
Vacation rentals in Osceola
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Top-rated vacation rentals in Osceola
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Osceola vacation rentals
Other great vacation rentals in Osceola
Guest favorite

Home in Berrien Springs
4.95 out of 5 average rating, 123 reviewsGreat Living Too
MichelleRating, 5 stars2 months ago
I cannot say enough about how clean the house was. Wonderful space for everyone. Kitchen table was large enough for my group to play games at and the basement space was large enough for everyone too! If we are back in the area we would stay here again!
Guest favorite

Cottage in Dowagiac
4.9 out of 5 average rating, 49 reviewsStylish Lakehouse, Sandy Beach Includes lux Boat!
StacyRating, 5 stars6 months ago
Kelly was easy to work with, had great communication, was very accommodating, and the cottages were so cozy & quaint! The biggest plus was getting the opportunity to use that amazing pontoon boat and getting out on the lake. We would definitely stay at this lake again! What a fun area. Having such a fun time we started looking at Kelly’s other properties for future getaways!
Superhost

Home in Three Oaks
4.82 out of 5 average rating, 11 reviewsSunny Door Cottage| Downtown| 10 min to beach
JamieRating, 5 stars6 months ago
Cozy spot and super quiet! It has a great "old house" vibe without feeling like it's rickety or weak. Three Oaks is pretty small to even begin the edge of town, it's a very short and pleasant walk to downtown.a Also the bed linens are top notch! We slept great.
Top guest favorite

Home in Three Oaks
5 out of 5 average rating, 33 reviewsPrivate! Cherry Beach Pool House
KyleRating, 5 stars7 months ago
We loved our stay at Cherry Beach. We brought our son and it was very baby friendly. The pool was awesome and the backyard was so big it felt like you were in the wilderness. Mary was really helpful too and we felt right at home. It was a great holiday weekend.
Superhost

Apartment in Warsaw
5 out of 5 average rating, 4 reviewsBarbee Hill 2BR Home, Wi-Fi, Fun
BRENDARating, 5 stars19 months ago
Thanks for hosting! It was awesome 👏 😎
Top guest favorite

Cottage in Union Pier
4.96 out of 5 average rating, 200 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
SarahRating, 5 stars2 weeks ago
Birthday brownies upon arrival! Great quiet location but very convenient for local shops and restaurants. Can walk to the beach! Can’t wait for the opportunity to visit again
Guest favorite

Home in Dowagiac
4.71 out of 5 average rating, 63 reviewsLorlee - A Large and Luxurious Lakefront Cottage!
TerryRating, 5 stars9 months ago
Great home! Perfect for our family really really enjoyed our stay
Guest favorite

Home in Union Pier
4.96 out of 5 average rating, 114 reviewscozy new buffalo cabin, hot tub, 14m walk to beach
TimothyRating, 5 stars4 weeks ago
very fun relaxing experience, stayed in the back cabin. great time
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