Osceola Holiday Rentals

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Check prices for these dates

Tonight
17 Jul - 18 Jul
Tomorrow
18 Jul - 19 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Osceola

Beautiful Waterfront Home on Baugo Bay
Exterior

Beautiful Waterfront Home on Baugo Bay

9.6 out of 10, Exceptional, (29)
"Gregg's home was very neat, clean and had everything you could need. The view was beautiful. Thank you for a great stay."
The price is HK$3,925
HK$5,154 total
includes taxes & fees
11 Aug - 12 Aug
Beautiful Waterfront Home on Baugo Bay
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Exterior

Charming 3-bedroom house located on Main Street in Downtown Middlebury

Charming 3-bedroom house located on Main Street in Downtown Middlebury
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Outdoor spa tub

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (54)
"Overall a good place to stay in the area."
The price is HK$903
HK$1,900 total
includes taxes & fees
24 Jul - 25 Jul
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
The Loft 3BR Apartment with Scenic Deck
Fridge, microwave, oven, coffee/tea maker

The Loft 3BR Apartment with Scenic Deck

6.0 out of 10, (1)
"Okay, we came after it had snow a few days prior and nothing was cleared on the many steps nor ramp path, so 6 of us trudged thru snow then tracked snow up wooden stairs that really need some type of padding. NOT for elderly or anyone with steps problems.The 3 beds were so uncomfortable, squeaky and thin; I was able to can feel the mattress quilting through the sheets.The decorative pillow in my bedroom, smelled happily of someone’s cologne.Not impressed at all. Not terrible, but no screens in...
The price is HK$1,177
HK$3,426 total
includes taxes & fees
13 Aug - 14 Aug
The Loft 3BR Apartment with Scenic Deck
Rock Run Creek House
Dining

Rock Run Creek House

The price is HK$3,281
HK$4,899 total
includes taxes & fees
29 Jul - 30 Jul
Rock Run Creek House
Hilltop Family Retreat
Fridge, microwave, oven, dishwasher

Hilltop Family Retreat

10.0 out of 10, Exceptional, (1)
"Property appears to be recently remodeled and up to date with plenty of space for large groups. 3 bathrooms so no one has to wait. Upstairs can be warm during the summer but nothing a fan doesn't fix. Property owner is responsive and easy to reach."
The price is HK$3,238
HK$4,817 total
includes taxes & fees
21 Jul - 22 Jul
Hilltop Family Retreat
Beautiful Private Setting !!!
Exterior

Beautiful Private Setting !!!

9.8 out of 10, Exceptional, (20)
"Well kept and clean"
The price is HK$1,688
HK$3,226 total
includes taxes & fees
20 Jul - 21 Jul
Beautiful Private Setting !!!
Riverhaven! Gorgeous A-Frame On St Joe River!!
Dining

Riverhaven! Gorgeous A-Frame On St Joe River!!

10.0 out of 10, Exceptional, (21)
"Everything was incredible and owner was very responsive. We will definitely stay there again."
The price is HK$4,239
HK$6,996 total
includes taxes & fees
29 Jul - 30 Jul
Riverhaven! Gorgeous A-Frame On St Joe River!!
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Outdoor pool

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (25)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is HK$2,649
HK$4,901 total
includes taxes & fees
23 Jul - 24 Jul
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
Outdoor spa tub

Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa

8.0 out of 10, Very good, (1)
"We came here with 8 people, four young kids, we had fun in the hot tub and the sleeping arraignments were great, beds were comfortable enough and the kids loved the swim spa, and the view is super cool, watching birds and wild life in the river. We would recommend this place even in the winter. "
The price is HK$3,218
HK$5,661 total
includes taxes & fees
4 Aug - 5 Aug
Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
Lakeshore Cottage
Fridge, microwave, oven, stovetop

Lakeshore Cottage

9.8 out of 10, Exceptional, (16)
"Our family of 5 loved our stay here. The lake property was so quiet and clean. We loved the house layout and enjoyed the kayaks so much! It was perfect for our family!"
The price is HK$2,889
HK$4,662 total
includes taxes & fees
23 Jul - 24 Jul
Lakeshore Cottage
Couples Hideaway, Romantic, Private, Shipshewana close, Nature, Trails, Wildlife
Terrace/patio

