Title: Monsigliolo Vacation Rentals from $101: Search Short-Term Rentals | Expedia.com [Monsigliolo Travel Guide](https://expedia.com/Monsigliolo.dx6361279)[Hotels in Monsigliolo](https://expedia.com/Monsigliolo-Hotels.d6361279.Travel-Guide-Hotels)[Flights to Monsigliolo](https://expedia.com/Cheap-Flights-To-Monsigliolo.d6361279.Travel-Guide-Flights)[Car Rentals in Monsigliolo](https://expedia.com/Car-Rentals-In-Monsigliolo.d6361279.Car-Rental-Guide)[Monsigliolo Vacation Packages](https://expedia.com/Monsigliolo.d6361279.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6361279&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6361279&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6361279&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6361279&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Monsigliolo vacation rentals ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99.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) ![Royal Suite, Hot Tub (SPA) | Private spa tub](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/8f72c3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/9c2d8838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Abbadia Sicille Relais [](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) Trequanda 8.8/10 Excellent (168 reviews) "Room was beyond expectations. Helpful staff and overall great experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $88 nightly $101 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Triple Room | Bathroom | Shower, free toiletries, hair dryer, bidet](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c1f8c360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artisti del Cavallo Tourism [](https://www.expedia.com/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information) Foiano della Chiana 8.4/10 Very Good (24 reviews) "Good house for one night. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Heiner $84 nightly $95 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/1def40b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/a1afa9f4.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) ### Residenza Fabroni [](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) Montepulciano 8.8/10 Excellent (96 reviews) "gorgeous historical property, very attentive host, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah $89 nightly $103 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/16000000/15180000/15172000/15171917/d0a1fe71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15180000/15172000/15171917/a101de5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Mobile Home | In-room dining](https://images.trvl-media.com/lodging/16000000/15180000/15172000/15171917/8d1e2ecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/16000000/15180000/15172000/15171917/4714eda6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Badiaccia Camping Village [](https://www.expedia.com/Castiglione-Del-Lago-Hotels-Badiaccia-Camping-Village.h15171917.Hotel-Information) Castiglione del Lago 8.0/10 Very Good (10 reviews) "Very clean, nice location, efficient and courteous staff. Unfortunately, out of the many daily activities advertised on the website, almost none took place, and the mini club was basically just sitting the children down and make them colour/paint. The swimming pool was always very very busy, and because of the heat, the lake level was very low, it was not very inviting, and no canoe or kayaks were available for hire. The internal mini-market is very expensive. All in all it's a nice place, maybe... ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Emanuele $162 nightly $176 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Castiglione-Del-Lago-Hotels-Badiaccia-Camping-Village.h15171917.Hotel-Information) ![Panoramic Cottage, 1 Bedroom | Exterior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/e878f092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/6e2ad2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/a39f2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Affitacamere Maria Gabriella [](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information) Pienza 9.8/10 Exceptional (51 reviews) "This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lenise $134 nightly $152 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/c3f2502a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double or Twin Room, 1 Bedroom | Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/41636195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/b87c70b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/30d81c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### THE MONNA LISA RESORT [](https://www.expedia.com/Arezzo-Hotels-La-Valle-Di-Monna-Lisa.h24373081.Hotel-Information) Arezzo 9.2/10 Wonderful (9 reviews) "Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bart [](https://www.expedia.com/Arezzo-Hotels-La-Valle-Di-Monna-Lisa.h24373081.Hotel-Information) ![Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/f7106947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/cc713796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Monolocale Exclusive, vista città, secondo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/6be6d8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Monolocale