Title: Montepulciano Vacation Rentals from CA $109: Short-Term Rentals for 2026 | Expedia.ca [Montepulciano Travel Guide](https://expedia.ca/Montepulciano.dx601351)[Hotels in Montepulciano](https://expedia.ca/Montepulciano-Hotels.d601351.Travel-Guide-Hotels)[Flights to Montepulciano](https://expedia.ca/Cheap-Flights-To-Montepulciano.d601351.Travel-Guide-Flights)[Things to do in Montepulciano](https://expedia.ca/Things-To-Do-In-Montepulciano.d601351.Travel-Guide-Activities)[Montepulciano Car Rentals](https://expedia.ca/Car-Rentals-In-Montepulciano.d601351.Car-Rental-Guide)[Montepulciano Vacation Packages](https://expedia.ca/Montepulciano.d601351.Destination-Travel-Guides) ![Montepulciano featuring landscape views, heritage architecture and a city](https://images.trvl-media.com/place/601351/8e058793-a90b-4fbe-bc1c-fe0b632a5e96.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Montepulciano Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=601351&startDate=2025-12-14&endDate=2025-12-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=601351&startDate=2025-12-15&endDate=2025-12-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=601351&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=601351&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montepulciano vacation rentals ![Lobby](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/c477a48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) 8.8/10 Excellent (94) "gorgeous historical property, very attentive host, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $121 CA $139 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/18007833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/4add3036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/302bfcfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/8e818071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) 6.0/10 (1) "Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JON CA $137 CA $158 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/3e489ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/6fa7b9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/e6496db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, City View](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/fe06c21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Il-Tosco.h6309554.Hotel-Information) 10/10 Exceptional (115) "The staff was courteous, the food was amazing, and the location was great. We were very impressed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua CA $340 CA $381 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Montepulciano-Hotels-Il-Tosco.h6309554.Hotel-Information) ![Standard Room | Exterior](https://images.trvl-media.com/lodging/3000000/2700000/2693300/2693210/fb4e1aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Hill View](https://images.trvl-media.com/lodging/3000000/2700000/2693300/2693210/w828h624x0y17-c0979e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/3000000/2700000/2693300/2693210/9eeca699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/3000000/2700000/2693300/2693210/310f9e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Osteria-Del-Borgo.h2693210.Hotel-Information) 9.0/10 Wonderful (156) "Staff and location were both excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas [](https://www.expedia.ca/Montepulciano-Hotels-Osteria-Del-Borgo.h2693210.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129322/dd3331e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129322/bbf478c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129322/w850h564x0y1-c4fad8d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129322/80e53474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-INDEPENDENT-HOUSE-LARGE-TERRACES-SPECTACULAR-VIEWS-In-CENTER-W-PARKING.h19129322.Hotel-Information) 9.6/10 Exceptional (82) "This house and location was perfect. Beautiful views and a great kitchen. Montepulciano was our favorite town that we visited on our trip. Easy check in and the host had a document that she sent us that had a lot of great info." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom K. [](https://www.expedia.ca/Montepulciano-Hotels-INDEPENDENT-HOUSE-LARGE-TERRACES-SPECTACULAR-VIEWS-In-CENTER-W-PARKING.h19129322.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/29000000/28770000/28764700/28764637/332e73d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/29000000/28770000/28764700/28764637/b3498baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/29000000/28770000/28764700/28764637/005fb74b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms](https://images.trvl-media.com/lodging/29000000/28770000/28764700/28764637/9e573a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Panoramic-Villa-Surrounded-By-Vineyards-And-Olive-Groves.h28764637.Hotel-Information) 9.6/10 Exceptional (4) "My two friends and I enjoyed our stay at San Bono. The highlight was having the family make and serve us an authentic Tuscan meal! The view is amazing and the location was perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Flourish Flowers [](https://www.expedia.ca/Montepulciano-Hotels-Panoramic-Villa-Surrounded-By-Vineyards-And-Olive-Groves.h28764637.