Title: Ossaia Vacation Rentals from $94: Search Short-Term Rentals | Expedia.com

[Ossaia Travel Guide](https://expedia.com/Ossaia.dx6361235)[Hotels in Ossaia](https://expedia.com/Ossaia-Hotels.d6361235.Travel-Guide-Hotels)[Flights to Ossaia](https://expedia.com/Cheap-Flights-To-Ossaia.d6361235.Travel-Guide-Flights)[Car Rentals in Ossaia](https://expedia.com/Car-Rentals-In-Ossaia.d6361235.Car-Rental-Guide)[Ossaia Vacation Packages](https://expedia.com/Ossaia.d6361235.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=6361235&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=6361235&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=6361235&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=6361235&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 Ossaia vacation rentals

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/f0bca152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa | Living area | 24-inch flat-screen TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/58622732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/08c45c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/5c9c109c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in Trequanda

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.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)

![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/6e2ad2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Cottage, 1 Bedroom | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/83ad69a9.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)

### Townhouse in Pienza

[](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

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 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/e34058f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/304acfc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/e7d80660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/6f9d8ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in La Valle

[](https://www.expedia.com/Magione-Hotels-Villa-Graziella.h86163088.Hotel-Information)

9.6/10

Exceptional

(8 reviews)

"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cinzia c.

$195 nightly

$195 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Magione-Hotels-Villa-Graziella.h86163088.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 Double Bed | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/274ea02b.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)

![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)

### Residence in Trequanda

[](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

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

$89 nightly

$102 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/9d10099d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Chiusi

[](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

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

$121 nightly

$136 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.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)

![Gazebo](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c1f8c360.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)

### Villa in Foiano della Chiana

[](https://www.expedia.com/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

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 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/0d27663a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room | Premium bedding, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/d191efd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, Jetted Tub | Deep soaking bathtub](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/188597d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![22-inch TV with digital channels](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/5ed68d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Montepulciano

[](https://www.expedia.com/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

9.6/10

Exceptional

(128 reviews)

"Great hosts, central location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander

$100 nightly

$114 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100690000/100684600/100684575/62c9a2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100690000/100684600/100684575/83b03268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double or Twin Room | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100690000/100684600/100684575/3cf9a8b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/101000000/100690000/100684600/100684575/83a8da1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Corciano

[](https://www.expedia.com/Corciano-Hotels-L-Antica-Sosta.h100684575.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"Molto accoglienti e gentili "

![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg)

Valentina

$63 nightly

$69 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Corciano-Hotels-L-Antica-Sosta.h100684575.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0263d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/f4cb97cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/26e5f82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/bfee31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Montepulciano

[](https://www.expedia.com/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

9.8/10

Exceptional

(133 reviews)

"Spotless, clean. Staff were friendly. Location and view was spectacular"

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Kim

$155 nightly

$176 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.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)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/12afb28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Montepulciano

[](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

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

$83 nightly

$96 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.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)

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119600000/119595800/119595715/3e892bbc.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)

### Vacation Home in Arezzo Centro Storico

[](https://www.expedia.com/Arezzo-Hotels-Tolletta-10-E-Lode-One-Bedroom-House.h119595715.Hotel-Information)

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 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Arezzo-Hotels-Tolletta-10-E-Lode-One-Bedroom-House.h119595715.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/7998cd17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/bfe877c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/905084fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/f6f7b43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in CHIANCIANO

[](https://www.expedia.com/Chianciano-Terme-Hotels-MONTEPULCIANO-A-DUE-PASSI-DALLA-VAL-DORCIA.h84515383.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rob C.

