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Browse Select Winter Haven Cottages

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

3.0 star property
10.0 out of 10, Exceptional, (3)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
The price is CA $197
CA $499 total
includes taxes & fees
Aug 22 - Aug 23
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (177)
"We have stayed here several times. "
The price is CA $99
CA $111 total
includes taxes & fees
Aug 22 - Aug 23
Lake Ida Beach Resort

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
10.0 out of 10, Exceptional, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
The price is CA $159
CA $386 total
includes taxes & fees
Aug 22 - Aug 23
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Luxury Cottage Near Legoland & Chain of Lakes

10.0 out of 10, Exceptional, (6)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
The price is CA $139
CA $284 total
includes taxes & fees
Aug 26 - Aug 27
Luxury Cottage Near Legoland & Chain of Lakes

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
The price is CA $90
CA $280 total
includes taxes & fees
Aug 25 - Aug 26
Jedi cottage 4 miles from Disney! Mins from universal!

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is CA $104
CA $299 total
includes taxes & fees
Aug 23 - Aug 24
Disney, Universal and Legoland Getaway

Hidden Lake View Cottage 5 miles from Disney!

9.0 out of 10, Wonderful, (2)
"Awesome"
The price is CA $104
CA $299 total
includes taxes & fees
Aug 23 - Aug 24
Hidden Lake View Cottage 5 miles from Disney!

161 - 4 bed Gem at Terraverde Resort

The price is CA $372
CA $710 total
includes taxes & fees
Aug 24 - Aug 25
161 - 4 bed Gem at Terraverde Resort

Beautiful, family-friendly cottage just 4 miles from Disney World

9.4 out of 10, Exceptional, (11)
"Perfect for our stay in Orlando/Kissimmee. Close to everything we were attending, quiet, clean, and well supplied with the basics."
The price is CA $118
CA $297 total
includes taxes & fees
Aug 25 - Aug 26
Beautiful, family-friendly cottage just 4 miles from Disney World

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
The price is CA $111
CA $318 total
includes taxes & fees
Aug 28 - Aug 29
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Perfect Place for a Perfect Vacation

3.0 star property
The price is CA $132
CA $288 total
includes taxes & fees
Aug 26 - Aug 27
Perfect Place for a Perfect Vacation

Family-Friendly Cottage Near Orlando’s Top Attractions

The price is CA $125
CA $282 total
includes taxes & fees
Aug 24 - Aug 25
Family-Friendly Cottage Near Orlando’s Top Attractions

1209-9-b -mansion Themed With Pool Near Disney

The price is CA $796
CA $1,771 total
includes taxes & fees
Sep 2 - Sep 3
1209-9-b -mansion Themed With Pool Near Disney

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

4.0 out of 10, (1)
The price is CA $94
CA $210 total
includes taxes & fees
Aug 23 - Aug 24
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

5180 Spectacular 5bd4ba- Private Pool&spa

The price is CA $443
CA $898 total
includes taxes & fees
Aug 24 - Aug 25
5180 Spectacular 5bd4ba- Private Pool&spa

411 Wanderlust Heaven 5bed/pool

The price is CA $596
CA $1,128 total
includes taxes & fees
Sep 1 - Sep 2
411 Wanderlust Heaven 5bed/pool

Pool & Lazy River: Windsor House 9 Mi to Disney!

3.0 star property
The price is CA $225
CA $757 total
includes taxes & fees
Aug 24 - Aug 25
Pool & Lazy River: Windsor House 9 Mi to Disney!

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.

2.0 star property
The price is CA $265
CA $652 total
includes taxes & fees
Aug 27 - Aug 28
Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

The price is CA $265
CA $652 total
includes taxes & fees
Aug 27 - Aug 28
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.

The price is CA $265
CA $652 total
includes taxes & fees
Aug 27 - Aug 28
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Haven Hotel Reviews