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/28000000/27330000/27320200/27320167/w1920h1276x0y0-56777f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27330000/27320200/27320167/w1920h1277x0y0-16831f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27330000/27320200/27320167/w1917h1276x0y0-643bbab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27330000/27320200/27320167/w1920h1277x0y0-19e68a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Typical-Villa-With-Private-Pool-Situated-In-A-Panoramic-Position-In-Southern-Tuscany.h27320167.Hotel-Information) 10/10 Exceptional (2) "The villa is spacious with big bedrooms and five good bathrooms. The kitchen is well equipped and our big family with 8 adults and 6 children had everything we needed for our 14-day stay. There is a big pool beautifully located in a separate part of the garden. The trees and bushes give shadow all through the day so there is no need for umbrellas. The whole property is well cared for by the very friendly owners who live nearby. This is a perfect location for a visit in Toscana, close to many... ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Kristina M. [](https://www.expedia.ca/Montepulciano-Hotels-Typical-Villa-With-Private-Pool-Situated-In-A-Panoramic-Position-In-Southern-Tuscany.h27320167.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18780000/18770500/18770474/0171edae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/19000000/18780000/18770500/18770474/de823e27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18780000/18770500/18770474/28a65910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18780000/18770500/18770474/w2272h1486x0y0-d2766dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-Charming-House-In-The-Heart-Of-Montepulciano.h18770474.Hotel-Information) 9.8/10 Exceptional (65) "Location, location, location. The room was great. The host was easy to communicate with and was very helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) peter m. [](https://www.expedia.ca/Montepulciano-Hotels-Charming-House-In-The-Heart-Of-Montepulciano.h18770474.Hotel-Information) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/95000000/94660000/94658800/94658769/bd0cc9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/95000000/94660000/94658800/94658769/93d53faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94660000/94658800/94658769/260b2278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94660000/94658800/94658769/bc12e146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montepulciano [](https://www.expedia.ca/Montepulciano-Hotels-A-MAGICAL-HOLIDAY-IN-TUSCANY.h94658769.Hotel-Information) 9.8/10 Exceptional (8) "Absolutely loved this property. It’s in a great location and has so much character. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy C. [](https://www.expedia.ca/Montepulciano-Hotels-A-MAGICAL-HOLIDAY-IN-TUSCANY.h94658769.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33600000/33597700/33597663/2a4f74c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33600000/33597700/33597663/w2848h4255x0y17-55e549e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33600000/33597700/33597663/97bcf512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/34000000/33600000/33597700/33597663/149fc750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Montepulciano (SI) [](https://www.expedia.ca/Montepulciano-Hotels-LA-CASINA-CANTINI-Panoramic-Apartment-In-Montepulciano-In-The-Historic-Center.h33597663.Hotel-Information) 9.6/10 Exceptional (53) "This was an ideal little find, centrally located across from the Fortezza and behind the historic town center. The space was perfect for a two-person stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynne S. [](https://www.expedia.ca/Montepulciano-Hotels-LA-CASINA-CANTINI-Panoramic-Apartment-In-Montepulciano-In-The-Historic-Center.h33597663.Hotel-Information) ![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/2d2d56ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in Pienza [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) 9.4/10 Exceptional (134) "Such friendly staff, loved Pienza and the property was such a good location! " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Bethan CA $279 CA $316 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/a6535507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/cd3bbebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/38f51959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in Trequanda [](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) 8.8/10 Excellent (166) "Room was beyond expectations. Helpful staff and overall great experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $94 CA $109 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/19000000/18790000/18782100/18782015/3ffb442f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18790000/18782100/18782015/583834ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18790000/18782100/18782015/234c360a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18790000/18782100/18782015/99d48457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Ristonchia [](https://www.expedia.ca/Castiglion-Fiorentino-Hotels-Farmhouse-In-The-Hills-With-Panoramic-View-And-Swimming-Pool.h18782015.Hotel-Information) 9.6/10 Exceptional (75) "Was wonderful and beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alana A. [](https://www.expedia.ca/Castiglion-Fiorentino-Hotels-Farmhouse-In-The-Hills-With-Panoramic-View-And-Swimming-Pool.h18782015.