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Vacation Rentals in Winter Haven, Florida

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about Winter Haven

Winter Haven, Florida Vacation Rentals and Tourism

While Florida beaches preoccupy most tourists, the state’s many lakes ensure just as much summer fun! For a lakeside getaway with a distinctly Florida vibe, check out Winter haven vacation rentals. A Winter Haven, Florida vacation can be defined by many things, but you’ll probably spend some time by the water. There’s no escaping the lakes near your Winter Haven rental – you’ll be vacationing to a decidedly water-based community.

There’s a lot more than just lake recreation to keep you entertained in your Winter Haven vacation rental however. Cypress Gardens Adventure Park, the Fantasy of Flight vintage aircraft museum, and the Bok Sanctuary are some reasons that Winter Haven vacation rentals have such a strong draw. The restaurants in and around Winter Haven lodging are quite the treat as well, whether you’re looking for casual or gourmet dining.

It certainly can’t hurt to take a look at the Winter Haven vacation homes listed here. And once you stay in one, you’ll quickly learn why so many people are proud to call Winter Haven condos, homes, and cabins their permanent homes.

Winter Haven Vacation Rental Deals

If you are planning a trip to Winter Haven, don’t let your budget get in the way of staying in a nice, roomy place—stay in a cheap Winter Haven rental home. Choose from a wide variety of money saving Winter Haven houses, spacious and luxurious villas, and sizable – but reasonably priced – town homes. Because we accommodate the size of any budget as well as the size of any group, we're positive that you'll find a low-cost Winter Haven vacation rental perfect for your next vacation. Just be sure you get a chance to enjoy a fun day away from your Winter Haven lodging.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Winter Haven Lake Lulu Orlando Area Condo
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 3
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Lakehouse Vacation Home in Winter Haven Florida
Winter Haven House Rental Picture
  • bedrooms 3
  • community Lake Daisy Estates
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $125 - $175 /nt
    $900 - $1,250 /wk
    $2,300 - $2,500 /mth
 
 
 
 
 

15 reviews write a review

Relax In Winter Haven Orlando Screened Porch!
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

2 reviews write a review

Private, tropical getaway near Legoland & Disney
Winter Haven Apartment Rental Picture
  • bedrooms 1
  • community Winter Haven
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $400 /wk
    $1,250 /mth
 
 
 
 
 

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Beautiful Pool Home on Ski Lake
Winter Haven House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $1,200 - $1,600 /wk
 
 
 
 
 

21 reviews write a review

Beautiful Lake Ashton Golf Club - 3 BR 2 Bath Villa
Winter Haven House Rental Picture
  • bedrooms 3
  • community Lake Ashton
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $3,000 /mth
 
 
 
 
 

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Lake Rochelle Rental (Lakefront)
Winter Haven House Rental Picture
  • bedrooms 3
  • community Rochelle Gardens
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $2,200 /mth
 
 
 
 
 

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Lake Howard Waterfront Lake House Winter Haven Fl
Winter Haven House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $550 - $850 /wk
    $950 - $1,900 /mth
 
 
 
 
 

1 reviews write a review

Huge Winter Haven Orlando Area On Lake!
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,399 - $2,399 /mth
 
 
 
 
 

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4070 Lake Marianna Dr lakefront
Winter Haven House Rental Picture
  • bedrooms 3
  • community Auburndale
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 3
  • rates (USD) $1,000 /wk
    $3,000 /mth
 
 
 
 
 

2 reviews write a review

Affordable Winter Haven Orlando Area
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Stay in Fabulous Lake Ashton Gated Adult Community
Winter Haven House Rental Picture
  • bedrooms 3
  • community Lake Ashton
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $1,350 - $2,400 /mth
 
 
 
 
 

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Relaxation In WInter Haven Orlando Area
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Winterset/Winter Haven/Central FL
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community Garden Villas
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $1,295 - $1,895 /mth
 
 
 
 
 

3 reviews write a review

Moon's Fish Camp
Winter Haven House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $150 - $200 /nt
    $700 - $900 /wk
    $2,600 - $3,000 /mth
 
 
 
 
 

1 reviews write a review

1 bedroom vacation rental
Winter Haven Apartment Rental Picture
  • bedrooms 1
  • community
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $305 - $395 /wk
    $1,050 - $1,125 /mth
 
 
 
 
 

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Lake Ashton Community
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community Lake Ashton
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,500 /mth
 
 
 
 
 

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Winter Haven Apartment Rental
Winter Haven Apartment Rental Picture
  • bedrooms 3
  • community
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $400 - $500 /wk
 
 
 
 
 

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Winter Haven Two Bedroom Rental
Winter Haven Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $350 - $400 /wk
 
 
 
 
 

1 reviews write a review

Chain Of Lakes Pool Home With Beach And Boat House
Winter Haven House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 18
  • baths 5
  • rates (USD) $250 - $500 /nt
    $1,750 - $2,300 /wk
    $6,600 - $9,000 /mth
 
 
 
 
 

9 reviews write a review

One of the cleanest spring fed lakes in Florida, located between Tampa & Orlando
Winter Haven House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $199 - $249 /nt
 
 
 
 
 

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***FANTASTIC DOWNTOWN CONDO Near LEGOLAND w/2/FIREPLACES***
Winter Haven Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $115 /nt
 
 
 
 
 

23 reviews write a review

10 minutes to lego land 45 minutes to hard rock casino
Winter Haven Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $200 - $250 /nt
    $1,000 /wk
    $3,000 /mth
 
 
 
 
 

3 reviews write a review

Affordable Winter Get Away. Apartment. Clean & Comfy & Quiet
Winter Haven Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths
  • rates (USD) $887 /mth
 
 
 
 
 

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