Cottage vacation rentals 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osceola County cottage rentals
Cottage rentals with a hot tub
Cottage in Kissimmee
4.77 out of 5 average rating, 115 reviews"Beautiful Resort Cottage Near All Attractions!!"
May 24 – 31
Cottage in Kissimmee
4.98 out of 5 average rating, 53 reviewsCozy Orlando Area Cottage - 4 Miles to Disney
Nov 18 – 25
Cottage in Kissimmee
4.98 out of 5 average rating, 58 reviewsGetaway Cottage Near Disney
Apr 20 – 27
Cottage in Kissimmee
4.94 out of 5 average rating, 50 reviewsBeautiful Cottage 1 Bedroom
Sep 9 – 16
Cottage in Kissimmee
4.88 out of 5 average rating, 82 reviewsModern Vacation Cottage near Walt Disney World
Mar 28 – Apr 4
Cottage in Kissimmee
4.87 out of 5 average rating, 54 reviewsCozy Tiny Home Getaway minutes from Disney
Feb 28 – Mar 7
Cottage in Kissimmee
4.82 out of 5 average rating, 76 reviewsSerenity Cottage come relax and enjoy
Dec 16 – 23
Cottage in Kissimmee
4.8 out of 5 average rating, 94 reviewsCozy Cottage 5mins From Disney Parks!
Nov 22 – 29
Pet-friendly cottage rentals
Cottage in Kissimmee
4.87 out of 5 average rating, 153 reviewsLakehouse Cottage - 4 Miles to Disney!
Sep 12 – 19
Cottage in Lake Wales
4.97 out of 5 average rating, 96 reviewsCharming, renovated 1917 Cottage
Aug 6 – 13
Cottage in Davenport
4.98 out of 5 average rating, 58 reviewsClassic Cottage in country setting
Jun 26 – Jul 3
Cottage in River Ranch
4.89 out of 5 average rating, 9 reviewsNEW! River Ranch Cozy Cottage w/ FREE Golf Cart!
Oct 22 – 29
Cottage in Kissimmee
4.82 out of 5 average rating, 33 reviewsDisney Owl Cottage - Kissimmee, Florida
Jun 2 – 9
Cottage in Davenport
4.83 out of 5 average rating, 6 reviewsCharming Cottage #1
Apr 11 – 18
Cottage in Kissimmee
4.73 out of 5 average rating, 37 reviewsBoutique Cottage, in a quiet place close to Parks
Mar 17 – 24
Cottage in Haines City
4.86 out of 5 average rating, 7 reviewsOrlando Area Vacation Home #005
Sep 14 – 21
Private cottage rentals
Cottage in Kissimmee
5.0 out of 5 average rating, 11 reviewsSweet Cottage 4 miles to Disney World
Nov 15 – 22
Cottage in Kissimmee
4.72 out of 5 average rating, 95 reviewsEntire HAPPY HOME @Disney/Universal Parks!!
Sep 11 – 18
Cottage in Kissimmee
4.81 out of 5 average rating, 68 reviewsUpdated Kissimmee Cottage near Disney (5 miles)
Dec 26 – Jan 2
Cottage in Four Corners
4.7 out of 5 average rating, 23 reviews5 Bed Cottage in Margaritaville Close to Parks
Nov 5 – 12
Cottage in Kissimmee
4.83 out of 5 average rating, 115 reviewsTiny house near Disney "Please be our Guest "
Aug 6 – 13
Cottage in Kissimmee
4.74 out of 5 average rating, 133 reviewsSherwood Forest Vacation Home Near Disney
Jun 3 – 10
Cottage in Kissimmee
4.74 out of 5 average rating, 277 reviewsCute Sandcastle Cottage near Disney
Sep 13 – 20
Cottage in Kissimmee
4.95 out of 5 average rating, 38 reviewsMickey's Hideaway Cottage
Jun 3 – 10
Destinations to explore
- Cottage rentals Orlando
- Cottage rentals Florida
- Cottage rentals Florida
- Cottage rentals Kissimmee
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