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!!"
Sep 15 – 22
Cottage in Kissimmee
4.98 out of 5 average rating, 58 reviewsGetaway Cottage Near Disney
Mar 25 – Apr 1
Cottage in Kissimmee
4.94 out of 5 average rating, 50 reviewsBeautiful Cottage 1 Bedroom
Sep 9 – 16
Cottage in Kissimmee
4.98 out of 5 average rating, 53 reviewsCozy Orlando Area Cottage - 4 Miles to Disney
Nov 17 – 24
Cottage in Kissimmee
4.87 out of 5 average rating, 54 reviewsCozy Tiny Home Getaway minutes from Disney
Feb 26 – Mar 5
Cottage in Kissimmee
4.88 out of 5 average rating, 82 reviewsModern Vacation Cottage near Walt Disney World
Jul 14 – 21
Cottage in Kissimmee
4.82 out of 5 average rating, 76 reviewsSerenity Cottage come relax and enjoy
Dec 17 – 24
Cottage in Kissimmee
4.8 out of 5 average rating, 94 reviewsCozy Cottage 5mins From Disney Parks!
Oct 28 – Nov 4
Pet-friendly cottage rentals
Cottage in Kissimmee
4.87 out of 5 average rating, 154 reviewsLakehouse Cottage - 4 Miles to Disney!
Feb 1 – 8
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
Oct 21 – 28
Cottage in River Ranch
4.89 out of 5 average rating, 9 reviewsNEW! River Ranch Cozy Cottage w/ FREE Golf Cart!
Oct 24 – 31
Cottage in Kissimmee
4.82 out of 5 average rating, 33 reviewsDisney Owl Cottage - Kissimmee, Florida
Apr 21 – 28
Cottage in Davenport
4.83 out of 5 average rating, 6 reviewsCharming Cottage #1
Nov 23 – 30
Cottage in Kissimmee
4.73 out of 5 average rating, 37 reviewsBoutique Cottage, in a quiet place close to Parks
Dec 5 – 12
Cottage in Kissimmee
4.86 out of 5 average rating, 14 reviewsMagic in Margaritaville! New, Modern Condo for 7
Aug 11 – 18
Private cottage rentals
Cottage in Kissimmee
5.0 out of 5 average rating, 11 reviewsSweet Cottage 4 miles to Disney World
Aug 20 – 27
Cottage in Kissimmee
4.72 out of 5 average rating, 96 reviewsEntire HAPPY HOME @Disney/Universal Parks!!
Nov 17 – 24
Cottage in Kissimmee
4.81 out of 5 average rating, 68 reviewsUpdated Kissimmee Cottage near Disney (5 miles)
Aug 7 – 14
Cottage in Four Corners
4.7 out of 5 average rating, 23 reviews5 Bed Cottage in Margaritaville Close to Parks
Feb 25 – Mar 4
Cottage in Kissimmee
4.83 out of 5 average rating, 115 reviewsTiny house near Disney "Please be our Guest "
Oct 27 – Nov 3
Cottage in Kissimmee
4.74 out of 5 average rating, 133 reviewsSherwood Forest Vacation Home Near Disney
Oct 21 – 28
Cottage in Kissimmee
4.74 out of 5 average rating, 277 reviewsCute Sandcastle Cottage near Disney
Oct 1 – 8
Cottage in Kissimmee
4.95 out of 5 average rating, 38 reviewsMickey's Hideaway Cottage
Jun 26 – Jul 3
Destinations to explore
- Cottage rentals Orlando
- Cottage rentals Florida
- Cottage rentals Florida
- Cottage rentals Kissimmee
- Fitness-friendly rentals Osceola County
- Rentals with outdoor seating Osceola County
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- Rentals with an accessible height bed Osceola County
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