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/822e6f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/4581bc1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/2f21d9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/0dd7cc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Siena [](https://www.expedia.ca/Montalcino-Hotels-Private-And-Cozy-Retreat-In-Montalcino-With-Private-Pool-Surrounded-By-Vineyards.h35329902.Hotel-Information) 9.4/10 Exceptional (67) "What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) peter H. [](https://www.expedia.ca/Montalcino-Hotels-Private-And-Cozy-Retreat-In-Montalcino-With-Private-Pool-Surrounded-By-Vineyards.h35329902.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7dd03bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/b1604ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7a16fc61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, Terrace, Valley View](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/2f810565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence in San Quirico d'Orcia [](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information) 9.0/10 Wonderful (78) "Fantastic place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clifford CA $317 CA $356 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/6a82a5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/cc976759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Sinalunga [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) 10/10 Exceptional (59) "Amazing property! Could not recommend more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annika P. CA $196 CA $229 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/7dffae86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/ce0b1bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/8205fa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/660dd65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in chiusi [](https://www.expedia.ca/Chiusi-Hotels-PRIVATE-TUSCAN-VILLA-WITH-HEATED-SWIMMING-POOL-JACUZZI-SPA-SAUNA-EVENTS.h18764107.Hotel-Information) 10/10 Exceptional (57) "We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Florian Maria W. [](https://www.expedia.ca/Chiusi-Hotels-PRIVATE-TUSCAN-VILLA-WITH-HEATED-SWIMMING-POOL-JACUZZI-SPA-SAUNA-EVENTS.h18764107.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8def11f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8e2d77d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/7d70a4e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/5d163297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montalcino (SI) [](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information) 9.8/10 Exceptional (67) "Really enjoyed our stay. Loved the town and the accommodation was superb. " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Michelle C. CA $243 CA $328 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/e5c35199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/4108e65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/049b00fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/b43cefc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montisi [](https://www.expedia.ca/Montalcino-Hotels-Hilltop-House-In-The-Heart-Of-Tuscany-With-Private-Pool.h34024116.Hotel-Information) 9.8/10 Exceptional (94) "Lovely home with spectacular views! The home greatly exceeded our expectations. It had everything we needed for our 6 day. When not our touring the charming small Tuscany towns, we enjoyed the peace and quiet of the back porch and pool area. We kept the windows open and enjoyed the sweet breezes blowing through. If you're looking the perfect home to rent in Tuscany, this is the one. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa G. [](https://www.expedia.ca/Montalcino-Hotels-Hilltop-House-In-The-Heart-Of-Tuscany-With-Private-Pool.h34024116.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/b96fbe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/691c226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/c550d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/9980acef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montalcino [](https://www.expedia.ca/Montalcino-Hotels-Villa-In-Montalcino.h90300061.Hotel-Information) 10/10 Exceptional (86) "Lovely villa in a beautiful location. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) helen S. [](https://www.expedia.ca/Montalcino-Hotels-Villa-In-Montalcino.h90300061.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29®ionId=601351&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMontepulciano-Vacation-Rentals.d601351.