$403 nightly

$403 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Chianciano-Terme-Hotels-MONTEPULCIANO-A-DUE-PASSI-DALLA-VAL-DORCIA.h84515383.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)

![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/63933730.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)

### Vacation Home in Cortona

[](https://www.expedia.com/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.Hotel-Information)

$104 nightly

$104 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.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)

![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/936c2188.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)

### Townhouse in Monte San Savino

[](https://www.expedia.com/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information)

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)

![Interior](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/fbee2bb8.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)

![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)

![Shower, hair dryer](https://images.trvl-media.com/lodging/111000000/110590000/110580200/110580126/40e1855a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Chiusi

[](https://www.expedia.com/Chiusi-Hotels-Boutique-Apartment-Family.h110580126.Hotel-Information)

$88 nightly

$108 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Chiusi-Hotels-Boutique-Apartment-Family.h110580126.Hotel-Information)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/6e91d9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/824ca8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/49bf4281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/5d93306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monticchiello

[](https://www.expedia.com/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

10/10

Exceptional

(8 reviews)

"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Dan

$139 nightly

$144 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/0aaa13a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/8011dd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/45d9565e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/cabc4072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Montepulciano

[](https://www.expedia.com/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

9.8/10

Exceptional

(88 reviews)

"Staff is great and many good restaurants in short walking distance."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mark

$168 nightly

$189 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

![Suite Aria | Terrace/patio](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/17c800cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/4522b02a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite Marcello | Premium bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/f6347dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/7ee71db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Montepulciano

[](https://www.expedia.com/Montepulciano-Hotels-Delcorto-Suites.h95240092.Hotel-Information)

10/10

Exceptional

(34 reviews)

"Wonderful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rocio Q

$181 nightly

$204 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Delcorto-Suites.h95240092.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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/d344d3b5.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)

![Interior](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033481/8bdff2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Arezzo Centro Storico

[](https://www.expedia.com/Arezzo-Hotels-Deluxe-Room-Cartazucchero-In-The-Heart-Of-Arezzo.h109033481.Hotel-Information)

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

$85 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Arezzo-Hotels-Deluxe-Room-Cartazucchero-In-The-Heart-Of-Arezzo.h109033481.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2239000/2238963/0eb51ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2239000/2238963/9566823b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/3000000/2240000/2239000/2238963/29f6f2a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite | Bathroom | Shower, free toiletries, hair dryer, bidet](https://images.trvl-media.com/lodging/3000000/2240000/2239000/2238963/8176edca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Chiusi

[](https://www.expedia.com/Chiusi-Hotels-Borgo-Dolciano.h2238963.Hotel-Information)

9.0/10

Wonderful

(25 reviews)

"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Carla

$140 nightly

$157 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Chiusi-Hotels-Borgo-Dolciano.h2238963.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=2026-03-12&endDate=2026-03-13&regionId=6361235&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_6361235)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CONDO)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Ossaia%2C+Cortona%2C+Tuscany%2C+Italy&regionId=6361235&latLong=43.233791%2C12.003516&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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%2FOssaia-Vacation-Rentals.d6361235.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssaia-Vacation-Rentals.d6361235.Travel-Guide-VacationRentals)

## Top Ossaia 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 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)

![Best Western Hotel Quattrotorri Perugia](https://images.trvl-media.com/lodging/2000000/1330000/1321400/1321350/d25dd609_y.jpg)

### Best Western Hotel Quattrotorri Perugia

10/10 Excellent

"Everything perfect!"

[](https://expedia.com/Perugia-Hotels-Best-Western-Hotel-Quattrotorri-Perugia.h1321350.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)

![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)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg)

### Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "

[](https://expedia.com/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information)

## Find out more about Ossaia

**Everything you need to know about Ossaia 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 Ossaia 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 Ossaia vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Ossaia vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Ossaia. 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 Ossaia 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 $94 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 Ossaia rentals**

At Expedia, we put the best Ossaia 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 Ossaia 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 Ossaia 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 Ossaia. 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

### Are there vacation rentals in Ossaia?

### What are some of the best vacation home rentals in Ossaia?

### How many vacation rentals are there in Ossaia?

### What’s there to see and do in Ossaia?

### What’s a vacation rental in Ossaia like?

![](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.

Scan the QR code with your device camera and download our app