Exclusive, vista città, secondo piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/4381c139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TuscanyLettings Studio&Room [](https://www.expedia.com/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information) Pienza 10/10 Exceptional (1 review) "メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。" ![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg) keita $95 nightly $110 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/12000000/11650000/11645900/11645872/d2dd8e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11650000/11645900/11645872/199eaac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/12000000/11650000/11645900/11645872/5cf4b285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/12000000/11650000/11645900/11645872/03afc9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cameracaffè Centro [](https://www.expedia.com/Arezzo-Hotels-Cameracaffe-Centro.h11645872.Hotel-Information) Arezzo Centro Storico 8.6/10 Excellent (180 reviews) "Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith $90 nightly $107 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Arezzo-Hotels-Cameracaffe-Centro.h11645872.Hotel-Information) ![Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/4f1f04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/0f43b292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/8ce91a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Silvio al secondo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/884c0781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PienzaLettings Suites [](https://www.expedia.com/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) Pienza 10/10 Exceptional (2 reviews) "Fantastic room in the city center, close to everything in Pienza" ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Tom $101 nightly $116 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1589x0y0-ab9335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/d953c731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casa Olivieri, vista città, 1 piano senza ascensore | Private kitchen | Fridge, microwave, stovetop, electric kettle](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f32e69c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/5ded1ab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Gioia - Casa Olivieri [](https://www.expedia.com/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information) Pienza $95 nightly $110 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information) ![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5467h3644x6y6-bfae763b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5470h3644x0y0-9c1f6ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/543e1f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/81c3f8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DormiVeglia B&B [](https://www.expedia.com/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information) Monte San Savino 10/10 Exceptional (27 reviews) "Amazing, warm, sweet, lovely, such a gem of a place!" ![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg) Melissa Hyun Joo [](https://www.expedia.com/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/21000000/20250000/20241800/20241795/53534487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/21000000/20250000/20241800/20241795/02e04c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/21000000/20250000/20241800/20241795/fa17805b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/21000000/20250000/20241800/20241795/44d81f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Allegra Toscana - Affittacamere Guest house [](https://www.expedia.com/Arezzo-Hotels-Allegra-Toscana.h20241795.Hotel-Information) Arezzo Centro Storico 7.0/10 Good (16 reviews) "Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Justin $74 nightly $94 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Arezzo-Hotels-Allegra-Toscana.h20241795.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/fbee2bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/cb18eaa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/ba2e3caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/08170cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boutique Apartment Family [](https://www.expedia.com/Chiusi-Hotels-Boutique-Apartment-Family.h110580126.Hotel-Information) Chiusi $82 nightly $100 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Chiusi-Hotels-Boutique-Apartment-Family.h110580126.