ Large Vacation Homes & Villas in or Near Pienza
Villa PoliFlora From US $74
         

|
10.0 (121 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Villa Rango From US $892
         

New
Villa
  • Child Friendly
Podere Manafiore - historical villa with swimming pool From US $969
         

Villa delle Fontane Amazing place for your holiday From US $502
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia From US $824
         

Wheelchair Accessible Vacation Homes in Pienza

Over 22+ Wheelchair Accessible Vacation Homes in or Near Pienza
Vento d’Orcia From US $164
         

|
9.9 (266 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Pienzalettings Guest House From US $165
         

New
House
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
Hotel Corsignano From US $195
         

|
9.4 (359 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Agriturismo Lunadoro From US $92
         

|
9.4 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hotel San Gregorio From US $239
         

|
9.4 (145 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tenuta Santo Pietro From US $197
         

|
9.3 (235 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hotel Relais II Chiostro di Pienza From US $136
         

|
8.8 (635 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Palazzo Massaini - Cavarciano From US $268
         

|
9.1 (536 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pienza Vacation Rentals and Airbnb Places to Stay Under $200

Over 108+ Pienza Vacation Rentals and Airbnb Places to Stay Under $200
Samsara Apartment From US $173
         

|
10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Sports/Activities
PienzaLettings Suites From US $133
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities
Amazing Panorama in Monticchiello From US $115
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Casa Bonari, amazing Tuscan view From US $172
         

10.0 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Elegant apartment with garden view and rooftop terrace From US $157
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Finestra Dell'Angelo From US $139
         

9.0 (2 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Pienza

Over 68+ Instantly Bookable Vacation Homes in or Near Pienza
Il Podere di Casa Rossa Pienza From US $274
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Samsara Apartment elegant apartment in the historical center. From US $211
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Podere Lamino with Swimming pool From US $220
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Apartment in Monticchiello with 2 bedrooms sleeps 4 From US $215
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Designated Smoking Area
  • TV
House with private pool with beautiful view Val d 'Orcia From US $339
         

9.8 (48 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Stunning apartment in Monticchiello with WiFi From US $244
         

9.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

About Pienza Vacation Rentals

With more than 303 Pienza vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Tripsbyowner 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 Tripsbyowner 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 1296.51 ft² on average, with prices averaging US $510 a night.

Tripsbyowner 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 108
Holiday Apartments 76
Villas 74
Others 18
Hotels 16
B&B 10
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Pienza

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

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

Currently, the total number of properties listed in 2026 is over 303 in the Pienza area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pienza.