Couples Hideaway, Romantic, Private, Shipshewana close, Nature, Trails, Wildlife

10.0 out of 10, Exceptional, (25)
"We loved our stay at this place! It was very clean and the host thought of everything!"
The price is HK$883
HK$1,509 total
includes taxes & fees
21 Jul - 22 Jul
Couples Hideaway, Romantic, Private, Shipshewana close, Nature, Trails, Wildlife
The Gemini
Private kitchen

The Gemini

9.6 out of 10, Exceptional, (7)
"We have friends that live close. This was the perfect location for a weekend visit."
The price is HK$1,013
HK$1,251 total
includes taxes & fees
1 Aug - 2 Aug
The Gemini
Simonton Lake house with Pontoon, Kayaks, Ping Pong, Fire Pit, + Outdoor Darts
Property grounds

Simonton Lake house with Pontoon, Kayaks, Ping Pong, Fire Pit, + Outdoor Darts

Simonton Lake house with Pontoon, Kayaks, Ping Pong, Fire Pit, + Outdoor Darts
Woodside Retreat in the Heart of Amish Country
Dining

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (5)
"We had a wonderful time here. We stayed here to "unplug" and refresh and it was the perfect place to do so! Comfortable, very clean, with personal touches down to the snacks provided- all made for a stay we will be back for!"
The price is HK$903
HK$1,587 total
includes taxes & fees
18 Jul - 19 Jul
Woodside Retreat in the Heart of Amish Country
Restored historic home near ND and Amish Country
Exterior detail

Restored historic home near ND and Amish Country

10.0 out of 10, Exceptional, (3)
"Perfect home to stay with tons of room, great layout in a historic home. Plenty of room inside and out. "
The price is HK$1,714
HK$3,404 total
includes taxes & fees
23 Jul - 24 Jul
Restored historic home near ND and Amish Country
3BD/2.5 Home|5m DT Elkhart|30m Notre |River View
Smart TV, fireplace

3BD/2.5 Home|5m DT Elkhart|30m Notre |River View

10.0 out of 10, Exceptional, (2)
"Everything was perfect. So clean and restful for our stay! Would stay again!"
3BD/2.5 Home|5m DT Elkhart|30m Notre |River View
Choo Choo Inn
Property grounds

Choo Choo Inn

10.0 out of 10, Exceptional, (24)
"The Choo Choo Inn was so cozy and comfortable and the host left us a basket of treats waiting for us when we arrived. It was so well appointed with everything we needed and decorated so cute! We’ll definitely look to staying there again when we go back to visit Notre Dame 😊"
The price is HK$1,134
HK$1,753 total
includes taxes & fees
29 Jul - 30 Jul
Choo Choo Inn
Treehouse Acres, Treehouse Acres Vacation Home
Terrace/patio

Treehouse Acres, Treehouse Acres Vacation Home

9.4 out of 10, Exceptional, (3)
"We stayed just one evening for an event occurring at Notre Dame the following day. Other family members are planning a return trip for a weekend."
The price is HK$1,460
HK$2,993 total
includes taxes & fees
11 Aug - 12 Aug
Treehouse Acres, Treehouse Acres Vacation Home
Clean, Kid-Friendly, 12 Min. From Notre Dame
Terrace/patio

Clean, Kid-Friendly, 12 Min. From Notre Dame

10.0 out of 10, Exceptional, (4)
"Kelli was an amazing host! The home was very clean and spacious enough for a large group. I would definitely stay here again — highly recommend!"
The price is HK$4,710
HK$6,192 total
includes taxes & fees
3 Aug - 4 Aug
Clean, Kid-Friendly, 12 Min. From Notre Dame
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.
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Frequently asked questions

Are there holiday rentals in Osceola?

Yes, there are holiday rentals close to the most popular sights in Osceola, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osceola has to offer?

2 Miles from NOTRE DAME, Brand New Spacious House! : This holiday home rental outside of Osceola has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Osceola?

Choose from 7 Expedia holiday rentals in Osceola for a memorable holiday.

What’s there to see and do in Osceola?

Explore the area and family-friendly sights such as Merrifield Ice Rink, or get out into nature at a spot like Merrifield Pool. The Lerner and Midwest Museum of American Art are a couple of places you'll find in the wider area.

What’s a holiday rental in Osceola like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osceola. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.