Cottage accommodation in Osceola County
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Top-rated cottage rentals in Osceola County
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Osceola County cottage rentals
Cottage rentals with a hot tub
Cottage in Kissimmee
4.98 out of 5 average rating, 52 reviewsCozy Orlando Area Cottage - 4 Miles to Disney
18 – 25 Oct
Cottage in Kissimmee
4.98 out of 5 average rating, 57 reviewsGetaway Cottage Near Disney
18 – 25 Aug
Cottage in Kissimmee
4.94 out of 5 average rating, 50 reviewsBeautiful Cottage 1 Bedroom
1 – 8 Apr
Cottage in Kissimmee
4.87 out of 5 average rating, 54 reviewsCozy Tiny Home Getaway minutes from Disney
15 – 22 Feb
Cottage in Kissimmee
4.9 out of 5 average rating, 81 reviewsModern Vacation Cottage near Walt Disney World
30 Nov – 7 Dec
Cottage in Kissimmee
4.82 out of 5 average rating, 76 reviewsSerenity Cottage come relax and enjoy
22 – 29 Jan
Cottage in Kissimmee
4.8 out of 5 average rating, 93 reviewsCozy Cottage 5mins From Disney Parks!
15 – 22 Dec
Cottage in Kissimmee
4.95 out of 5 average rating, 22 reviewsLa Casita - Centrally located
19 – 26 Sept
Pet-friendly cottage rentals
Cottage in Lake Wales
4.97 out of 5 average rating, 94 reviewsCharming, renovated 1917 Cottage
1 – 8 Nov
Cottage in Davenport
4.98 out of 5 average rating, 57 reviewsClassic Cottage in country setting
22 – 29 Sept
Cottage in Kissimmee
4.82 out of 5 average rating, 33 reviewsDisney Owl Cottage - Kissimmee, Florida
18 – 25 Mar
Cottage in River Ranch
4.88 out of 5 average rating, 8 reviewsNEW! River Ranch Cozy Cottage w/ FREE Golf Cart!
21 – 28 June
Cottage in Davenport
4.83 out of 5 average rating, 6 reviewsCharming Cottage #1
4 – 11 Nov
Cottage in Kissimmee
4.69 out of 5 average rating, 42 reviewsChic Cottage near Disney - Lots of Amenities!
10 – 17 Jan
Cottage in St. Cloud
4.75 out of 5 average rating, 4 reviewsCozy Farmhouse near Disney
8 – 15 July
Cottage in Kissimmee
4.8 out of 5 average rating, 5 reviewsKissimmee Cottage w/ Resort-Style Amenities!
7 – 14 Sept
Private cottage rentals
Cottage in Kissimmee
4.86 out of 5 average rating, 391 reviewsYay! Cool Tiny Home Near All the Parks (98)
21 – 28 Mar
Cottage in Lake Wales
4.81 out of 5 average rating, 37 reviewsSuite Retreat by lake & orange groves
29 June – 6 July
Cottage in Kissimmee
5.0 out of 5 average rating, 11 reviewsSweet Cottage 4 miles to Disney World
10 – 17 Nov
Cottage in Kissimmee
4.71 out of 5 average rating, 94 reviewsEntire HAPPY HOME @Disney/Universal Parks!!
28 July – 4 Aug
Cottage in Kissimmee
4.81 out of 5 average rating, 68 reviewsUpdated Kissimmee Cottage near Disney (5 miles)
13 – 20 July
Cottage in Four Corners
4.7 out of 5 average rating, 23 reviews5 Bed Cottage in Margaritaville Close to Parks
21 – 28 Sept
Cottage in Kissimmee
4.82 out of 5 average rating, 114 reviewsTiny house near Disney "Please be our Guest "
10 – 17 Aug
Cottage in Kissimmee
4.74 out of 5 average rating, 133 reviewsSherwood Forest Vacation Home Near Disney
6 – 13 June
Destinations to explore
- Cottage rentals Orlando
- Cottage rentals Florida
- Cottage rentals Florida
- Cottage rentals Kissimmee
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