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/d732a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/9d10099d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Bathroom | Free toiletries, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/8842009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Terrace | Desk, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/93858826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Piccola Locanda [](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information) Chiusi 8.6/10 Excellent (9 reviews) "This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffery [](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/adbd192d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/ee21b4e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/35d33457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/63933730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday home with panoramic terrace ideal for families and couples [](https://www.expedia.com/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.Hotel-Information) Cortona $104 nightly $104 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/c9197a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/c1b69eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/9f410eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/8bdff2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe room Cartazucchero in the heart of Arezzo [](https://www.expedia.com/Arezzo-Hotels-Deluxe-Room-Cartazucchero-In-The-Heart-Of-Arezzo.h109033481.Hotel-Information) Arezzo Centro Storico 10/10 Exceptional (2 reviews) "From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hector $78 nightly $86 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Arezzo-Hotels-Deluxe-Room-Cartazucchero-In-The-Heart-Of-Arezzo.h109033481.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/0c33efbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/f0b51bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/c07b4937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/6349a215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi [](https://www.expedia.com/Pienza-Hotels-Apartment-La-Dimora-Di-Pienza-In-Val-DOrcia-With-Wi-Fi.h124117240.Hotel-Information) Pienza $109 nightly $113 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Apartment-La-Dimora-Di-Pienza-In-Val-DOrcia-With-Wi-Fi.h124117240.Hotel-Information) ![Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets](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 | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/4add3036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/85f0e899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/302bfcfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bellarmino Boutique Apartments [](https://www.expedia.com/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) Montepulciano 6.0/10 (1 review) "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 $89 nightly $102 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119600000/119595800/119595715/d620a5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119595800/119595715/170d5f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119595800/119595715/b7770e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119595800/119595715/4b66fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tolletta 10 e Lode - One Bedroom House, Sleeps 4 [](https://www.expedia.com/Arezzo-Hotels-Tolletta-10-E-Lode-One-Bedroom-House.h119595715.Hotel-Information) Arezzo Centro Storico 10/10 Exceptional (1 review) " La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima " ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Maria Gemma $167 nightly $167 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Arezzo-Hotels-Tolletta-10-E-Lode-One-Bedroom-House.h119595715.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/25737385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/47257042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/8c44b07b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Offices](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/020b6380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dolce Casa 2 Summary: [](https://www.expedia.com/Arezzo-Hotels-Dolce-Casa-2-Summary.h92018366.Hotel-Information) Arezzo $117 nightly $117 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Arezzo-Hotels-Dolce-Casa-2-Summary.h92018366.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.com/Hotel-Search?startDate=2026-03-14&endDate=2026-03-15®ionId=6361279&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_6361279) ## Find vacation rentals that suit your style Villas [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=COTTAGE) Residences [](https://www.expedia.com/Hotel-Search?destination=Monsigliolo%2C+Cortona%2C+Tuscany%2C+Italy®ionId=6361279&latLong=43.246256%2C11.944275&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=RESIDENCE) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMonsigliolo-Vacation-Rentals.d6361279.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMonsigliolo-Vacation-Rentals.d6361279.Travel-Guide-VacationRentals) ## Top Monsigliolo Hotel Reviews ![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg) ### Albergo San Biagio 10/10 Excellent "Muy amable " [](https://expedia.com/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information) ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg) ### Monastero di Cortona Hotel & Spa 10/10 Excellent "Everything was great! Lovely hotel " [](https://expedia.com/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "A little tired, extremely clean, with an amazing staff" [](https://expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Hotel Continentale](https://images.trvl-media.com/lodging/2000000/1750000/1749400/1749370/73e76ee4_y.jpg) ### Hotel Continentale 10/10 Excellent "Great location and nice staff " [](https://expedia.com/Arezzo-Hotels-Hotel-Continentale.h1749370.Hotel-Information) ![Grand Hotel Terme](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289175/3fd53b10_y.jpg) ### Grand Hotel Terme 10/10 Excellent "Clean room and friendly staff" [](https://expedia.com/Chianciano-Terme-Hotels-Grand-Hotel-Terme.h1289175.