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMontepulciano-Vacation-Rentals.d601351.Travel-Guide-VacationRentals) ## Top Montepulciano Hotel Reviews ![Agriturismo Merigge Wellness & Spa](https://images.trvl-media.com/lodging/41000000/40030000/40021900/40021883/3652c4a4_y.jpg) ### Agriturismo Merigge Wellness & Spa 10/10 Excellent "Friendly staff and super accommodating. We would highly recommend staying there!!!" [](https://expedia.ca/Montepulciano-Hotels-Merigge.h40021883.Hotel-Information) ![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc_y.jpg) ### Relais Villa Grazianella - UNA Esperienze 10/10 Excellent "Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!" [](https://expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Bellarmino Boutique Apartments](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/18007833_y.jpg) ### Bellarmino Boutique Apartments 6/10 Okay "Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!" [](https://expedia.ca/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) ![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg) ### Albergo San Biagio 10/10 Excellent "gorgeous spot below the town, what an incredible view from the balcony " [](https://expedia.ca/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information) ![Villa Svetoni Wine Resort](https://images.trvl-media.com/lodging/101000000/100990000/100989800/100989748/576cc1e4_y.jpg) ### Villa Svetoni Wine Resort 10/10 Excellent "What a wonderful villa wine resort in Tuscany. Great restaurant Michelin star attached and easy access . Staff was very attentive and available at Al times. 10 min drive to Montepulciano " [](https://expedia.ca/Montepulciano-Hotels-Villa-Svetoni-Wine-Resort.h100989748.Hotel-Information) ![Podere La Rocca](https://images.trvl-media.com/lodging/6000000/5140000/5136800/5136719/26ddd5ee_y.jpg) ### Podere La Rocca 10/10 Excellent "Awesome.place to be and Antonio is a star at the restaurant." [](https://expedia.ca/Montepulciano-Hotels-Podere-La-Rocca.h5136719.Hotel-Information) ![Hotel I Due Cigni](https://images.trvl-media.com/lodging/2000000/1260000/1250300/1250287/34bbee35_y.jpg) ### Hotel I Due Cigni 10/10 Excellent "Love, love, loved this hotel. Perfect location, superb breakfast, absolutely wonderful family run hotel! I highly recommend staying at this hotel and visiting the area. Easy to get around with a car or utilizing the bus system. Definitely will stay here again. Thank you, Simonetta, Mateo, Anna and the dad for a wonderful stay." [](https://expedia.ca/Montepulciano-Hotels-Hotel-I-Due-Cigni.h1250287.Hotel-Information) ![Meublé Il Riccio](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/cabc4072_y.jpg) ### Meublé Il Riccio 10/10 Excellent "Staff is great and many good restaurants in short walking distance." [](https://expedia.ca/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information) ![Hotel La Terrazza di Montepulciano](https://images.trvl-media.com/lodging/4000000/3810000/3801900/3801871/2cd509e0_y.jpg) ### Hotel La Terrazza di Montepulciano 10/10 Excellent "Perfect location - could walk everywhere. Roberto and his wife were incredible hosts. They treated us like family. They served us a delicious breakfast, gave us information about restaurants and wine tastings, provided help with transportation. We hope to return soon. This place is a gem. The hosts make it very special. " [](https://expedia.ca/Montepulciano-Hotels-Hotel-La-Terrazza-Di-Montepulciano.h3801871.Hotel-Information) ## Find out more about Montepulciano You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montepulciano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Montepulciano ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Apartments in Montepulciano ](https://expedia.ca/Montepulciano-Apartments.d601351-aaApartments.Travel-Guide-Accommodation) - [Villas in Montepulciano ](https://expedia.ca/Montepulciano-Villas.d601351-aaVillas.Travel-Guide-Accommodation) - [Farmstay in Montepulciano ](https://expedia.ca/Montepulciano-Agritourism.d601351-aaAgritourism.Travel-Guide-Accommodation) - [Vacation Homes in Montepulciano ](https://expedia.ca/Montepulciano-Private-Vacation-Homes.d601351-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Guest Houses in Montepulciano ](https://expedia.ca/Montepulciano-Guest-Houses.d601351-aaGuestHouses.Travel-Guide-Accommodation) - [Townhomes in Montepulciano ](https://expedia.ca/Montepulciano-Townhomes.d601351-aaTownhomes.Travel-Guide-Accommodation) - [B&B in Montepulciano ](https://expedia.ca/Montepulciano-Bed-And-Breakfast.d601351-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Residences in Montepulciano ](https://expedia.ca/Montepulciano-Residences.d601351-aaResidences.Travel-Guide-Accommodation) - [Cottages in Montepulciano ](https://expedia.ca/Montepulciano-Cottages.d601351-aaCottages.Travel-Guide-Accommodation) - [Country Houses in Montepulciano ](https://expedia.ca/Montepulciano-Country-House.d601351-aaCountryHouse.Travel-Guide-Accommodation) - [Chalets in Montepulciano ](https://expedia.ca/Montepulciano-Chalets.d601351-aaChalets.Travel-Guide-Accommodation) - [Resorts in Montepulciano ](https://expedia.ca/Montepulciano-Resort-Hotels.d601351-aaResortHotels.Travel-Guide-Accommodation) - [Condo Rentals in Montepulciano ](https://expedia.ca/Montepulciano-Condos.d601351-aaCondos.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Montepulciano? 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