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