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.com/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Borgo Sant'Ambrogio Resort](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/bd574044_y.jpg) ### Borgo Sant'Ambrogio Resort 10/10 Excellent "It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!" [](https://expedia.com/Trequanda-Hotels-Borgo-SantAmbrogio-Resort.h24046952.Hotel-Information) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Wonderful stay. Very welcoming staff and check in was quick and simple. Very convenient as parking provided. Room was spacious especially bathroom with great bathtub Breakfast was perfect" [](https://expedia.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Lupaia](https://images.trvl-media.com/lodging/2000000/1930000/1923100/1923032/f0f5b944_y.jpg) ### Lupaia 10/10 Excellent "I absolutely loved my stay. The room was comfortable, the food was amazing, and the staff were incredibly kind and helpful. This was my second visit, and I’m already planning to come back again. Some of my best memories of Italy were made here. thank you for another wonderful experie" [](https://expedia.com/Torrita-Di-Siena-Hotels-Lupaia.h1923032.Hotel-Information) ## Find out more about Monsigliolo **Everything you need to know about Monsigliolo vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monsigliolo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monsigliolo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Monsigliolo vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Monsigliolo. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monsigliolo in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Monsigliolo rentals** At Expedia, we put the best Monsigliolo vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Monsigliolo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monsigliolo vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monsigliolo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) ## Frequently asked questions ### Can I find a vacation rental in Monsigliolo? ### What are some of the best vacation rentals in Monsigliolo? ### How many vacation rentals are there in Monsigliolo? ### What’s there to see and do in Monsigliolo? ### What’s a vacation rental in Monsigliolo like? ### Expedia's Latest Trends Hotels - [Hotel Rooms in Porto Ercole](https://expedia.com/Porto-Ercole-Hotels.d11392.Travel-Guide-Hotels) - [San Vivaldo Gay friendly Hotels](https://expedia.com/San-Vivaldo-Hotels-LGBT-Welcoming-Hotel.0-0-d6359598-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels) Cars - [Hertz Car Rentals In Porto Ercole](https://expedia.com/Hertz-Car-Rentals-In-Porto-Ercole.d11392-c40.Car-Rental-Guide-Suppliers) - [Hertz Car Rentals In Terontola](https://expedia.com/Hertz-Car-Rentals-In-Terontola.d6025579-c40.Car-Rental-Guide-Suppliers) Activities - [Things to do in Camucia](https://expedia.com/Things-To-Do-In-Camucia.d6289367.Travel-Guide-Activities) - [Things to do in Saturnia](https://expedia.com/Things-To-Do-In-Saturnia.d4325.Travel-Guide-Activities) - [Things to do in Porto Ercole](https://expedia.com/Things-To-Do-In-Porto-Ercole.d11392.Travel-Guide-Activities) - [Things to do in Montisi](https://expedia.com/Things-To-Do-In-Montisi.d3000027304.Travel-Guide-Activities) - [Things to do in Marina di Carrara](https://expedia.com/Things-To-Do-In-Marina-Di-Carrara.d6292496.Travel-Guide-Activities) - [Things to do in Porto Santo Stefano](https://expedia.com/Things-To-Do-In-Porto-Santo-Stefano.d6025634.Travel-Guide-Activities) - [Things to do in Marina di Pisa](https://expedia.com/Things-To-Do-In-Marina-Di-Pisa.d6059573.Travel-Guide-Activities) Packages - [Pergo Packages](https://expedia.com/Pergo.d6342993.Destination-Travel-Guides) General - [Visit Tirrenia](https://expedia.com/Tirrenia.dx6054392) - [Visit Porto Ercole](https://expedia.com/Porto-Ercole.dx11392) - [Visit Acquaviva](https://expedia.com/Acquaviva.dx6047638) - [Visit Cignano](https://expedia.com/Cignano.dx6361206) - [Visit Albinia](https://expedia.com/Albinia.dx6342096) - [Visit Casorbica-Salcotto](https://expedia.com/Casorbica-Salcotto.dx6361288) - [Visit Porto Santo Stefano](https://expedia.com/Porto-Santo-Stefano.dx6025634) - [Visit Terontola](https://expedia.com/Terontola.dx6025579) - [Visit Lungarno del Tempio](https://expedia.com/Lungarno-Del-Tempio.dx6141944) - [Visit Panzano in Chianti](https://expedia.com/Panzano-In-Chianti.dx602564) - [Visit Le Rocchette](https://expedia.com/Le-Rocchette.dx6292830) - [Visit Vorno](https://expedia.com/Vorno.dx6130888) - [Visit Marina di Pietrasanta](https://expedia.com/Marina-Di-Pietrasanta.dx6034925) - [Visit Montecatini Alto](https://expedia.com/Montecatini-Alto.dx6047856) - [Visit San Donato in Poggio](https://expedia.com/San-Donato-In-Poggio.dx6292835) - [Visit Marina di Grosseto](https://expedia.com/Marina-Di-Grosseto.dx6292498) - [Visit Marina di Massa](https://expedia.com/Marina-Di-Massa.dx6049328) - [Visit Arcetri](https://expedia.com/Arcetri.dx6142058) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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