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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Winter Haven Cottages

Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
Family 4BR Home w/ Resort Pool Near Disney
House (4 Bedrooms) | Floor plan

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
Lake Ida Beach Resort
Porch

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (176)
"Good sized cabins. A bit best up but very comfortable. "
The price is CA $112
CA $125 total
includes taxes & fees
Aug 5 - Aug 6
Lake Ida Beach Resort
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Exterior

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay here! The house was well stocked with lots of games, movies, toys. All combined with the piano, foosball table, screened in porch and private backyard gave us plenty to do as a family with all ages. Everything was of very high quality and comfortable. We also really appreciated how responsive, friendly, and accommodating our hosts and their staff were. We will definitely stay here again!"
The price is CA $159
CA $384 total
includes taxes & fees
Aug 5 - Aug 6
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven Home w/ Pool Near Legoland!
Exterior

Winter Haven Home w/ Pool Near Legoland!

3.0 star property
6.0 out of 10, (2)
"Very spacious, clean and recently remodeled property. Very close to LEGO Land, great alternative to staying at Legoland "
Winter Haven Home w/ Pool Near Legoland!
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Outdoor dining

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Property grounds

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

9.8 out of 10, Exceptional, (48)
"We had a great stay! Very clean, spacious for a family of 4, easy access to Disney parks, food/shopping. Will definitely stay again! "
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Exterior

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Beautiful, family-friendly cottage just 4 miles from Disney World
Exterior

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 $117
CA $299 total
includes taxes & fees
Aug 5 - Aug 6
Beautiful, family-friendly cottage just 4 miles from Disney World
Townhome Splash Pool BBQ Free Water Park!
Miscellaneous

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
3148 Caribbean Soul Drive
Property grounds

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
3050 Pirate Way
Miscellaneous

3050 Pirate Way

3.0 star property
3050 Pirate Way
3000 Latitude Lane
Outdoor spa tub

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
8960 Cat Palm Road
Miscellaneous

8960 Cat Palm Road

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice place to stay. Clean, quiet, secure."
8960 Cat Palm Road
Mid-century Modern Escape in Central Lakeland!
Interior

Mid-century Modern Escape in Central Lakeland!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Communication with the host was simple and she was accessible. The basic amenities were readily available and we did not have to rush to go to the supermarket when we arrived. The place is spacious, clean and neighbourhood very quiet."
Mid-century Modern Escape in Central Lakeland!
~ 10 Mi to Animal Kingdom: Davenport Family Home
Interior

~ 10 Mi to Animal Kingdom: Davenport Family Home

3.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect two day stay for us … close to everything we n ended it to be. "
~ 10 Mi to Animal Kingdom: Davenport Family Home
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Pool

Elegant Family Home w/ Pool, Game Room, Themed Bedrooms

3.0 star property
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Disney, Universal and Legoland Getaway
Exterior

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is CA $94
CA $283 total
includes taxes & fees
Aug 9 - Aug 10
Disney, Universal and Legoland Getaway
Sleek Home Near Downtown Lakeland w/ Yard!
Interior

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (2)
Sleek Home Near Downtown Lakeland w/ Yard!
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

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"This was a quick but the property was nice and clean! We had connecting room which was convenient for out family of 7!"
marla 1-night trip
Posted 14 hours ago
Hilton Vacation Club Aqua Sol Orlando West