Vacation Rentals in Winter Haven, Florida

50 Properties Available

Waterfront-Heated SaltWtr Pool-Putting Green-Beach-FirePit-Dock-Sunsets-Legoland Private vacation home
Waterfront-Heated SaltWtr Pool-Putting Green-Beach-FirePit-Dock-Sunsets-Legoland
$808 / night
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Spectacular Waterfront Home in Winter Haven Private vacation home
Spectacular Waterfront Home in Winter Haven
$756 / night
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Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families! Private vacation home
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
$563 / night
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Fantastic Water Front Home on the Chain of Lakes Private vacation home
Fantastic Water Front Home on the Chain of Lakes
$502 / night
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Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun Private vacation home
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
$441 / night
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Lakefront Winter Haven Retreat: Hot Tub & Patio! Private vacation home
Lakefront Winter Haven Retreat: Hot Tub & Patio!
$421 / night
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You'll find all the newest upgraded services at our room !! Private vacation home
You'll find all the newest upgraded services at our room !!
$414 / night
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Lake Hamilton Hideout Private vacation home
Lake Hamilton Hideout
$409 / night
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Lakefront Vibes w/ Lanai! Bird-Watching Paradise Private vacation home
Lakefront Vibes w/ Lanai! Bird-Watching Paradise
$403 / night
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Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome Private vacation home
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
$401 / night
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Peaceful Lakeside Retreat Private vacation home
Peaceful Lakeside Retreat
$399 / night
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Family Winter Haven Retreat w/ Pool & Game Room Private vacation home
Family Winter Haven Retreat w/ Pool & Game Room
$297 / night
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3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724 Private vacation home
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
$283 / night
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Lake life living 45 mins from most central FL theme parks... Private vacation home
Lake life living 45 mins from most central FL theme parks...
$268 / night
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Lake Shipp House with pool and dock on the water Private vacation home
Lake Shipp House with pool and dock on the water
$251 / night
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2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND. Apartment
2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.
$248 / night
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Cozy Lakefront Home w/ Pool -7 mins from Legoland Private vacation home
Cozy Lakefront Home w/ Pool -7 mins from Legoland
$244 / night
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Lakefront 2 story 4\/2 bungalo with huge yard. Private vacation home
Lakefront 2 story 4\/2 bungalo with huge yard.
$239 / night
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Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready! Cottage
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
$239 / night
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Pet Friendly Home 2 Miles from Legoland\/Peppa Pig Water Park - Privately Fenced Private vacation home
Pet Friendly Home 2 Miles from Legoland\/Peppa Pig Water Park - Privately Fenced
$237 / night
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Charming Home on the Lake. Private vacation home
Charming Home on the Lake.
$225 / night
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Staybridge Suites Winter Haven Auburndale by IHG Hotel
Staybridge Suites Winter Haven Auburndale by IHG
$223 / night
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8 Mi to Legoland: Winter Haven Home w/ Lanai! Private vacation home
8 Mi to Legoland: Winter Haven Home w/ Lanai!
$222 / night
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Chanti’s Place, Winter Haven. Great Longterm Stay Private vacation home
Chanti’s Place, Winter Haven. Great Longterm Stay
$202 / night
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Private King Suite with W/D near LEGOLAND & Winter Haven Hospital Apartment
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
$177 / night
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Cozy 1-Bedroom Retreat Near Downtown & Legoland Apartment
Cozy 1-Bedroom Retreat Near Downtown & Legoland
$175 / night
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StayComfy at WinterHeaven Private vacation home
StayComfy at WinterHeaven
$166 / night
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4 Mi to Legoland: Newly Built Home in Winter Haven Private vacation home
4 Mi to Legoland: Newly Built Home in Winter Haven
$160 / night
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Lakefront condo\n55+ community Condo
Lakefront condo\n55+ community
$147 / night
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Lake House to be leased with Main house: 2042348 Private vacation home
Lake House to be leased with Main house: 2042348
$139 / night
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1-bedroom Apartment C near Hospitals/Legoland/Chain of Lakes Apartment
1-bedroom Apartment C near Hospitals/Legoland/Chain of Lakes
$134 / night
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Legoland on The Lake Gem!Close to Disney! All you need in one place! Cozy&Lovely Apartment
Legoland on The Lake Gem!Close to Disney! All you need in one place! Cozy&Lovely
$125 / night
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Charming Home 5 Minutes From Legoland Private vacation home
Charming Home 5 Minutes From Legoland
$115 / night
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Holiday Inn Winter Haven, an IHG Hotel Hotel
Holiday Inn Winter Haven, an IHG Hotel
$110 / night
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Winter Haven Apt: 1 Mi to Polk State College! Apartment
Winter Haven Apt: 1 Mi to Polk State College!
$107 / night
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Fully Furnished 3BR Home- Extended Stay-Winter Haven Private vacation home
Fully Furnished 3BR Home- Extended Stay-Winter Haven
$103 / night
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TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital! Private vacation home
TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!
$98 / night
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Howard Johnson by Wyndham Winter Haven FL Motel
Howard Johnson by Wyndham Winter Haven FL
$89 / night
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Lake Ida Beach Resort Cottage
Lake Ida Beach Resort
$79 / night
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Studio Apartment in Winter Haven, FL Apartment
Studio Apartment in Winter Haven, FL
$78 / night
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Rodeway Inn And Suites Motel
Rodeway Inn And Suites
$70 / night
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Econo Lodge Winter Haven Chain Of Lakes Hotel
Econo Lodge Winter Haven Chain Of Lakes
$67 / night
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4 Mi to Legoland: Newly Built Home in Winter Haven Cottage
4 Mi to Legoland: Newly Built Home in Winter Haven
$0 / night
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5 Bedroom Chain of Lakes Home w\/AC Pet Friendly Private vacation home
5 Bedroom Chain of Lakes Home w\/AC Pet Friendly
$0 / night
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Beautiful 2bedroom near LEGoLAND Private vacation home
Beautiful 2bedroom near LEGoLAND
$0 / night
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Charming bed & breakfast in wonderful Winter Haven with WiFi, fitness room Bed & breakfast
Charming bed & breakfast in wonderful Winter Haven with WiFi, fitness room
$0 / night
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Lakefront Winter Haven Retreat: Hot Tub & Patio! Cottage
Lakefront Winter Haven Retreat: Hot Tub & Patio!
$0 / night
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PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida Private vacation home
PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida
$0 / night
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Peace & Love Room 5 minutes from Winter Haven Hospital Private vacation home
Peace & Love Room 5 minutes from Winter Haven Hospital
$0 / night
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Relaxing location To 10 minutes Legoland , 40 minutes Disney word Private vacation home
Relaxing location To 10 minutes Legoland , 40 minutes Disney word
$0 / night
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